111: Katie Jane Bailey is Living the Disco Lifestyle on a World Class Sales Team at Figma

0:00 Scott Ingram: This episode is brought to you thanks to the generous support of Proposify, Terryberry, and Alyce. To learn more about them and all of our sponsors who have invested in you and this community, just click over to top1.fm/sponsors. You're listening to the Sales Success Stories podcast, where we deconstruct world-class sales performers to provide insights and strategies to help you improve To learn more, visit us at top1.fm. Here's your host, Scott Ingram. Today on the Sales Success Stories podcast, my guest is Katie Jane Bailey. Katie Jane is the top enterprise account executive at Figma out of San Francisco. Welcome to the show, Katie Jane.

0:49 Katie Jane Bailey: Thanks, Scott.

0:50 Scott Ingram: Before we get into this, I just want to thank your manager, Marissa Fuhr. Marissa is a fan of the show and clearly a huge fan of yours, Katie Jane. She sent me the most incredible email recommending you and Brad. Bragging about how you had orchestrated the biggest deal in company history last quarter. And I'm just, I'm really excited to dig into this. Thanks.

1:10 Katie Jane Bailey: Oh my gosh, I'm so appreciative of Marissa for submitting this. I am so excited to be here.

1:17 Scott Ingram: Awesome. Well, let's start like we always do with some immediate value and talk about the top 3 things that you believe have contributed the most to your success in sales. What are those?

1:27 Katie Jane Bailey: Yes, number one is I think I am most successful because I'm not afraid to have difficult conversations with my customers and introduce friction into the relationship.

1:38 Scott Ingram: Excellent. So, what's an example of that kind of friction? Like, where might that show up?

1:43 Katie Jane Bailey: Yes, so I sell Figma, which is a SaaS platform. We're a design platform, and we have a lot of trials as part of our sales process. And oftentimes a trial is expiring, but the paperwork is not complete yet, and I have to engage in that difficult conversation of, let's say my customer's name is John. Hey John, you know, we don't have approval to move forward with this trial because we haven't heard from your procurement team in 4 weeks. And so until I see movement here, then we're not able to, you know, continue working on this with you. And that's super hard because you're essentially upsetting your, your client. You're introducing friction. They might not like me as a salesperson because I'm telling them no to a trial extension, but having done this for a little while, I think that friction actually creates intimacy with my customers. And I find that it can be a really good thing in terms of, you know, really calling people to take action, delivering on the promises they've, you know, they've given me and basically holding them accountable. And sometimes those are difficult conversations to have, but I have to go into it knowing that, you know, my customer is not They're not buying like a relationship with me. They are buying Figma. And my job is to help them get Figma on the timeline that they need. And if I go into it with that attitude, then I'm able to essentially help deliver value, but, you know, kind of get them to the table. Does that answer your question?

3:18 Scott Ingram: Yeah, absolutely. I think that context is really helpful. And you said the word I was thinking, it's, it's holding your customers accountable, which isn't always easy.

3:25 Katie Jane Bailey: Yeah, exactly. I think that in sales, we want people to like us as people, and so We want to say yes to our customers every single time. Like we want whatever they ask for, we want to give that to them. But sometimes saying yes is not actually going to get the deal done faster, or you don't have the resources to say yes. And so at Figma, we actually say no kind of a lot. And the reps who are successful are able to say no confidently, empathetically, of course. You know, you're not like, no, sorry. You, you approach it of, I really wish I could help you with this, but I'm just not able to. It really. Asks more of your customer in the process, and I see really good results from it.

4:08 Scott Ingram: Fantastic. What's the second thing?

4:10 Katie Jane Bailey: Second thing is I have a very natural curiosity. My dad taught me the term lifelong learner, and not only does this mentality translate into my sales process, I like to say discovery is a lifestyle, not a stage. I'm curious with my customers. Where does this impact your business if we get this done this quarter? You know, how, who else do we need to talk to? So there's not only a curiosity in terms of the deal and continuing to ask questions the entire cycle. But also, and this is something that Marissa has instilled on our team, is our whole team is reading books all the time, sales books all the time, listening to this podcast. And, you know, I'm taking a sales course in February. Like, just seeing that learning how to do your job better actually makes you do your job better. So I think curiosity, it plays out in a lot of different ways.

5:02 Scott Ingram: That's fantastic. And the quote is brilliant. Discovery is a lifestyle. Not a stage. Well, I think I resemble that given how long these interviews can be sometimes. So, I certainly understand that. What's, what's the course that you're taking?

5:15 Katie Jane Bailey: It's the Winning by Design course. Are you familiar with that one?

5:18 Scott Ingram: A little bit. I've heard of it. I've not gotten into it deeply.

5:21 Katie Jane Bailey: Yeah, I have only explored it a little bit through a colleague of mine, and it just is very succinct and seems very powerful. Like, for example, on a demo, they talk about kind of the attention span within a demo. So, like, it spikes at the beginning and then it kind of in the middle, like, slows down, right? Because you're… it's a long time. And so, how do you bring that customer's attention back with questions like, Scott, is this relevant to you? You know, things like that that ask them to not only engage of, do you like this? But also, does this apply to your, your workflow? And so, I'm really excited about the course.

5:58 Scott Ingram: You know what? I may be more familiar with that than I thought. Do they typically position that more for kind of solutions engineers, sales engineers than they do us regular sales folks?

6:10 Katie Jane Bailey: Us regular sales folks? I don't know, actually. I'm really new to it. So yeah, I think it's all psychology-based, actually. I know on their website it's a lot of, it's like SDRs, AEs, and manager training, but I'm super excited about it.

6:24 Scott Ingram: Well, I might be confusing it with something else, but something for us all to go check out. As always, we will have links to all of that stuff. So Winning by Design will be the first thing. That you'll find a link to if you go to top1.fm forward slash. Oh, this is going to be complicated. You have multiple names and we're going to have to add a dash. So it'll be Katie-Jane-Bailey, or I think I'm going to be right about the number here, top1.fm forward slash 111. 111.

6:51 Katie Jane Bailey: Nice.

6:52 Scott Ingram: That's a lot of ones. You're number one.

6:53 Katie Jane Bailey: I love it.

6:54 Scott Ingram: So what's number 3? So we've got, you're not afraid to have difficult conversations and introduce that friction. You have this natural curiosity. You're a lifelong learner. Discovery is a lifestyle. What's number 3?

7:06 Katie Jane Bailey: Yeah, number 3 is I'm a natural performer and I'm a natural hostess, actually. I love to host dinner parties. I love to host people at my house. And sometimes when I think about my relationship with my customers and how I go into even just that first conversation, I'm totally performing, but I'm also hosting them. You know, it, it's almost like, hey, you came into Figma's, you came into our, our house, have a seat. What can I get you to drink? And how can we help you get what you need? And I know that is such a funny way to describe a sales style, but I think it, it actually is what helps me to be successful is that people, I think they've, you know, I, I like to make people feel very welcome.

7:48 Scott Ingram: Well, and clearly it's something that's natural for you and, and you're leaning into it and you come to sales from kind of a non-traditional background that ties this all together. What, what is that?

8:00 Katie Jane Bailey: Yes. So, I actually started my career in musical theater in, in New York City. So, I performed professionally singing and dancing all over the world for 4 and a half years and loved it. It was incredible. I think it really shaped who I am today, and I wouldn't trade all the money in the world for my time in musical theater. I think it gave me a lot of the skills that I needed to be successful in sales.

8:26 Scott Ingram: So, how does one go from musical theater to tech sales?

8:31 Katie Jane Bailey: Yeah, it's such a natural transition, right, Scott?

8:34 Scott Ingram: Of course. So obvious.

8:36 Katie Jane Bailey: So obvious, everybody. So, yeah, so it's such a fun question. So in musical theater, and your job is auditioning and vacation is performing. So what does that mean? Right? So when you graduate, so I went to school for musical theater at Oklahoma City University. It's kind of this like very, very competitive musical theater school. You graduate, you move to New York. If you know the musical Annie, 3 bucks, 2 bags, 1 me, like that is actually me. And I arrived in New York and you basically hit the ground running and you go to auditions every single day. And an audition ranges from a dance call where you're learning like choreography and performing that to walking in, giving accompanist at the piano your music, singing a song, and wondering if you get a callback. So that was my life essentially, is even when you book a gig, and I was very lucky to book many gigs, you are still auditioning while you are performing because You always have to think about that next job. There's no such thing as like, oh, this is my annual income on my salary. It's like, oh, this is a 10-week gig and it ends August 1st and I'm back to my survival job. So I loved it so much. And after a while you start to look around and say, is this the life that I want? Is this how I want to raise a family? Or is Do I want to have this kind of unsteady income forever? And when I took a look at my values, just me, Katie Jane, I started to recognize that that lifestyle did not match the values that I wanted to live by. And so there's this like kind of very haunting phrase when you're in theater, which is, if you can do anything else, do it. And so when you're in it, you're like, I can't do anything else. This is it. I can only be an actress. And then one morning I woke up and And I realized I can do something else. And it was a really scary moment. I had the actually fun opportunity to give a talk on this at Figma. I can send it to you actually if you're interested, but it basically, I went through a series of personality tests to say, okay, I'm 27. I have no professional experience except singing and dancing, and I have no idea what to even do. In a career, and I realized that sales was actually very, very similar to auditioning. And auditioning, you walk into a room, you pitch a product, you hear no every single day, and you keep on going. And in sales, you open, maybe it's Zoom, you go into a room every day, you pitch a product, and that product is something that someone else has built. It's not you yourself. And you find you have to be creative. You have to be a good listener. You have to have improv. Skills. And so I started applying for sales jobs and I got 3 interviews and I got all 3 jobs as a BDR. And I got hired at this company called Parsley. Shout out to Parsley in New York. And I basically was like, I just need some at-bats. Like someone just give me a chance to just do this. I think I can do it really well. And after, you know, I think it's like 5, 6 years later, turns out I could do it and turns out I really love it. And yeah, that's kind of the story. That's how I got here.

12:01 Scott Ingram: I have so many questions. Do you find that the rejection in sales is easier because it's about a product and it's not a direct rejection of you?

12:13 Katie Jane Bailey: Oh yeah. Oh my gosh. My first ever phone interview for a sales job, they asked me how I handle rejection and I just, I couldn't help but laugh on the call. I was like, oh, I handle it very well. Thank you. And so, yeah, I mean, I think I think it helps because I'm able to disengage from them, someone saying no to the product, and it helps me to have a lot more empathy for my product team because what they are building is what I'm putting in front of people, and I know how vulnerable that is. So yeah, it definitely has shaped rejection in sales versus musical theater for sure.

12:57 Scott Ingram: Yeah, it's, it's really fascinating how frequently this disengagement theme is, is showing up in, in these lives. Number of of episodes. Similarly, I wonder if are you acting when you're selling?

13:10 Katie Jane Bailey: Oh, absolutely. There are times where you know some of these negotiations that you go into, there you gotta have a straight face, you know, and you're kind of watching it happen while you're while you're doing it. At least I am. And so you're you're playing a role essentially, and you're. You know, maybe you go into it with one stance and you just have to hold the line. We talk about that a lot at Figma, holding the line with our customers. And yeah, I go in and I'm like, the role I'm playing today is I'm the top negotiator of if you would like to purchase enterprise licenses at Figma, this is what we're offering and this is what we're going to talk about, you know? And it's like that, that's the character that I take on and it really serves me well. It's, it makes it so fun too. There's so many times I finish a call and I just start laughing because it's like I come off stage, you know?

14:04 Scott Ingram: Gosh, that is so great. And I think one of the really interesting things that you said, people in sports and things will talk about, you know, once you have enough experience, the game slows down. And this idea that you're able to kind of see it from outside of yourself, and it really sounds like that's kind of the place that that you're at. Like, okay, I see everything that's going on. I see what you're doing. I see what I'm doing. And yeah, and it sounds like it's kind of slowed down for you and gotten to that place. Thank you.

14:33 Katie Jane Bailey: That feels like a huge compliment, Scott. I'm like, that is how it feels. Yeah, it's so fun, you know, like it's probably some of my favorite times in sales are in those types of calls where you're just watching all the players play their role, you know?

14:48 Scott Ingram: Yeah. Yeah. That's the thing where The sales journey, the sales career is such a fascinating thing, right? Because the early stages are, I don't think they're easy for anybody. I think they're just hard. You have to go through this struggle and this challenging place and kind of figure this out. But if you do it right and you really work at it, it gets more and more fun.

15:14 Katie Jane Bailey: Oh, I totally agree. Yes. Yes. 100%. Yeah. I think that one thing that I love to think about, especially in like hiring or adding to a team, is, you know, I have this super non-conventional background in sales, but my non-conventional background allowed me the, the grit to get through those really hard first couple of years until you kind of break through the surface, you know? And I am so thankful to Parsley for giving me that, that opportunity to actually do it. But you're exactly right. If you can just get through because what we do is hard and it gets easier, but it's still hard, you know?

15:52 Scott Ingram: Yeah. How long were you in sales before you started to feel like, I'm really getting this?

15:58 Katie Jane Bailey: Yeah. When I was riding the elevator up to the 7th floor for my first job, in my head, I literally thought to myself, can I actually do this? And I didn't know. I genuinely had no idea, but I was like, well, I'm gonna sure give it a try. So, I would say it was pretty quick that I felt so comfortable. I think that there's a difference between I can do this and I am doing this really well. So, it was within the first year at my first job in sales that I realized, hmm, I can, I can really do this. I can be very successful with this and I really enjoy this, but it's It's those, in dance ballet, it's like your peas and carrots. And if you can't do your tendus and pliés, you can't do your, you know, battements and grand jetés. So it's like you can't run before you walk kind of thing. And for me, I realized that I had this natural joy and desire to be closing deals and doing all these things, but I didn't have those fundamental skills. And that's what ultimately slowed me down. And I would say that Gosh, I mean, even in the last 2 years, I just, I don't know, I see leaps and bounds in myself of every year I feel like, oh, I'm doing this well. I'm doing this better and better. So that's kind of a long answer to your question, but I do think that there's a difference there.

17:22 Scott Ingram: Yeah, I think it's a great answer. Well, let's go back and kind of pick up some contextual pieces. You've dropped some hints along the way around what Figma is. Why don't you just kind of Talk about what is your role? What's your territory? You know, what is Figma? Who are you selling to? All that kind of stuff.

17:38 Katie Jane Bailey: Yeah, totally. So Figma is a design platform. What that means is we are a SaaS product that designers create products in. So imagine like the Uber app, right? That if you just create the design, it's a collection of squares, shapes, text, and colors, and designers are creating hundreds of different iterations of these products before it actually becomes, before it reaches your phone essentially. And so Figma is a platform that designers create, iterate, collaborate on to create these designs. Figma is, we just turned 5 recently. We sell to design teams. So that would be like a group of UX/UI designers. Design is becoming more and more important for a company's bottom line. So think about the difference between Uber and Lyft, and in your head you picture 2 different designs, right? One is, one is fast and speedy and slick, and one is clunky and a little slower. And I'll let you pick which one is which, but design changes your experience with your product. Another example is like a bank. You no longer go into a teller and do all of your transactions there. It's on your phone. And so if you have a really smooth experience on that app, you're probably going to be a happier customer. And so we sell to designers and anyone who is creating digital products. We, as I mentioned, we're 5 years old, but our enterprise product is actually only 2 years old. And so we are really early stage. I am a senior account executive. I work with companies. We're a little bit still wild, wild west, but narrowing in on a more structured flow. So the funny thing is that the way that our territory is split up right now is EMEA and the rest of the world. And so I am in the rest of the world territory, which is North America, South America, APAC. And I work with companies that are, we split it up as 1,000 employees or higher is the enterprise territory. And there was one other question you had in there that I can't remember, but that's a, that's a quick kind of bring you up to speed with what I do.

19:51 Scott Ingram: That is perfect. And this is so weird. I just had. This real-time recognition. So we are working on designing an app. So stay tuned. And yesterday, so my… I have an in-house design team and the dev shop we're working with, shout out to DevScale, asked us… so we're working on kind of the front-end design for them and we were asking, well, what's the best way for us to deliver the design to you for you to work with? And they said, oh, we want it in Figma.

20:21 Katie Jane Bailey: No way.

20:22 Scott Ingram: I did not connect those dots until just now. I'm like, wait a minute.

20:25 Katie Jane Bailey: Oh my gosh. So you know Figma, you're a pro.

20:28 Scott Ingram: Yeah, well sure. I, we heard the name yesterday and now we gotta go figure it out.

20:32 Katie Jane Bailey: But that's fantastic. Oh my gosh.

20:33 Scott Ingram: Now I, now I know people, so this process will be so much easier.

20:37 Katie Jane Bailey: I love it. Yep. That's awesome.

20:39 Scott Ingram: Wow.

20:39 Katie Jane Bailey: And you're building an app. I love that.

20:41 Scott Ingram: Oh, just wait. There is big stuff coming. So if you're listening and you're interested in what it is that we are building, you should join the listener list cuz that's the best place to get that stuff. So go to top1.fm/111, get all the notes and all the links and all the cool stuff that Katie Jane's talking about. And then give us your name and email address and get on that list and find out all the cool stuff that we're working on. It's coming. I can't wait.

21:06 Katie Jane Bailey: That is so cool. Well, you're going to have great design because it's going to be done in Figma. So I'm 100% confident it will be very successful.

21:13 Scott Ingram: There you go. There you go. And now why don't we put your results in context? What did you do last year?

21:20 Katie Jane Bailey: Yes. So last year I led the largest ever deal for Figma in Figma's history and closed it out in Q3. I think that's a, is that what you're referencing, Scott?

21:34 Scott Ingram: Yeah. Yeah. Well, and not, not just that deal, but you had a pretty incredible year. You ended up on top. So what did that look like? What does it take to be number one at Figma?

21:43 Katie Jane Bailey: Ah, yes. So, oh my gosh, so many fun things happening at Figma. So one of those fun things is number one is kind of a Do you know the book Who Moved My Cheese? It's kind of like a Who Moved My Cheese. Number one is we have this really fun way of, okay, this person closed the highest revenue, this person closes the largest deals, this person has the highest close rate, and we celebrate all of these number ones essentially. And so I am number one with closing the largest deals at Figma. And yeah, and I've been able to perform above 200% for the last couple of quarters. And closed out just an incredible year of some really exciting big companies helping to grow the team from 2 to 10. Yeah. And, and just really pioneering a lot of deals that specifically this, this one pioneering a deal that really called Figma to be, it called us to mature a little bit. It called us to really rise to the occasion. And it was kind of, it was the story of, can we actually do it? And I don't want to spoil the story. Surprise, but we did it.

22:54 Scott Ingram: Well, and I want to totally dissect that deal. One of the bits of constructive criticism I've gotten about the show is some people come in with the expectation that, well, the show is called Sales Success Stories. I thought you were going to talk about a specific sales success and about that deal rather than the, the story of Katie Jane. And today I think we can have our cake and eat it too. Let's do it and talk through, talk through this deal. So I'm just going to let you kind of take it away. Where did this start? Give us some good level of detail and kind of blow-by-blow of, of how this thing came together. Cause I know there were all kinds of, of ups and downs and challenges, and you got to ride the emotional rollercoaster that is big deal sales. So walk us through it all.

23:41 Katie Jane Bailey: Yes. Yes. Okay. This deal is so fun. When you told me that we were going to deep dive, I'm honestly really excited because There's so many good stories to dig into. So let's set the stage. This deal was with one of the largest companies in the world, north of a quarter of a million employees. We have 280 employees at Figma. We launched our enterprise platform in February of 2019, and this deal started in August of 2019. A few other things to note about this customer is that they are highly regulated and they have very strict security controls. I'm sure everyone listening is seeing like flashing red of security reviews coming before their eyes, and that definitely delivered on this deal. And it was a year-long sales cycle and there were many players that were involved, many twists and turns. And that's kind of the, that's like how we set the stage. So is that, is that a good enough setting to dig in, Scott?

24:45 Scott Ingram: I think so. I think so. Let's go through it.

24:47 Katie Jane Bailey: So yeah, so it starts with actually an inbound to Figma. I was very fortunate to receive that inbound, and this was August of 2019. The request… so I'm going to kind of help you understand more about Figma as we go along, because that is a really important part of the story. So Figma is a huge bottoms-up platform. We have champions who will live and breathe Figma, and it is so fun to sell to those types of people. The inbound that I received And let's name this person Monica, was not one of those champions. So this person was curious, tell me about this, this product that a lot of people are talking about. Very, very slow. And at that time we were fielding inbounds that they ranged from, we need 2 licenses to, you know, 500 licenses or something like that. And it was just this crazy, where do we go with these deals? And keep in mind that we'd only been doing the sales motion at Figma for like 8 months at that point. So, very, very young. We were still identifying what is our sales cycle. I mean, we're still doing that today. What are the success criteria? How do we drive a deal forward? And so, with this lead, I took the approach of, I'm going to match the exact energy you bring to me, and I'm just going to, I'm going to walk with you through this. So, I, I don't even think I opened an opportunity. I just said, let's just have some conversations. And one conversation kept leading to the next, but no real buying urgency. Nothing that was like, oh, we need this now. Fast forward to October. So, a couple of months in, we are hosting an event in New York and hosted by Google. Some of our customers that were speaking at the event, New York Times, Google was speaking, and Goldman Sachs. And this Monica joined me and I made sure to introduce Monica to some of the speakers and say, I think it's important that you talk to other people who are, who are in a similar position to you. And that was a tipping point and it kicked off a trial of Figma. We had a lot of success with this trial and that is honestly the easiest part of selling Figma is getting buy-in from a team that is designing. So after 2 months, the team was sold. They drank the Figma Kool-Aid. They were like, yep, this is the direction we need to head. And so my champion and I are looking down this, you know, dark alleyway of who knows what's coming from a purchasing process with a company of this size and these kinds of regulations. And Figma had never done a deal like this before. So we said, we were very transparent. We said, you know, there's, this is going to be a process that we're going to have to, we don't know if when we get to the end of this, if we can actually accommodate your request. This, but we're willing to try. So let's, let's kick the tires. So the first meeting, which is one of my favorite ever sales meetings, and this is totally going back to me, the room is slowing down and I'm, I'm like watching myself in this conversation. So I was in London, my champion says, I want you to meet this person, they're going to help expedite this deal. And so I go and meet this person who is in procurement and they take me, they are 15 minutes late to pick me up from downstairs. They take me to a private coffee shop on one of the higher floors, and this person says to me, so am I negotiating with you? And I said, why yes you are. And it was this immediate like, oh, I see what's happening. We're just intimidation 101 here. And the whole 30 minutes of coffee was this very large company saying, we want Figma now, and these are the conditions we're able to do it. And Figma is a little bit of a rare breed. We don't discount. We have certain parts of our contract that we will not agree to. Like, for example, like, this is so specific, but one invoice, right? So you have this massive company and Figma says, we'll give you one invoice. And And it's just this like wild set of circumstances that if you're doing a wall-to-wall rollout of Figma, it makes perfect sense. But if you only want it for a couple of teams here and there, then this company is going to fight it. And so this customer is livid in this conversation. And this is where I talk about having the difficult conversation, not being afraid to introduce friction, hold the line, stand by the value that I know Figma offers. And it results with him ending the conversation saying, do you know who we are? We are, and inserts the name of the company. And I said, and I think that is so great and we would love to work with you guys, but these are the terms that we're gonna be able to do it. So it was this like bizarre negotiation before the negotiation had even started. And it was like the tipping point of, okay, this is the direction. We're headed. I could go on forever. Any like questions, thoughts? Keep going.

30:02 Scott Ingram: So the thing that is coming to mind is this feels so much like… there's, there's a guy who writes about this and does, does a really good job of it and kind of understanding just the, the positioning and all that's going on with this. I'm not a giant fan of the approach, but the book is fantastic. He's got this killer newsletter. So Oren Klaff is, is the guy I'm thinking of. So some of the listeners I'm sure are familiar, and he wrote book called Pitch Anything, I think is, is the name of his book. Again, we'll, we'll link stuff up in the, in the show notes. There's a lot in his… he was one of these just like giant deal negotiator kind of guys. And there's a lot of this stuff that goes on. There's a lot of this, this framing type of stuff. So if you're interested in this, you want to go a little bit deeper, I think that's a great, great resource to kind of learn more. The other thing that, that's coming to mind for me is I actually think it's so much easier and kind of empowering when you keep things simple for a sales team and you're like, no, just don't discount.

31:08 Katie Jane Bailey: Yes.

31:08 Scott Ingram: Or in my case, you know, I work for a professional services organization. We have just… it's just a schedule. The more you buy, the better your discount is. So if you want more of a discount, just buy more. Yeah, very simple. It's very linear. Nothing else moves.

31:23 Katie Jane Bailey: Yeah.

31:24 Scott Ingram: You know, these, these are the levers. You're in complete control. You just tell me what you want. You know, we all say we want choice, but we don't. And honestly, I think negotiations and so many other things, it's just so much easier because I think a lot of the fear, if you're in that other person's shoes, if you're in procurement, the worst thing that can happen is you feel like you got taken for and somebody else got a better deal than you did. Yes. Well, if everybody gets the same deal, that worry goes away.

31:51 Katie Jane Bailey: Yes. You know, not discounting, Scott, we could talk about this for hours, but not discounting is so wonderful. Like, it's kind of ironic to say because as salespeople, we're like, where's my leverage? I need to have leverage to be able to move this, move the needle forward. But if it's just so straightforward and clear and you can go into every conversation saying, this is the price, 100%, and they're like, well, we're not gonna move forward unless you give us a discount, you say, Okay, then you can't buy Figma. Yeah, you know, it's… you're exactly right. It's linear, it's clear, and it's fair.

32:27 Scott Ingram: Yeah. And that is lazy leverage.

32:30 Katie Jane Bailey: Yes. Yes.

32:31 Scott Ingram: If your go-to move is discount, boy, you need to work on your sales skills.

32:38 Katie Jane Bailey: Scott calling people out right here. I love it. I totally agree. Yeah. So, and I think that's like, I would love to know what percentage of companies don't discount. And what I see is people who are buyers are shocked because they don't know how to buy if there is no discount. Like, that is, it's not only a sales lever, but it's a buying lever. And so you talk to these people who are like, what do you mean you don't discount? Like, why am I talking to you? What's going on right now? You know, I think our head of sales, Kyle, thinks that all SaaS companies should adopt no discounting. And I totally agree.

33:14 Scott Ingram: I do too. You know, it's such a better buyer experience too.

33:17 Katie Jane Bailey: Yes. Right. Yes.

33:18 Scott Ingram: The very first car I ever bought was a Saturn. And that was Saturn's deal. Like, the price is the price. And I've bought a couple more cars like that since then. I mean, I bought a Tesla. The price of the Tesla is the price of the Tesla. I love it. Like, there's so much wasted energy and it's over not very much at the end of the day. You know what? Like, look, believe in your product, price it fairly and at a good value. And let's just do this. Like, that's such a silly thing to get wrapped around the axle over.

33:47 Katie Jane Bailey: Oh, I totally agree. Yeah, we've spent too much time talking about it already. No.

33:52 Scott Ingram: All right. All right. Moving on from the discount. This seems like a really good place to tell you about Proposify. One of the places that you can get away from discounts and really articulate the value of your solution is in your proposal. And Proposify is just the tool to help you do that. Not only can you quickly reuse elements that speak to your future clients' most important priorities, You can also know when people are looking at your proposal and how long they're spending in each of those sections. Check it out. It's really cool. top1.fm/proposify will take you straight there. And now back to my conversation with Katie Jane about her mega deal. So, so what happens after this meeting? Like, how does this meeting conclude? And, and then what happened?

34:39 Katie Jane Bailey: Yeah. So the meeting concludes and we actually, the procurement team basically says to the business team, we're walking away. And that was a risk that we had to take on. Like, we had to be like, we can't do this deal the way you guys want to do it. And so it's either walk away or you play on our basketball court. So they walk away, and the business team, the end users, the people from the trial who we are, you know, like, if you almost think of this as like what's going on on stage, what's going on backstage. On stage, I'm like meeting procurement. I'm like having these, you know, high-profile meetings in London, which is so fun. And backstage, I'm like, let's extend your trial. Let's make sure you talk to these other customers. Let's, you know, so you're, you're driving value. You're pushing the end users on how does this make a difference? Why? What's different in the last 2 months than before you were on Figma? So you're kind of like seeding this need for Figma while you see everything else getting harder and harder. Because if a team doesn't love and commit to buying Figma, we will totally lose in a legal negotiation. But if they love Figma, we will reach a conclusion. We will be able to work with a company because the buyers, the end users, are fighting for us essentially. And so, so that's kind of like what's going on backstage. So on stage, your procurement team says, this is impossible. There's no way we can do this. And the backstage the actors are like, oh yeah, this is going to happen. So we hear from them again and we find out. So with this company and I'm sure a lot of companies, you can't really start the official buying process until the team says, yes, we are moving forward with Figma. So they tell us, yep, we're moving forward with Figma. We are going into the gauntlet of security review, legal review, everything like that. So there's like kind of like 3 tracks now, right? There's security, there's legal, and there's a formal pilot that they want to set up with us. And so Another thing that's fun, a part of this story is Figma. We don't have BDRs. We don't have sales engineers yet. We don't have like support bolstering us on the sales front. You have so much support from cross-functional partners with like legal and security and things like that. But like when it comes to managing this deal and me looking at this massive ship, we're about to like try to, you know, set sail. Like it's me and Marissa, like Marissa was my partner in this deal. And so, so we get started and we're like, okay, step 1, let's get started with a security review. Security review is a 299-question review with evidence required for every single question. That's a lot.

37:24 Scott Ingram: Some nasty security reviews. That's extra nasty.

37:27 Katie Jane Bailey: So, and that was after one we had already filled out. Isn't that crazy? I was like, yeah, yeah. So I have this, I'm looking at this like massive review and it's so fun how in the weeds we can get on this, Scott. This is so fun. And keep in mind, we don't have a team that fills out reviews for us. So I now have to ask for resources internally from my security team who are actually managing security and my data privacy team and my engineering team to allocate resources away from their jobs that are actually, you know, actually building software, actually managing security, actually doing data privacy.

38:03 Scott Ingram: So the correct answer to the question is this would be really secure if I wasn't so busy answering all these stupid questions.

38:09 Katie Jane Bailey: Yeah, exactly, exactly. And one thing I had never done before this deal was sell internally to get buy-in on why we should work on this deal. And oh my gosh, this was a lesson in that 101. I remember after the first security call, I sat down on my couch and I was like, I don't know if I know how to do this. And Marissa was just an expert. Like, she is so incredible with this. And so we really teamed up to, you know, not only like sell this internally, but also to like provide support for it. You know, at one point our security team put in like 100 hours on this review. At one point we sent our head of security an anxiety coloring book because we were like, we know how stressful this is. So that's going on and it's just like crazy. I'm sure you hear all the crazy security review stories. Like, what are your thoughts on that?

39:05 Scott Ingram: Well, I don't to talk about it anymore because it's… I'm going to need a coloring book myself.

39:11 Katie Jane Bailey: Yeah. Yeah.

39:11 Scott Ingram: But I want to kind of put this in perspective of the rest of your world because this isn't the only thing you're doing. So how are you managing how much time you're spending on this particular opportunity and balancing it with… I'm sure you've got other deals that you're working.

39:29 Katie Jane Bailey: Yeah. I don't know. I mean, I think with Figma, yeah, you're exactly right. Like we close on average like 15 to 20 net new deals a quarter kind of thing on the enterprise team. And then we have some upsells. And so this is one of, 'cause if this is, let's say, you know, I worked on this for 4 quarters, so one of 60 deals and, you know, 75% of my time. So, you know, you just do it. I don't know. You just, you just keep grinding. You keep like, you just put in the time. I think one thing about it is like, that this deal was so fun. Like it was such high risk. It was so like, we, we are pioneering, you know, like after every call, Morris and I would have a recap and like, okay, here's our next move, you know? And, and so that really energizes you as a salesperson to keep moving forward, even though there were times that you're like, I'm pulling all of my hair out. And so I think it energizes you to do the other work as well, because you still gotta do the other work. You still gotta hit quota. You still, you know, you still gotta do all these things. So honestly, I don't know, except that we just did it.

40:35 Scott Ingram: Yeah. And how were you managing kind of the risk side of things? Right. Because you have to kind of consciously decide, okay, I'm going to put a ton of energy, a ton of my time into this opportunity. And there's obviously, if we win, it's huge, but we could just as easily lose this.

40:52 Katie Jane Bailey: Yeah. So this is maybe counterintuitive, but I just told people that all the time. I would be like, you know what? There is no guarantee this is gonna close. There is no guarantee that we're gonna make it through, but I'm pretty sure we can. And with all the right people in place, we have like, this is ours to lose and we just gotta keep moving forward. And like, when I think about this deal over a, you know, 9-month period of kind of like a lot of action in my head, I see like all these people just running in crazy circles all around me and me just like confidently looking like taking steps forward, like we are going to get this deal. And I think it was like, you know, that's what makes it fun. That's a, that kind of like, you know, and so, and I think everybody loves high risk, high reward. You get people excited about it. You're like, oh my gosh, legal, this could be our biggest deal ever. You know? And like, I don't know, you just, you rally the troops, you, you get people going and you bring 'em onto your team. And then, you know, this was, this was a huge team effort and you help people feel that way. So, we all knew the risk going into it and the risk gets crazy towards the end, so that makes it fun.

42:03 Scott Ingram: Yeah, yeah. Well, and it sounds like you did a great job of managing that because it's one thing to just go blindly and, you know, be overly optimistic about this while other… especially in other roles in the organization that tend to be a little bit, I don't know, more realist and pragmatic than us in sales, you know, with our happy ears and happy eyes tend to be. I think having some of that recognition of, look, I get it. Like, there's totally a risk that this couldn't happen. I think that builds a lot of trust in, in what you're doing and not, okay, here, here we are blindly following Katie Jane and, uh, we're probably going over the cliff on this one. This isn't gonna be fun.

42:41 Katie Jane Bailey: Yeah, totally. Totally. Yeah. I also, you know, because this was so cross-functional and this was a huge lesson for me was we met our cross-functional partners where they were. So, if there was any ounce of work we could do in the deal, we did it so that that it was like, this is very much a shared load. And that was a huge lesson for me as well. But yeah, just like, you know, we're selling it, we're co-selling as a team here.

43:05 Scott Ingram: Wait, I, I missed that. So what was the lesson there?

43:07 Katie Jane Bailey: So the lesson is I cannot expect… so my security team have very different KPIs, or my legal team, very different success metrics. You know, their goal is to slow down a deal. My goal is to speed up a deal. And so it's like conflicting even, you know, and So I cannot expect that they are going to help me in this deal if I am not like with them in this, you know, like if I send, send it over the fence and I'm like, hey team, please review this 60-page MSA and get it back to me in one week. Like there's no way that happens, you know? But, but if you're like, hey, we are increasing deal size, we are pushing them on this, we're telling them no on this, here's how I'm handling the backside of this, like from a legal perspective, then they, you know, we're working really hard to make sure that this is very much a team effort. It's not just us adding to their workload. And that's the lesson is in that cross-functional partnership, you can't just expect people to kind of deliver for you. It has to be something that you're working together. Does that answer the question?

44:13 Scott Ingram: Yeah, it makes a ton of sense and it aligns really well with an epiphany that I had last year playing The Sales Game. Shout out to my friends at The Sales Game. And I came out of that after playing a 12-hour round overnight because I played the first virtual experience around The Sales Game with a bunch of Australians. So the game started at, I don't know, 6 PM on a Friday. And I played until oh dark 30 Saturday morning, but I came away from that with the understanding that sales is leadership. And that's what you're doing here, right? You, you are leading a team. You don't need to have a title to be a sales leader. And when it comes to this type of thing, you're leading your team and you're leading your client's team. And you have to be a great leader. And a great leader doesn't just like, to your point, chuck stuff over the wall and say, here, make this happen. I'm gonna go play golf.

45:08 Katie Jane Bailey: Mm-hmm. Yeah, exactly. Yeah. I'm gonna go work on other deals, you know? Yeah, totally.

45:12 Scott Ingram: Yeah. All right, let's keep going.

45:15 Katie Jane Bailey: Keep going. Yeah. So, okay. All right, we're almost to the good part. Well, at least my favorite part. Okay. So you have step 1, which is the security review. You have the pilot and the pilot is basically like, you know, we'll give you access, blah, blah, blah, all this stuff. And so my goal with the pilot was, hey, this is, you know, free access for you guys. Let's start onboarding. Like, let's start moving forward. And so we start seeing people coming into the platform every week and the usage is starting to grow significantly. Like we're talking like increasing over 100% every week and I'm just like feeding it like, yep, here we go. More people, more trainings. Let's, let's do this. And you know, the customer gets a ton of value outta that cuz they get like a running head start. And I'm like, yeah, we're like, we're fully transparent. We're transparent on the end date. We're transparent that if the contract is not signed by the end of this trial, we know what's coming. And, and it, it was a huge priority for me. To be transparent with every single person who worked on this deal. Procurement, the month, the final month of the trial, got an email every Monday saying there are 25 days left in this trial, 25 business days. There are 14 business days. Like, it was like constant reminder. And so the pilot starts, there are 3 trains leaving the station. Security, train number 2 is the pilots, number 3 is the legal review. So the, remember, this is a very highly regulated company, and so the legal review this mess of like, how do we navigate these things? And it's kind of this, you know, they're playing, well, we can't do that because of regulation. We can't do that because of regulation. And we're just trying to kind of navigate and how do we actually work together? How do we negotiate? And at one point during the legal review, our procurement person is a little bit flustered and says, come on, Figma. It's time to play with the big boys. And we were like, sorry, what? And it just lit a fire under our legal team. We were like, how do we even respond to that? Do they… what do they know? What do we do with that kind of phrase? Like, we have to win this now. And it was like this driving force of like, all right, here we go, team. And like, I swear I'll be 85 talking about Uh, it's time to play with the big boys.

47:33 Scott Ingram: What did they, what did they mean by that?

47:35 Katie Jane Bailey: They basically meant that they were trying to say, so Figma's really small, remember? So they're basically trying to say that what we are offering is not like competitive with these very large company contracts, right? Like there's no way you can actually continue fighting for that. You're playing with the big boys now. Like that's not something you get to fight for. And Figma, our legal team, they're fierce with their, with what they will agree to, what they will not agree to. And most, I mean, if you're a small SaaS company and you have one of the largest companies in the world wanting to buy your software, you usually just like, whatever you say, let's just get this done. We just want, if we can call you a customer, we're down, you know? And Figma is like, we would love for you to be our customer and here's how we can do it. It's a lot, you know? Yeah. So it was this really weird, like, it was an intimidation factor, you know?

48:31 Scott Ingram: Yeah. Yeah. Well, and they're, they're sort of the playing the game, you know, I will, I'll put this in context a little bit too, because, you know, it's easy to look at this and go, oh my God, like I'm just in sales. I'm just trying to get this freaking deal done. Why don't we just agree to everything? What, you know, what's, what's the deal? But if you look at, and I talked to a lot of people about, you've got to take this more holistic view. You got to think about like the total value to the organization. In some future, maybe Figma will be acquired. And having been at companies that have been acquired before, I will tell you, if you have a really great legal process and you hold the line and you do a good job of this, your value when, when big giant company comes in to do their due diligence and starts to look at the contract, If you bent over backwards and did whatever, what every big company wants you to do, your contracts are a giant mess. But if you do it right, you know, it's your valuation is higher. It's an easier deal to get approved and to get done. So anyway, just random context for people, but I've, I've seen the other side of this and it does, it does actually matter. Yeah.

49:46 Katie Jane Bailey: Well, you know, and I think that's one thing that as salespeople, you know, we want to get the deal done at all costs. And I think that sometimes the way I like to think about it is we are the front line of protecting our company. You know, like we are the people who protect Figma from this crazy legal negotiation. We're the ones who protect the resources from, you know, you have a limited number of resources. You have to be wise with them. And so I think if, if you can, like, as a rep adopt that mentality, it, it totally changes the way you sell your product. At least it did for me. Yeah. So I totally agree.

50:25 Scott Ingram: Yeah. So, so now you're playing with the, with the big boys now.

50:27 Katie Jane Bailey: Yep.

50:27 Scott Ingram: We're here. It's getting really fired up now. Now it's on, right?

50:30 Katie Jane Bailey: Yes. Yes. Yes. Okay. So this is the fun part. So it's been a 1 year, hundreds of hours put into this deal. It's now our largest deal we've ever closed. Well, it's the largest deal that is still open, not closed yet. We get to the final 2 weeks. Okay. We now have 1,200 people on a trial. Active daily, like in it. And there are 3 points that Figma has not given on yet. And I told them from the very beginning, just so you know, one of those is we don't discount and you're gonna face that this whole time because, you know, I don't wanna get to the very end and my procurement guy be like, I wish you would've told me you didn't discount. You know, something like that. Like I wanna be super transparent from the beginning. So we had the final call. And it is C-level and 3 executive directors and heavy hitters and myself and my CEO Dylan, who is incredible and such like, yeah, Dylan is amazing. I'll tell you more about that in just a second. So we have this call and Dylan and I are prepping for it and we're like, all right, all we gotta do is just tell 'em no. And that this is, this is what it is. And so it's 30 minutes and And it was crazy. It was like so much frustration of this small company that, you know, small, I mean, 280 is not tiny, but it's comparative to who we were talking to. It's this like speck, right? And we're telling them no. And we're saying we understand the risk of saying no, but we have to do what is best for our company and we are not willing to sacrifice price our company for this contract. And it was so crazy. Like, it was so fun. It was like one of those calls where time is slowed down. Like, I'm just, I'm totally playing that role, you know? And we're just like, I can't believe we're having this conversation right now. So the call ends and part of it was they wanted us to extend the trial, but it was quarter end and we were like, nope, you sign this deal now or you lose access. And they did not want to lose access. And we walk away and we're like, okay, we're gonna go back to the drawing table. We're gonna reconvene and we're gonna figure out a path forward. So Dylan says, and so one of my favorite things about Dylan, our CEO, is that he just has this incredible trust in our team. He's like, Katie Jane, what's the best path forward? Kelly, what's the best path forward? So he says, all right, I need to know every aspect of this deal. So we're like scrambling, we're like putting together all the details and we're like laying it out into this brief, you know? And we take Dylan through the whole brief and And at the end of the brief, Dylan looks at us and says, okay, we might have to walk away. And we were like, what? Oh my gosh, a year, hundreds of hours, like, are we seriously going to walk away from this? But, you know, I can't really argue with that. And so, we all say, okay, here's… let's put together our final offer and send it over the fence and see what happens. So meanwhile, we get a few emails from our board and a customer has reached out to several members to understand what's going on. So we, we have pressure from like all sides on this deal. Like, I like to say that I'm not afraid to introduce friction and this was like the ultimate like friction situation. And so I'm like having the time of my life, you know, and we put together this offer. And we send it and it's like 5:00 PM California time and we all close our computers for the night. And my legal team's like, yeah, 33% chance this closes. And we wake up the next morning and I check my email and I have an email from procurement and all the email says is, we've accepted your terms, please process for signature.

54:21 Scott Ingram: Oh, so how did you feel reading that email?

54:24 Katie Jane Bailey: Like it was Christmas morning. I mean, it was. So it was so exhilarating. It was so fun. And then to be able to go back to the team and be like, we did it. Like, we all did it together. And like, this is the biggest deal. Like, it was just, oh, it was so fun.

54:43 Scott Ingram: So you went back to the team. So this is, this is COVID time though.

54:48 Katie Jane Bailey: Yes, this is COVID time.

54:50 Scott Ingram: So you're, you're doing all of this virtually. There's no, we're in the same conference room, we're like war rooming this thing. We're now, we're high-fiving and, and, you know, popping champagne and everything. This is still, here I am sitting all by myself in, in my office managing through all of this. Is, am I getting this right?

55:10 Katie Jane Bailey: Yeah. I mean, my, the head of sales, Kyle, who is so great and he was really crucial in all of this too. He was like, I mean, he said it perfectly. He's like, man, I'm like cheering and clapping and then I'm picking up food off the floor for my toddler. And I was like, yep, that is this deal. So yeah, it was COVID. It was, it was crazy.

55:32 Scott Ingram: Oh my gosh. Oh my gosh.

55:34 Katie Jane Bailey: I know.

55:35 Scott Ingram: What a great story.

55:36 Katie Jane Bailey: Ah, thanks. It's so fun. Thank you for letting me go into the weeds. I was like, how do we tell this story in just a few minutes? You know?

55:43 Scott Ingram: Yeah. That's not a thing.

55:44 Katie Jane Bailey: Yeah.

55:45 Scott Ingram: Yeah. How do you, how do you talk through, yeah, how do you talk through 2020 in, in 10 minutes? Right. It's that kind of thing. It's like, no, it's gonna take a minute to unpack this.

55:53 Katie Jane Bailey: Yes. Yes.

55:54 Scott Ingram: That's fantastic. Any other kind of big learnings or insights or things that, that you took away from that deal that are going to inform kind of future big deal efforts that we didn't kind of talk about going through the story?

56:09 Katie Jane Bailey: Yeah, totally. I think, you know, as an early enterprise product, there are more unknowns than knowns when we are selling. And this deal helped us uncover so many things that wouldn't have uncovered for a couple of years or, you know, a year or 2 at least. And, you know, Figma has never been through a security review of such rigor. And we now know how to do it. We know, we know what value needs to go in first. We know, you know, we know how to drive value before you start any of that, any of that. And it kind of illuminated as a company, not all the way from like me, all the way up to Dylan, our CEO, of here's what it takes for us to close these kinds of deals. And that is huge for an early sales team and an early enterprise team.

57:03 Scott Ingram: Yeah, that's, that's fantastic. You know, I think one of the other things that I was going to bring up earlier, but I didn't because I thought it might come up again. And I feel like this probably did happen as you were going through. If you do a great job of selling to the business while you're doing all this work with procurement and they're trying to beat the living snot out of you. Like they're, they're in their role, right? That, that's their job is, is to, you know, do make your life hell.

57:30 Katie Jane Bailey: Yes.

57:30 Scott Ingram: And the business in almost all cases trumps procurement. So you were experiencing all this friction, right? Because you were under pressure from all sides. But, you know, if you do it right, you can create that same type of pressure for them to where the business is saying, we have to get this deal done. And I think you did that when you, when you held the line on Sorry, we can't extend this pilot because exactly, probably put a ton of pressure on them because now they've got a thousand people saying, "Uh, yeah, you can't turn this off," or exactly, exactly.

58:10 Katie Jane Bailey: And like, I mean, introducing friction, right? Like if you as a rep, if you don't have the courage to kind of introduce that kind of friction, then who knows how long that sales cycle would have gone on. You know, who knows how many more resources it would have taken from Figma to close that kind of deal. But instead our whole team was like, nope, we are ready to introduce that kind of friction. And that's what ultimately got it over the line.

58:34 Scott Ingram: Yeah. Brilliant. Absolutely brilliant. I'm so glad we got a chance to do that. And now I'm looking at my regular list of questions going, oh my gosh, we have like a whole interview to do. This is so much, this is so much fun, but now, you know, hopefully Actually, folks may want to break this in 2. You know, there was the first hour.

58:51 Katie Jane Bailey: I know. Yeah, yeah.

58:52 Scott Ingram: Now we get, now we get to dig into Katie Jane and, and how she manages the entire rest of her life and, and all the things that you do to make this work, starting with kind of my favorite area, which is just getting into the weeds of how are you managing your day-to-day. And I know you listen to the show, so I always set this up in terms of alarm goes off, tell me what time that happened.

59:18 Katie Jane Bailey: Yep.

59:19 Scott Ingram: And I want blow-by-blow.

59:20 Katie Jane Bailey: So alarm goes off at 6:30. I am… wish I could say I pop right out of bed at 6:30, but more like 7. I'd like to go for a walk or do some Pilates in the morning just to separate my wake-up from my computer, since especially right now there's very little of that. I'm also big on setting my coffee the night before, so in the morning I just to press on, big part of my morning. And then I'm usually online around 8 or 8:30. So I'm really big and, well, actually our, our whole team is really big on time blocking. And I know a lot of people who you talk to are also big on time blocking. And so I do 8 to about 10:30, I'm on customer-facing calls. It is important to note that we, I think I mentioned this earlier, but we don't have any SDRs or BDRs, so we're full-cycle reps at Figma. So my calendar availability is only open from 8:30 to 10:30. So calls, 8:30 to 10:30. Then there's usually some kind of internal meeting in that 10 o'clock hour, 10 to 10:30 o'clock hour. I then do a kind of like a brain hack where unless an email is extremely urgent, I ignore my inbox until 3 or 4 PM and I just outbound. I go, I respond to any emails that have come from my prospecting. But I'm, I'm really trying to, a guy on my team recently discovered the term like golden hours, right? Those are the hours that you're like at peak performance and you only have so many of those a day. And so I like to get in an hour and a half to 2 hours of prospecting in that window. And then I have, I get to my inbox around 3:30 or 4. For me, because I am, I mean, I think everybody's probably like this, I know I will get to my inbox. I cannot go to sleep unless I am close to inbox zero. So, if I trick myself into doing inbox later, I will definitely get to it. If I wait to do prospecting until the 3 or 4 o'clock hour, I will get very little done. So, that's, that's my normal day. And then I cook dinner with my husband and we go on a long walk and especially during COVID and watch some shows. That's, that's my day.

1:01:35 Scott Ingram: Nice. I want to hear more about this brain. How are you… you're actively ignoring email the better part of the day. How are you doing that? I'm an inbox zero guy, but I don't get away from my email as much as I would like to.

1:01:50 Katie Jane Bailey: Yeah, no, it's, it's hard. I mean, there's some… there's like even like an endorphin hit when you're like, oh, I got an email, you know? So, I mean, if I get an email from one of my top customers or top prospects, Like that gets my attention, of course. But for the most part, even active deals. So my system specifically is if it's like unopened, then it draws my attention. But if it's opened, then somehow I'm able to like ignore it a little bit better. So I just open the emails, I scan 'em, I check out what's going on, but then I say, I will get to you later. And it is hard. Like it is not easy, but it makes such a big difference. And then when you start to see that the difference of prospecting later in the day versus earlier in the day, your brain kind of is like, I get it. Yeah, this is the right thing to do. And yeah, and that's kind of how I trick myself into doing it, I guess.

1:02:39 Scott Ingram: That's really interesting. So I think I sort of get it. It's not like you are not opening your inbox. It's not this giant mystery of, oh, it'll be so interesting at 3:30 to see what has actually come in today. You are quickly making sure that there's not something on fire, but in almost all cases just saying, great, nothing I need to do right now. I will deal with you at the end of the day.

1:03:05 Katie Jane Bailey: Yep, exactly. Yeah, actually, question for you with your customers or prospects, what is your like minimum? You will at least hear from me in 24 hours, 48 hours. Like how quickly do you hold yourself to get back to people?

1:03:20 Scott Ingram: That's a good question. It's not an expectation that I typically set directly with my clients, but I mean, my own rule and just my own system. Um, if you don't hear from me by the following morning, which is when I'm doing my heaviest kind of email dealing, then, then something's wrong. And, and if it's… if that's not going to happen, I will have set an out-of-office message to set the expectation differently. And I, I think, you know, one of the things that's pretty interesting about sending several thousand emails every week like I do to all of you on the listener list, especially over the holidays, use is I get lots of out-of-office messages, and I think there's such a missed opportunity in that. They all look almost the same. They're so standardized and so boring, and I think there's such an opportunity to not only do more when you're actually out, but to also use it in other creative ways, even if you're using it like the way you're talking about from a golden hour Like, even if you say, hey, you know, I typically will dive into my, my email around 3 or 4 o'clock. So you should, you should expect to hear from me by the end of the day. If you don't need a response, let me know. Something like that. I think.

1:04:39 Katie Jane Bailey: Yeah.

1:04:40 Scott Ingram: And you could just have more fun with it too, you know? Yeah. Gosh, there are all these out-of-office emails, having seen hundreds, especially over the holidays. They're boring. I was, you know, I send this newsletter and then, you know, in come these waves of email.

1:04:57 Katie Jane Bailey: Yeah.

1:04:58 Scott Ingram: And not a one is entertaining or different. And to me, that's a missed opportunity.

1:05:03 Katie Jane Bailey: Yeah, surprise. I mean, like, you get some really fun, interesting, colorful people in sales, you know? Like, you'd think we'd be better than that, right?

1:05:11 Scott Ingram: Exactly.

1:05:12 Katie Jane Bailey: Huh. Yeah. Okay, now I'm inspired. My out of office will never be boring again. There you go. There you go.

1:05:17 Scott Ingram: I'm gonna email you all the time now to see what it is.

1:05:20 Katie Jane Bailey: Yeah, yeah, yeah, totally.

1:05:23 Scott Ingram: Me all the time.

1:05:25 Katie Jane Bailey: Oh man. Yeah, yeah. I think that like the reason I ask that of like, how do you think about that for your own setting your own boundaries, is I think that it's really easy to let your inbox like the tail wagging the dog, right? Like your inbox can drive your whole day if you're not careful.

1:05:41 Scott Ingram: Totally, 100%. And it's, it's one of those things again, like I wish I was better at that. I'm, I'm good at a lot of things in my productivity process this, but that one, that's, that's not one actually.

1:05:52 Katie Jane Bailey: Nice. Sounds like a 2021 goal.

1:05:53 Scott Ingram: Maybe, maybe I, I may, I may be inspired to kind of play with that and, and see where that goes. Are there any other kind of core habits and, and routines that you have that are core to the way that you function?

1:06:08 Katie Jane Bailey: Yeah, so I would say that, so it's like, I don't know exactly how to answer this, but when I latch on to something that I find makes a difference in my day-to-day. So like, for example, I'm literally staring at SPIN Selling right now. SPIN Selling, I've read it a couple times. I just think it's so great as a salesperson. I really love it. And so when I find something like that, which is, it's a book, it's not just an article, it's not just something that's kind of like easy to dispose of. It's not something I do every single day, but I would say that like once a week, every other week, I'm opening up whatever that source material is, and I'm like revisiting what need-payoff question examples, you know, or something like that. And it goes back to like that lifelong learner aspect. This is so cheesy, but the first time I ever learned about MEDDIC, I was like, this is amazing. I love this. I can't wait to apply this, you know? And so MEDDIC is like everywhere. And so I'm someone who kind of surrounds myself with Like I may not do engage in this every single day, but I I put these things in my view where I'm looking at it. You know, so spin selling is one. Another one is I have a sticky note on my wall inspired by Marissa that says world class sales team, and that is something that I want to be a part of. I want to be part of building. I want to contribute to it. And the exercise of thinking of thinking what is a world class sales team? What does it take to be a world class sales team? And stepping on the scale. And being like, where do we really need to improve? How do we, how do we think about this? Those are other things that I would say shape me as an individual so that I'm constantly evolving. And then I guess this is a really big one, but I'm a huge goals person. I set 10 goals every year and I have done that for 10 years now and I track them throughout the year. They could be any, anywhere, anything from like like, you know, get a wardrobe stylist or something, to all the way to like personal finance goals and things like that. And like this year, one of them is last year I created a work vision statement for myself. So what is it that I'm working towards? And this year my goal is implement that work vision statement. What does that actually mean to implement a work vision statement? So I would say that like those are not day-to-day things, but they, they definitely shaped me as an individual.

1:08:36 Scott Ingram: Fascinating. So again, many, many, many questions. Let's start with the goals thing. How many of those 10 did you accomplish in 2020?

1:08:47 Katie Jane Bailey: So I would say on average I accomplished like 7 or 8 of them. My cousin and I do it every year together, and every year we spend 1 hour reviewing what we accomplished and 1 hour setting goals. So yeah, I would say about 7 or 8 every year.

1:09:02 Scott Ingram: And how often do you review those throughout the year?

1:09:05 Katie Jane Bailey: I think we were, well, could review them more often, but the thing is that we, I set goals that are top of mind of what I am interested in anyway. And so they're kind of always there. It's like, like for example, I was listening to Brené Brown, Jim Collins podcast recently, which was so fun, highly recommend. And, you know, they're talking about this like chaos, right? Like navigating chaos. And my vision statement, in case you're interested, is bringing structure out of chaos. And I, I think that that's what we do as salespeople actually. And I think that you can like build on that in so many ways. And so like, it's something that I, I invest time into because it's a goal, but then it's also just kind of like top of mind. So actively reviewing, if I'm sitting down and saying, where am I at? Probably like 3 or 4, maybe a little more like 4 to 7 times a year. But like my husband and I, we, we talk about them. Like what last year, one of my goals was, this is like embarrassing to admit, but learn American history. Like there's so much history that I actually didn't really pay attention to in high school. And I'm like, I wanna learn all these things. I wanna know who these names are. You know, you know the basics, but you know, and so every, like even just looking for a Netflix show Oh, this is some of our American history. Let's watch this. This is part of my goal. So yeah, it's kind of a weird answer, but that's how I think about it.

1:10:28 Scott Ingram: That's awesome. And you answered my, my next question about the vision piece. I really am interested in what are your conclusions? What are the things that you're thinking about when you think about what a world-class sales team is?

1:10:42 Katie Jane Bailey: Hmm. Yes. Well, okay. I will only answer this question if you promise to answer as well.

1:10:48 Scott Ingram: Ooh. All right.

1:10:50 Katie Jane Bailey: All right. So, okay, so super fun. Marissa just had our whole team actually do a mind map around this concept. So everybody had to do this exercise and you, world-class sales team is in the middle. So for me, I think that if we can be a world-class sales team, then we have to operate like a team. We have to celebrate each other's wins, grieve each other's losses. Give peer feedback, see feedback as a strength. You know, like, what does it look like on us in a sales org to work as a team rather than a collection of individuals with goals? So, that's one big one for me. Then, for me, it was, you know, pretty basic numbers like 100% of the team hitting quota or exceeding, close rate of, you know, pick a number and higher. I think that creating, like an internal and an external brand as a team is really powerful. So, you know, what is our relationship like with legal? What's our relationship like with security and product? Are we, are we giving feedback to the product? And then externally, you know, are we, you know, how do our customers talk about us? How do our peers talk about us? How do we engage with community as like our team, you know? So those are kind of my big pillars and the one that's missing there that is like terrible to say, but, and I guess for me, I kind of take it for granted is like, where's the customer experience in there? Right? So I personally think that if you're, if you are working on your sales hygiene is what I call it. So, you know, all the basic things, you are hiring caring, interesting, curious, creative people, then naturally we're all like working towards a fair, good buying process. And that's ultimately what creates a good experience for the customer that I, I could probably put that a little higher on my mind. Map.

1:12:42 Scott Ingram: Oh, good, good stuff. Before I share my answer on what it means to be a world-class sales team, especially if you're interested in this topic, you should know about Terryberry. Terryberry is all about building great performance-based cultures through recognition programs. Top-performing organizations all over the world have turned to Terryberry and their award-winning 360 recognition platform platform to reward contributions towards success. If that's the type of culture you're looking to build, check out Terryberry. top1.fm/terryberry will take you straight there. And with that, here are my thoughts on world-class sales teams. Okay, so I've cheated a little bit and I've pulled up a note that I have in Evernote that I've been working on because I'm, I'm building towards a thing. I'm not going to put any more definition around it. Yet.

1:13:37 Katie Jane Bailey: Okay.

1:13:38 Scott Ingram: But I'm building towards a thing that I'm calling Fundamentals of Sales Success.

1:13:43 Katie Jane Bailey: Ooh, okay.

1:13:44 Scott Ingram: And because it feels like if we look at the whole of the sales world and the content and the stuff that's out there, there's a lot of really kind of tactical process type of stuff. But I really feel like, again, having had over 100 of these types of conversations.

1:14:05 Katie Jane Bailey: Yeah.

1:14:06 Scott Ingram: There's a layer that is fundamental and kind of more foundational before you have to worry about the, well, what do I say and what is my subject line and how do I negotiate and just all of those things. There's some more core pieces that are around mindset and mental health and around productivity and around your process and around kind of your goals and your habits. And so the work that I've been doing is really geared more towards the individual, although interestingly, there's a whole component around team selling and relationships. And I think you called it out really well in that there is… we call it, or we call ourselves a sales team. We don't act like a team. You know, we, at best… well, not at best, I think typically we are a collection of individuals.

1:15:08 Katie Jane Bailey: Yep.

1:15:09 Scott Ingram: But very rarely is there this kind of collective, hey, together we're gonna make this happen. We're working to help each other get better and to grow and to win more and all of those those things, right? So I think the very first piece is if you're going to be a world-class sales team, step one is you have to actually be a team.

1:15:35 Katie Jane Bailey: A team, exactly. I totally agree. Yeah.

1:15:38 Scott Ingram: And how great is that, right? I think, you know, we need to dispel this myth that is kind of the lone wolf in sales because, A, it doesn't work. It's not really a thing.

1:15:49 Katie Jane Bailey: Yeah.

1:15:50 Scott Ingram: And we need each other, and it's so much more fun.

1:15:53 Katie Jane Bailey: Oh yeah.

1:15:54 Scott Ingram: If we can truly create that type of team environment. So, I think that's the first thing. I think you kind of touched on another piece. I've been, I would set this up as just, I don't know, like do the right thing. It's customer experience. It's all these things. We launched a website, well, it's just a landing page, the beginning of this year that is salesuccesseverything.com. And I love this term so much because one, there's the most obvious level of sales success everything because It's just, you can link to all the stuff that we do. There's podcasts, and there's a summit, and there's books, and there's just so much stuff that we are doing. But bigger than that, I see Sales Success Everything as a mindset and as a verb.

1:16:44 Katie Jane Bailey: Ah, interesting.

1:16:44 Scott Ingram: So, if you embody all of these things that are what I believe is a great sales professional, and if you've listened to enough of these interviews, and you've heard enough Katie Janes, you realize like, damn, these aren't just great sales professionals. They're great. Not just… they're great humans.

1:17:02 Katie Jane Bailey: They're great people. I told… yes, 1,000%. Yes.

1:17:06 Scott Ingram: So sales success, everything is embodying that.

1:17:11 Katie Jane Bailey: I see what you're saying.

1:17:12 Scott Ingram: Everything with that degree of excellence and just humanity and servant leadership and all of that stuff.

1:17:21 Katie Jane Bailey: Yes, definitely. Well, and I think that we're in this really fun transition of sales as like sales is changing. Like the role that we play is, is different than it was 10, 15 years ago, you know, like for Figma, everything I tell people is pretty much online. They can look at it, you know? So I'm no longer like a barrier to entry for even using my product. Like we have a free product. And so what is my value as a salesperson? Person at Figma to my customers. And, you know, I think you're exactly right that like, it's everything. Like my, how I talk to people, how I work cross-functionally, how I interact, like, and that, that's all driven from, you know, how do you attack not only like your job, but life in general?

1:18:07 Scott Ingram: Yeah. Yeah. And the last thing I would add is it's kind of this development and growth focus. It's, we're never done getting better. You know, there's, there's always better. And that to me is just, is so compelling and so interesting and, and such a pull, right? Like, that draws me. That, I mean, that's, that's why I can talk to folks like you for hours on end.

1:18:33 Katie Jane Bailey: Yeah.

1:18:34 Scott Ingram: And, and it never gets old. Like, this fascinates me, and there's always something that I learn. There's always something that I take away and something I'm going to try So cool. And kind of play with and, and do that kind of, that kind of thing, right?

1:18:47 Katie Jane Bailey: Yeah, totally. And you know, it's like sometimes it takes a lot of energy to like learn something, right? And, but then when you, like, I took this public speaking course last year and I was so energized by it and it was like, I gotta take more classes. Like, this is so fun, you know? And so I, I, you can always be better. You are. Yes. 1,000%. Yeah.

1:19:07 Scott Ingram: So you just said you basically surround yourself yourself with your content and, and the stuff that you're actively learning about. Talk, talk a little bit more about what is your information diet look like?

1:19:23 Katie Jane Bailey: Yeah, yeah, definitely. Okay, so there's like day-to-day information, right? News. So like, I don't know if this is a good thing or a bad thing, but I actually use LinkedIn for a lot of just news, what's happening in terms of like the industry and things like that. Figma, our sales team and our product team, we do a lot of sharing of this article is important. This is great. This is a good read. So my like browser is like so many tabs of articles that I have ready to read. They may not actually get read until Friday, but they're all there ready to go. And then you have your like bigger learnings. So your books, your podcasts. I'm a big podcast person. I love to just walk and listen to podcasts. And so, and what I really love about podcasts too, and I think you do a really, really good job job, like fun jobs, kind of a weird way to describe it, but I really enjoy these longer, deeper conversations. That's not just like, oh, here are kind of the 3 top things that blah, blah, blah, you know, but actually getting into it. So podcasts. And then I really, I'm always reading a novel and like, I don't know, a self-help book or like, you know, some kind of like SPIN Selling or another one I just got was Secrets of Question-Based Selling, you know, something that's like pushing me to expand my knowledge. So I would say those are my 3 information diet sources.

1:20:46 Scott Ingram: Love it, love it. Obviously I'm aligned with the deep dive stuff and yeah, I can guarantee you everybody listening to this right now still does that too.

1:20:58 Katie Jane Bailey: I love it. I know, right?

1:20:59 Scott Ingram: They dropped off like an hour ago, right?

1:21:01 Katie Jane Bailey: Yeah, yeah, totally.

1:21:03 Scott Ingram: So In each of those categories, right? So when we think about book, novel, podcast, what was the most impactful one of each of those for you in say the last year?

1:21:18 Katie Jane Bailey: Hmm. Okay. Let's see. I'm going to start with podcast. So there's a podcast. It's, I think it's called Go-To-Market Grit. I'm like referencing Marissa for all these things, but she's just this wealth of like information. And just also so curious and learner. And so, she introduced our team to this podcast and it's the Kleiner Perkins podcast. And basically, yeah, basically these, a partner from Kleiner Perkins interviews these kind of like business leaders who are actually leading go-to-market teams. And they're really interesting conversations. I think I reference them like every single week in conversation. I would say that the biggest ones that influenced me in the last year was with Dan Shapiro, who is the chief business officer for LinkedIn. Oh my gosh, I just devoured this podcast. It was so interesting. I think that was the first place I heard the phrase world-class sales team. So clearly that influenced me. And he also talked about like, what is the role of a salesperson now? He, he had a really interesting career around like going from Um, studying, I think, math at Johns Hopkins to Bain to business school to LinkedIn to having some failed startups, like just all these crazy, you know, career trajectories. And then after building this massive sales team of, of an incredible product at LinkedIn, goes back to being an entry-level product manager to get product experience. And so, so much of what he talked about really resonated with me. He talked about, and actually this might be relevant to your sales success, everything, but talked about the concept between a victim state or a player state. So victim state is I never get inbounds anymore. Player state is, dang, look at how great this outbound messaging is. You know, so I think victim state and player state really resonate on a sales team, and that's something you can control, you know, so if someone out there is like, what can I do to… if, if being a good salesperson is being a good person, what can I control to change? You know, it's like, well, think about your state of mind. Are you a victim or a player? So yeah, clearly I could talk about that for a long time, but that is one influenced me.

1:23:33 Scott Ingram: Wow. Now that was just one episode.

1:23:36 Katie Jane Bailey: Yes, that was one episode.

1:23:38 Scott Ingram: Oh, that was… okay, well, I'm eager. So Kevin's gonna work his magic and he's gonna pull all these links together, and I get to see them before everybody else. So I will listen to that before everybody else hears this. I'm looking forward that one.

1:23:50 Katie Jane Bailey: Nice, nice. Cool. Okay, now an article that really influenced me or something from like a, oh man, that's a hard one. Oh, I know what it was. This guy who's a designer from Airbnb basically wrote this article about Figma completely. Like Figma didn't ask him to do it. It was completely on his own. And it was kind of this assessment of like the Figma magic and the opportunity that we have ahead of us. And it changed changed my perspective. I think, you know, Figma is an incredible place to work and we have an incredible product, and sometimes it's easy to forget that because you're in the day-to-day challenges of sales. And it was this article that totally pulled me out of that mentality. And, and now I have this new, like, oh man, this, this is a big opportunity that we have and we gotta go, we gotta be ultimate player state. So yeah, so that's an… that's the Nicole, any thoughts, questions?

1:24:45 Scott Ingram: The thought there, I love that you keep turning this back on me. The thought that I have, one of the things I think again is, is one of these kind of fundamental things is belief. And I talk about belief in terms of you have to believe in yourself. You have to believe in your product and you have to believe in your process. And the belief in your product, man, when you can get just those customer stories and when you get to to just see and hear and feel firsthand the impact that you're making. Yes, selling so much easier.

1:25:19 Katie Jane Bailey: 1,000%. Like, it's almost like, how do I get to sell something like this? It's so fun, you know?

1:25:25 Scott Ingram: Yeah. And in my world, I mean, with this, with this podcast, it's the people who reach out who are like, Scott, I've never emailed you before, but like, this has changed the trajectory of my career.

1:25:36 Katie Jane Bailey: Wow, I believe it. I mean, no one else talks about this kind of stuff, you know?

1:25:40 Scott Ingram: Yeah. In fact, I think the next episode… so I have the conversation, as you and I are having this conversation, the interview is 2 days from now, but there will be a 2-week delay before I'm able to release the interview. So sneak preview, thank you for continuing to listen. I'll be talking with a gentleman who I spoke with in 2018, and he was just in like this really rough between spot and, you know, was kind of stuck in his career and wasn't sure where to go. And he emailed me and he's like, man, you may not remember, but we had this one conversation and I'd reached out to you. And now I just finished as the number one top performer in this new company. I'm in this incredible place. I'm like, oh, okay. Oh, I'm good for like the next 5 years. That's amazing. Yeah. Wow.

1:26:28 Katie Jane Bailey: That's talk about energizing and talk about like a work vision statement. Like you are literally changing the trajectory of people's lives. Like that's incredible.

1:26:37 Scott Ingram: Wow. Yeah, that's my game. I'm enjoying it.

1:26:39 Katie Jane Bailey: Oh, you're killing it. I love it.

1:26:41 Scott Ingram: Okay, so book, book, book, book.

1:26:43 Katie Jane Bailey: Oh yeah, book, book, book. Okay, this is challenging. I'm debating on whether I say this one because it's a little bit vulnerable, but I'll go for it. I'll, I'll be vulnerable on, on the call with you, Scott. But so I basically, in 2020, and I think probably a lot of people can relate to this, so many things happened that were difficult that like as soon as we would start to like pull ahead, something else would just get dumped on all of us, you know? And I am calling it that we, we all gained emotional weight. So I know that's like so cheesy, but like, I think there are things that probably occurred in everybody's life. Like I got married last year and it was really hard to have a COVID wedding that were, you know, and everybody experienced something like that. Did you have a baby? Did you graduate? Did you, you know, pick some big life event and you suffered pain from it? And so I've been reading this book about basically like working through pain like that. And it's just really changed how I process things and, and move forward and prioritize. And, and I think that like mental health is actually really important in sales. And so it's not only affected just like my personal life, but it's also affected affected my professional life. So yeah, that's kind of vulnerable, but it's, it's a book that's really impacted me.

1:28:04 Scott Ingram: Yeah, what's the title of the book?

1:28:06 Katie Jane Bailey: So it's like kind of a sad name, but it's Walking with God Through Pain and Suffering. So pain and suffering is just like top of mind, like let's face it head on and talk about this.

1:28:17 Scott Ingram: Yeah, yeah, good. Thanks for sharing that.

1:28:19 Katie Jane Bailey: Yeah, I didn't anticipate sharing that, but there it is.

1:28:23 Scott Ingram: Awesome, awesome. What about kind of the tools and apps? What are you using from just kind of a tech perspective?

1:28:30 Katie Jane Bailey: Gosh, what am I using from… I mean, no one got to hear this, but in between we were talking about how we're not that great with tech even though we work in tech. From like what, you know what I mean? Like what kind of tech are you…

1:28:43 Scott Ingram: just kind of the core tools. Like maybe not… don't even think of it as tech. Like what, what are the core tools for you, whether it's apps on your phone, it's, it's things that you're, you're using just as, as part of your day-to-day process?

1:28:56 Katie Jane Bailey: Yeah, so I guess I'm not that big of an app person. I'm a really big personal finance person, so I've got my daily budgeting app that I use. We are a hilariously crypto family, so we're constantly checking all the crypto stuff. I would say that I try… I almost try to… I don't know, I almost try to like not be that engaged because I'm on the computer all day So yeah, other than just like, I don't know, recipe apps, Instagram, those are probably, you know, my, my break away from normal day-to-day. That's not that interesting, but that's, that's what it is. Yeah.

1:29:33 Scott Ingram: What's, what's the daily budgeting app?

1:29:35 Katie Jane Bailey: It's EveryDollar, Dave Ramsey.

1:29:37 Scott Ingram: All right.

1:29:38 Katie Jane Bailey: Oh yeah, I love it. It's great.

1:29:39 Scott Ingram: Excellent. How do you think about technology? And maybe you haven't like actually thought about this, so maybe I'm, I'm gonna have you like think out loud. Do you think of some of this tech more as like, this is a tool, this is enabling me, or do you see it as it's often a distraction?

1:29:58 Katie Jane Bailey: You know, I think so. I take everything back to Figma, but it's clearly a big part of my life right now. So Figma is an online collaboration tool and it basically means that kind of like the difference between Microsoft Word and Google Docs, like that's kind of what Figma does. So you can design at the same time as other people. And we hear stories from people all the time about Figma, like, again, changing the trajectory of their life, or this allowed me to have a job during COVID or this, my career, you know, I had to move home with my family and I wouldn't have been able to have a job if I didn't have a remote design tool, you know, so these like really powerful stories that come back to being enabled by technology. And that's super moving. And that's something that is really cool to be a part of. And then I think about like Zoom, right? Super basic, or even this, this recording software we're using now. I mean, I wouldn't be able to be talking to you right now and like having this wonderful experience had it not been for technology. So I think that I think that the way that technology can enable us can be super, super powerful. And I also believe in boundaries with technology as well. So, being able to, you know, like, I mean, we've all experienced this like to the nth degree this year of, I miss being around people. I miss parties. I miss, you know, the office. I miss, you know, seeing people and drinks, getting drinks. And so, Zoom can never ever replace that. A video conference can never replace that. So how do we shape our lives around… how do we let technology come into our lives and enable us and open up opportunities that never would've been there before, but also have boundaries? Yeah, I guess that's my thought on it. What's your thought?

1:31:55 Scott Ingram: I like it. I like it. See, there you go, turning this around again.

1:31:58 Katie Jane Bailey: Well, you talk to so many interesting people, you probably have like these conversations all the time.

1:32:03 Scott Ingram: Yeah. You know, actually, especially when I started this podcast, I theorized that the very best salespeople were ones who just had like this mystical control of their tech. Like they, they just, you know, I, I had this idea that they had kind of built these amazing tech stacks for themselves and they had figured out how to be superhuman. And in a lot of ways, I have actually found the opposite. I find more and more top performers who use less tech.

1:32:37 Katie Jane Bailey: Hmm.

1:32:38 Scott Ingram: And I don't know, I don't know if it's more of a focusing on the humanity. I don't know if it's, you know, a couple of years ago, or maybe it wasn't that long ago, I noticed a theme of a lot of people talking about they do all of their note-taking by hand.

1:32:53 Katie Jane Bailey: Oh, yeah, totally.

1:32:54 Scott Ingram: And I did some research on that. And it turns out your retention is 3 to 4 times.

1:33:00 Katie Jane Bailey: No way.

1:33:01 Scott Ingram: Taking, taking notes electronically and things like that. And I think it's kind of a balance. You know, I, I generally, the way that I think about technology is you have to use it as a tool. You can't be the tool. You can't get used by your technology. And I think in a lot of ways we do, especially when we think about social, you know, like you're getting used. So you really have to kind of figure out, and, and again, I think you said it well. It's, it's kind of having the boundaries and going, hey, I'm using this for this purpose and I'm not going to let it suck me down this rabbit hole that it's trying to, that's going to keep me from doing meaningful, productive work.

1:33:39 Katie Jane Bailey: Yes. Yeah, exactly. Totally agree. Yeah.

1:33:42 Scott Ingram: It's been a really interesting process of discovery and I wrestle with it all the time. I love my tech. Like I have a lot of tools, a lot of different things that I use, but I really do try to at least be mindful about it and think about like, do I really need this? Is this really the best process or am I just overcomplicating this? And, you know, I mean, it's similar to… I have… it's not a hard and fast rule, but anytime more than, I don't know, 4 or 5 texts get exchanged, it's probably just time to call.

1:34:13 Katie Jane Bailey: Yeah, totally, totally.

1:34:14 Scott Ingram: Why are we trying to do this? Why don't we just talk? This, this would be so much better.

1:34:19 Katie Jane Bailey: Yeah, yeah, I agree, I agree. I know, I'm like, golly, what does it say about me that my tech is like recipes, budgeting, and like Instagram, you know?

1:34:27 Scott Ingram: Well, and again, I think you're, you're proving, and it is kind of a counterintuitive thing. We… because we… with the amount of tech that we're surrounded by, you would think, oh, I'm missing out. But it's a scenario where I, I think in a lot of ways less is more.

1:34:42 Katie Jane Bailey: Yeah, no, totally. Well, and you know, when you're in tech sales and you're working in like… your tool stack is by the dozens, it's… you're just so in it that, you know. So, and I mean, very powerful, lets me do my job, love it, but also happy to go for a walk at night, you know.

1:34:58 Scott Ingram: Yeah, awesome, awesome, awesome. So you mentioned SPIN selling. Do you subscribe to a particular sales philosophy?

1:35:05 Katie Jane Bailey: Not yet, no. I guess my philosophy is, uh, discovery is a lifestyle. I'm just kidding. I don't. I mean, I guess I think that what has led me to be successful is my question asking. And so if I were to analyze my calls, you could… it probably would fall into one of those categories. But no, I think… is that a bad answer? No, I think it's totally fine.

1:35:33 Scott Ingram: Here's the other thing that I'm observing, because you're not kidding about discovery being a lifestyle. I mean, the setup here is like, I get to interview you. My job is to interrogate somebody else, and, and that's kind of the setup. You have asked me more questions than any other person I've ever interviewed. It is awesome. No way. It's awesome. And I think it really proves the point, right?

1:35:58 Katie Jane Bailey: Yeah, totally. Well, I mean, I'm Like, I've been excited for this conversation, and I really see it as a conversation, you know? So, yeah.

1:36:07 Scott Ingram: This is gonna be so long.

1:36:09 Katie Jane Bailey: I know. Everyone's like, we have like 3 people still hanging on.

1:36:13 Scott Ingram: No, you know, here's what's interesting. I mean, my audience has been with me long enough, many of them, and people tell me, they send me notes and they say, I know when it's really long, it's really good.

1:36:27 Katie Jane Bailey: No way, really?

1:36:28 Scott Ingram: Oh yeah.

1:36:29 Katie Jane Bailey: Oh yeah. Oh, I love that.

1:36:30 Scott Ingram: They know. So, you know, when, when we cross the 2-hour mark, which is starting to become like a real possibility with this one, even with our like, oh my God, speaking of technology, yeah, maybe disabling us. We almost had a disaster, but we're, I think we're all good.

1:36:46 Katie Jane Bailey: We're good.

1:36:46 Scott Ingram: Yeah. This is gonna be an epic, but I think it's gonna be a good and important epic. So thanks.

1:36:52 Katie Jane Bailey: Oh man, that's awesome.

1:36:53 Scott Ingram: Thanks for hanging in with me.

1:36:54 Katie Jane Bailey: And of course.

1:36:55 Scott Ingram: Going as deep as we're going. So, like stylistically, if you were to name your style or describe your style, what is that?

1:37:06 Katie Jane Bailey: Yeah, so I think my style is, well, I don't know exactly, but I'm gonna describe it. So, I think because I have this like natural hosting tendency, so like when I meet someone for the first time, I'm like, tell me all about you, where are you called, like who are you, what's your story, you know? They almost assume that I'm kind of this like soft salesperson that I'm gonna, if they ask for it, I'm gonna provide it, you know, and all this stuff. And so just when they think I'm gonna be Mr. Nice Guy, I turn around and I'm like, oops, sorry, turning off trial. Really sorry. You know? And so I think that is like knowing how to leverage relationship building, like as a I don't know, as like a style. So like, how do you kind of bring someone in but also set boundaries? Yeah, I guess a hosting but knowing when to turn off the… shut the door kind of style. I don't know.

1:38:02 Scott Ingram: I don't know what this…

1:38:02 Katie Jane Bailey: I don't know how to describe it.

1:38:04 Scott Ingram: This has been a really fun party, y'all. Now go home.

1:38:07 Katie Jane Bailey: Go home. Yep.

1:38:11 Scott Ingram: Oh, I don't know that we have a word for that, but that's okay.

1:38:13 Katie Jane Bailey: Okay, perfect. I'll think about it. I'll like email you. I'll be like, this is my style. I finally thought about it.

1:38:18 Scott Ingram: There we go. There we go. One of the things you can do to solidify your relationship with a great hostess like Katie Jane, or any relationship really, is to bring a gift. It's even better if you give them a really personalized gift. Now imagine if you were to incorporate personalized gifts like that into your sales process. Wouldn't that be powerful? Well, it's exactly what Alyce does. They have an incredible personalized gifting platform platform that will not only deliver the gifts but also recommend something that your recipient is likely to love. Even better, it will let them choose something else just in case you didn't hit the mark. It's pretty amazing. Check them out, top1.fm/Alyce. Speaking of great gifts, let's get back to Katie Jane. What about motivation? What motivates you? How do you think about motivation? Like, what, what drives all this?

1:39:15 Katie Jane Bailey: Yeah. Okay. So motivation is super important because what we do is hard and you have to find it in you to continue to like taking each step forward in sales. For me, I'm very competitive, so that's definitely a motivation. I'm super goal-oriented. And so if I set a goal, it's like almost a problem because I work so hard to achieve it. And I am results-driven too. So I think my motivation is, am I setting myself up in a situation where I can be competitive, I can be results-oriented, I can take risks, and I can have, you know, pursue really big challenges? And if I find that setting for myself, then And I will, because those things all naturally fit my motivation, then I will continue to propel forward. So yeah, I think I would say, have you heard, I'm sure you've heard this, do you love winning or hate losing? I would say that I hate losing and that, that is like, all right, if we started this, we have to finish this, which is probably a big motivation for me.

1:40:32 Scott Ingram: Okay. Um, 2 follow-ups so far.

1:40:35 Katie Jane Bailey: Yes, yes.

1:40:36 Scott Ingram: The first is, what are your goals as they relate to your sales role?

1:40:43 Katie Jane Bailey: Hmm. Well, a big goal for me this year is helping to build a world-class sales team. So that is actually a goal which sounds like a really non-measurable one, but if you add measurables with it… so like, I have a goal for myself around closing rate. So that's, that's a goal we have. Like, we call them strategic or our velocity deals. So I set a goal for how many of these like large strategic deals I want to close in 2021. And I also like, I don't know, this is like a really weird goal, but just to hit or exceed quota is like such a basic goal. But at Figma, because we were, we used to be heavily inbound and now we are heavily outbound. Found, everything changes. And so if you're just trying to exceed quota as your goal, it sounds like, yeah, you're a salesperson, duh, that's like the goal. It means you have to, we have to ask deeper questions of how to succeed. And so that forces us to look at recaps of other deals to try to replicate that success, prospect even more, ask deeper questions, get to executive narrative faster. So you, you kind of pick these like high-level things that trickle down to like, this translates to good habits.

1:42:02 Scott Ingram: I'm curious, you didn't name the specifics of, of some of those goals. Why?

1:42:07 Katie Jane Bailey: Like which one?

1:42:08 Scott Ingram: You said like the number of deals or what the close ratio was without naming any of the numbers.

1:42:14 Katie Jane Bailey: Yeah. So I don't know. I, I feel like, I guess it doesn't really matter, but so there's like number of ops and then dollars close rate. My dollars close rate is 62% and my ops close rate is 47%. And I would like to see my ops close rate go up to that dollar close rate.

1:42:32 Scott Ingram: Got it, got it.

1:42:33 Katie Jane Bailey: So that's one. And then the other one, I didn't say any numbers around like strategic versus velocity, 'cause I don't know if it resonates with people, but it's basically like a velocity deal is like a $27K deal size, and a strategic deal is like $100K to $500K deal size.

1:42:52 Scott Ingram: Okay. Yeah. So I'm also really interested in, given your hypercompetitive YC firing.

1:42:59 Katie Jane Bailey: Yes.

1:43:00 Scott Ingram: How are you resolving that with the world-class sales team concept? Because I think that's one of the things that potentially gets in the way of, of what we're talking about earlier. So how are you thinking about that?

1:43:13 Katie Jane Bailey: Oh my gosh, that's like… you're such a question… you have great questions, Scott. It's the elephant in the room. Like, it's like, how can you be competitive and on a team, you know? I mean, we're all still going to be competitive for sure. We all want to be number one. And I I think so. Okay, so my, like, the other guy who's the number one on our team in terms of like quarterly bookings, he and I have now started trading calls doing peer feedback. And that's like so counterintuitive, you know, like the 2 top competing people on the team being like, can you review and give me feedback to help me get better? And I think that is a good example of basically seeing that we can get better from each other and acknowledging the elephant in the room, but also like taking action on intentionally trying to be teammates.

1:44:03 Scott Ingram: Yeah. It's not always easy, but I think it's, first, I think it's fascinating that you actually have a goal around world-class sales team, right? Because at some level, that's, that's going to help, right? The other thing is, I think there's 2 kind of styles in the way that people want to compete. So one is the, I want to be the best amongst the best, and, and I only feel like I've fully won and I'm number one if the people that I was competing against were at the top of their game too. Totally right. So that's one, and obviously there's the flip side of that which is, hey, I can be number one no matter how I get there. And if that means I had to tear down number 2, or the person who was going to be number one, like, okay, well, that's messed up and toxic. I think the other thing that you can do is be competitive about being the person who is the most helpful or is the most, you know, I talk, I haven't probably talked about this publicly on this podcast in a long time, you know, folks can go back and listen to the time that I got interviewed on my own show. That was back in episode 62 with Jeff Bajorek. And my why I talk about as inspiration squared, right? Because I love to be surrounded by inspiration. I love to be around people who inspire me to do more and be better. But I also want to do things that people see and are also inspired by, right? So that's how I think about sort of the 2 sides of inspiration.

1:45:41 Katie Jane Bailey: And so, if you can be competitive in your helpfulness, in your selflessness, yes, totally. Yeah, I love it.

1:45:52 Scott Ingram: Something to think about.

1:45:53 Katie Jane Bailey: Yeah, I love it. Totally.

1:45:55 Scott Ingram: Think about. So, is there something you believe that the average sales professional would think is crazy?

1:46:04 Katie Jane Bailey: Hmm, probably. I mean, I think the first thing that comes to mind is that I think there's strength in the whole difficult conversation, adding friction to a relationship. I think that is counterintuitive to a lot of salespeople if I had to guess, but I don't know. So I think that's one. But other than that, I think I, I believe all the things that everyone else preaches as well. I don't know what, do you think a lot of people would agree with the whole friction I think so.

1:46:38 Scott Ingram: I think that that is a fair thing. Actually, what I was thinking of is people may not hear it because it just happened. There's friction in questions and the friction is often in the silence. And so what people don't hear in this podcast, we don't cut out a lot. I cut out very, very little, but we cut out a lot of the you taking time thinking about like, gosh, I don't have an immediate answer to that. And so the friction for me is I just have to shut up and wait.

1:47:15 Katie Jane Bailey: And wait. Yes. Yes.

1:47:18 Scott Ingram: Right. So I think it's hard.

1:47:19 Katie Jane Bailey: Oh, yeah.

1:47:20 Scott Ingram: It's so easy to just want to step into that space. And it's so powerful if you don't.

1:47:28 Katie Jane Bailey: If you don't, if you just sit there.

1:47:30 Scott Ingram: Yeah.

1:47:31 Katie Jane Bailey: Yeah. Yeah, totally. I guess no. I mean, maybe, but maybe not. I mean, I think there's a lot of great people doing a lot of great work in sales that I love learning about and usually hear and go, yeah, yeah, I agree with that.

1:47:44 Scott Ingram: Yeah. Yeah. What, what about the flip side though? Is there something that the average or the typical sales professional believes that you think is crazy?

1:47:51 Katie Jane Bailey: You know, I think that, and this is maybe like salespeople, but also just like people in general about sales. I think that a lot of people think the only motive motivating factor for salespeople is like commission, you know, like, like referring to people as like a coin machine or whatever that phrase is, you know, like that's what people are motivated by. So just give them that opportunity and they'll work harder. And I don't think that's the case with a lot of salespeople. And I think that motivation and inspiring people and helping them to be better at what they do is a byproduct of like, you know, making a good commission is a byproduct of that. But I actually think that that is only for motivation for salespeople?

1:48:34 Scott Ingram: Yeah. It's one of those things I wish that I, well, I guess I need better questions to do it justice, but, but an area that I wish that I had consistently dug into more with, with folks, because I think you're totally right. I think especially among the top performers, I think there's, there's a level where, I don't know, it's kind of almost survival. Survival, right? There's, there's a certain level of drive if, my God, like, I have to get to this level because I gotta pay my bills, I gotta feed my family, I gotta, you know, I gotta, I gotta take care of the super stressful stuff. But at a certain point, that's no longer really an issue. And is the money really as motivating at that point? And I think it's… I, I don't know, maybe it's, it's more like Maslow's hierarchy of needs sort of stuff, right? I think becomes bigger than just the dollars. Like once you know, okay, I'm gonna have a place to live, I'm gonna be able to eat, my children aren't gonna go hungry, they're gonna have shoes.

1:49:38 Katie Jane Bailey: Yeah, yeah, yeah.

1:49:39 Scott Ingram: After that, you know, I think the dynamic changes a lot. And, you know, it's, it's one of those areas that we work with Terryberry as, as one of our sponsors, and I may or may not have mentioned them earlier. I don't know, probably not, because I've got a couple new sponsors I have to talk about. But it's, you know, they've dug into this a lot. And, you know, really looking at what are those true drivers, and we might even say money. Because it's, it's kind of the right thing to say. But yeah, it's bigger than that. It's way bigger.

1:50:17 Katie Jane Bailey: Yeah, there's like a couple of months ago, so we work pretty hard long hours at Figma because there's just so much going on. And I remember thinking to myself, you know, Figma could like put more incentive financially in front of me, but that is not going to make me work harder. Like I am at capacity for how hard I can work. And what they could do is they could incentivize me somehow to work smarter. So I have 8 hours of the day, 3 of which are golden hours. And then every once in a while you put in a 9 or a 10-hour day or 12-hour day, you know, and like that is the full amount that Figma, my company, gets from me. And if they gave me a substantial amount of money to say, can you work 12 hours a day? I would say no. Like, I would be like, I'm not interested in, in more money. But you can incentivize me to figure out how to do better with the hours that I have. And I don't know what that kind of incentive looks like. Like, how do you, how do you reward, or how, what kind of structure can you put into place to reward someone for like, like that? But it was this interesting moment of like, this is not my big motivator, but I do know I can get better. And I wonder what it would be like for companies to incentivize that kind of behavior.

1:51:39 Scott Ingram: Yeah. Well, if you want to hear somebody who's done that, go listen to Matt Du Pont.

1:51:46 Katie Jane Bailey: Okay.

1:51:46 Scott Ingram: So I interviewed Matt about a year ago. He'll be coming up here soon in the Encore Series and kind of his replay from his session from the Sales Success Summit. Yeah. Matt, in his previous job, he basically negotiated himself down to a 3-day workweek because he could accomplish in those 3 days. He was number 1 in 3 days a week. Week. Because he, because he did exactly what you just described, right? He is smarter, so insane with the way that he uses his time and he may, and the way he measures it and the way that he self-optimizes.

1:52:24 Katie Jane Bailey: That's really my goal.

1:52:25 Scott Ingram: It's like, look, I don't need to make more money. I'm just trying to earn myself more time so that I can spend time with my family and, and do these, these other things.

1:52:34 Katie Jane Bailey: Yeah, exactly. Exactly. Okay. I'm hooked. I'm going to go listen.

1:52:39 Scott Ingram: Yeah. And for everyone, so top1.fm/encore is where you can go to sign up for that series. And Matt just changed dates. Oh gosh. I hope I, I might've screwed up the timing on this. This may have passed, but either way, the recording of that session is available. And if you join the listener list, if you're not already on it, or heck, if even if you're on it, send me a note and say, hey, I missed Matt's thing. Will you send me a video and send me the code, I will hook you up. scott@top1.fm is your secret way to access that. Let's talk just a minute about the career side of things, especially coming from the non-traditional space that, that you came from. I guess the first question I would ask is, knowing what you know now and knowing kind of your journey through sales, if you were starting over today, is there anything that you would have done differently or a different way that you would have approached your career?

1:53:36 Katie Jane Bailey: You know, this is so funny. I was listening to one of your conversations recently with someone else on the show, and when you asked this question, it made me ask myself, and I thought about it, and I tested some ideas on myself, like, oh, would you have done this? You know, and, you know, I don't know if I would have done anything differently. You know, of course, like, you know, having done musical theater for 4, 4 and a half years, it put me a little bit behind in terms of of like not age range, but like number of years out of school, where you are, whether you're a rep or a manager or things like that. And, and then taking like, because I have had no experience working at a smaller company instead of going straight into like kind of a bigger, you know, bigger company. And so I look at my career and I compare it to people at my company and, and mine is so different. And there are things that I did not learn learn early on that, that I can see shaped other people. But there are things that in musical theater that shaped me in ways that are so valuable. And then in terms of starting out like on the sales side, you know, I learned a lot of lessons the hard way by just doing it, you know, like just getting at-bats, just going to town on prospecting and doing the full sales cycle. And, and I think that some of the lessons that I had to learn were, You know, like the whole concept of working as a team, that has been a huge evolvement in my career. When you're in musical theater, it's the ultimate lone wolf and you have to, I have learned to break those habits in order to transition into this team mentality because I see the benefits and I see that that's where I wanna go. And so it's really hard for me to say what, what would I have done differently? And I, I think the only thing I would say is when I made the career transition into sales, I wish I would've known about all of the sales resources that were out there, even at that time, which was 6 years ago. And like, like SPIN Selling and Challenger Sale and like all these different books, Fanatical Prospecting, you know, and I just didn't know about them. And so I think I would say read sales books, read, listen to sales podcasts, like try to find other people because I was very limited in the type of information I could consume and therefore limited in my growth because I wasn't exposed to what is out there to improve upon, essentially. So, that's a very long answer to, I would tell myself to explore more resources.

1:56:11 Scott Ingram: Yeah. Yeah. Is, is that the same advice that you would give to somebody that's, that's kind of coming into sales?

1:56:17 Katie Jane Bailey: I would. Yeah. I think that, you know, sales is not a degree, right? And so, you can't, like, people think you can't study sales, but I actually think you can. And especially especially if you're in a sales role and you read these books or listen to these podcasts, it's very applicable information. And, you know, especially this, your podcast, listening to top performers. I mean, I was like with Kyle Rasmussen the other day, like that shaped me and my prospecting as a full cycle rep. And so I have friends who I like to help people who have a non-traditional background get into sales. So I help them with like interviews and, and things like that. And a good friend of mine who was, came from the nonprofit industry just got job at salesforce.org, and I was like, okay, you got to listen to sales success stories. You got to like read this because it's going to help you get better faster and you're going to grow in your career with more exposure.

1:57:09 Scott Ingram: Love that. Love that. What do you see? Because Marissa brought this up too. I mean, she, you clearly are a great team player, right? She, she kind of pointed out the way that you're helping others on the team, helping her, helping people get into sales. When you're bringing those folks from non-traditional backgrounds into sales, what are you telling them? How are you helping them through this process? What are there things that you sort of see consistently or, or, you know, misconceptions that maybe they have about what this really is?

1:57:39 Katie Jane Bailey: Yeah, so I like to really push them on their story and like really kind of like make them narrow in on why their previous experience is fit sales. So like, for example, I helped a really good friend who was doing like eyewear sales. So outside sales, going door to door to these, you know, doctor's offices selling this eyewear. And he just crushes it. And he was like an NCAA diving champion. So just the perfect makeup of a very successful salesperson. And he wanted to switch into inside sales at a SaaS company. And so, you know, it's sales, like it's the same motion, but when you're moving into like a SaaS sales job versus an outside sales job, that like recruiters, they, that's like a breakdown for them. They're like, oh no, this isn't applicable experience, you know? And so I basically would be like, okay, his name's Dom. Dom, how is what you've done, how does that translate to what you do now? Why, why are you going to be successful at this? What are some things that you wouldn't necessarily think show success criteria and how do you help that recruiter to understand that? And so, I kind of push them to see that what they've done, like for example, fundraising in the nonprofit industry, that's sales. Like auditioning, that's sales. Going door to door selling eyewear, I mean, that's such hard sales. And so, it's basically helping people to translate their previous experience into what they are applying for, helping them to learn that vocabulary, Helping and pushing them to own their narrative, essentially. Yeah. And people… and happy to say Dom is now working at Udemy, doing great. And it's super fun to help people with that.

1:59:26 Scott Ingram: Yeah, love it, love it, love it. What about folks that are further into their career and maybe they're struggling, maybe they're stuck, maybe they're good, but they're, they're not like Katie Jane level yet?

1:59:39 Katie Jane Bailey: Oh man, that's too nice.

1:59:41 Scott Ingram: What do you them? What do you tell folks that, you know, they're in it, they understand what this is, and they're ready to go to the next level? How do they get there?

1:59:49 Katie Jane Bailey: Yeah, I mean, I think like, what is the next level, right? Like, is the next level a different company? Like, is the next level a promotion? Is a next level like reprioritizing? Like, maybe work isn't… maybe next level is starting a family, you know? Like, how do you define next level and how do you you connect the dots from there? You know, how do you find the golden thread? So let's take someone, let's, let's use one of your, let's use an example. So let's take someone who's been in sales for enterprise sales. They're a senior AE at a company. Let's just use like Salesforce, you know, they are probably not on track for a manager because they close all these large deals. It's just not quite in the cards. And maybe they haven't really shown kind of, you know, an interest in being a manager, but in their head, that is the next level. Well, You know, how do we open up that idea of what that looks like for them, right? Like, let's say that every rule around career trajectory doesn't exist. What are the things that get you going in the morning that you can find that kind of opportunity? Like, a senior AE at Salesforce who has 5, 7 years of experience, some of these smaller companies would die for that kind of hire. And you could go from being a little fish in a big pond to a big fish in a small pond. And all of a sudden you're mentoring all these salespeople, brand new salespeople around you. Like, does that sound like next level? And so I think it's, it's releasing ourselves of, I must get to manager, I must get to director, you know, like how do we explore where we want to go with our next step essentially?

2:01:25 Scott Ingram: Yeah. Yeah. Where's your path headed?

2:01:27 Katie Jane Bailey: My path? Oh yes. Where is my path headed? So I am finding that But I really love working with people. So, like, I even borderline thought about, like, I wonder what it would be like to have a consultancy where I help non-traditional people get into sales because that was my background. And so, when I help someone with, like, a deal that didn't look like it was closing and it now closes, like, that is so fun to me. We're starting this thing on our team. I'm, like, kicking it off and it's called the Disco Club, which Which is like basically sending each other our discovery calls and giving peer feedback. And people are stoked about it. Like they're, you know, they see an opportunity to improve. And so I'm really excited about working with people. And I know I've said this like so many times, but I'm really excited about building a world-class sales team too. Like I'm excited about being, holding ourselves accountable to really tough metrics and working together to achieve those things. And so, for me, this is again, maybe not a great answer because I'm not 100% clear on where I want to go, but I know I want to be working with people. And so, you know, maybe that is manager, director leading a team route. Maybe that is consulting. Maybe that's, you know, I think it would be super fun to help build out a small team for early stage companies and get them going. I just don't. Don't, I don't know yet, but I'm having a lot of fun even exploring it.

2:03:02 Scott Ingram: Yeah, that's awesome. Yeah. What would you want to know about the top sellers in other companies?

2:03:10 Katie Jane Bailey: I would want to know, are they super good at the most basic sales habits? Like, do all the top sellers always set, you know, like the pre-call email, the next call discover, you know, proper discovery? Like, are the top sellers, are they actually really good at the sales hygiene? I would love to know that. What do you think? Do you think they are?

2:03:34 Scott Ingram: Well, do you think you are?

2:03:35 Katie Jane Bailey: I think I'm good at it, but I'm not great at it. So I think I can get a deal done and I think I can always improve on all of those things, which is part of Disco Club is creating that accountability. But yeah, so I, I, I'm, that's a very good response, Scott. So I think that's why I want to know, is like, is that a key thing that people have like doubled down on and that's what makes them great? Or yeah, I don't know, I'd be curious.

2:04:09 Scott Ingram: Yeah, so I had some fun deflecting the question there, but yeah, I think really the answer is it kind of depends. I think it comes down to sort of a stylistic thing. One of the things that I really hope people understand in listening to these conversations is the very best have figured out what works for them. They've kind of found their way. And so the reason I say it depends is there are some people who are just crazy process driven, and they've got their process really dialed in, and they're fine-tuning all those little elements. And I would say they are probably the absolute masters of the basics because they, they just make sure that this is the way I do it, you know, right? They're, they're kind of looking at it, they're looking at those opportunities to improve each component, right? And, and I mean, shoot, maybe I order people into kind of the scientists and the Right. So I think that's more kind of the, the pure scientist approach. And again, this is kind of a spectrum, right? And then you've got a more artistic approach where it may be a little bit more nuanced. It may be a little bit more kind of seat of the pants, you know, not quite as structured. And again, we're all different. What, you know, what, there are things that you're doing that you can do that if I tried to do them and act like you, it would just be an abysmal failure. Yeah, I'm not you. I can't do you. Yeah, but I can do great Scott.

2:05:57 Katie Jane Bailey: Yeah, yeah, totally.

2:05:59 Scott Ingram: And so I think that's really the game, right? As we think about this development and we think about this growth, it's understanding yourself and kind of figuring out what works best for me. What are the things that I can work on that's going to make the biggest difference. Did you call it peas and carrots earlier?

2:06:20 Katie Jane Bailey: Yeah. Yeah.

2:06:21 Scott Ingram: Right. So yeah, maybe, maybe you got to work on the peas and carrots or the blocking and the tackling or whatever you call kind of those fundamental, you know, core actions. And there's an opportunity to just fine-tune each of those, or maybe there's a bigger thing. Maybe you need to work on being more comfortable in silence or in the friction, or, you know, again, like there's so much that, and to me it's just one big experiment.

2:06:49 Katie Jane Bailey: Yeah.

2:06:49 Scott Ingram: You know, like there's so much opportunity to just play with this and try this. I mean, before we got on this, I told you a story of kind of stuff that I'm working on, man. I was making stuff up as I, as I went through that, quite literally. I said I was making stuff up. I told the client that and they said, oh, you know, we need to spend another $100,000.

2:07:08 Katie Jane Bailey: You're just, yeah. Yeah, totally. It's, you get to play, you know? Know, like, that's the fun of it. Yeah, totally. Yeah, it's so true. And, and I think that there's not a whole lot of careers that you get full autonomy. Like, you're driving that call, you get to do whatever you want, you know? Yeah, focusing in on… and so just knowing yourself better. And you can only know yourself better if you're honest with yourself as well. Yeah, I love that.

2:07:34 Scott Ingram: So you did… I could tell that you did quite a bit of kind of prep and thinking and, you know, work towards this interview, is there a place that you were hoping to go or a question you were hoping I asked that's like somehow we didn't get to?

2:07:48 Katie Jane Bailey: This is really weird, but I think that, and I actually say this at Figma because I think that it's easy to forget, but I think that sales is a very hard job, even in the highs and the lows and the fun and the wins. And I just think that it's sometimes like in some companies, you know, salespeople have a certain reputation, or even if that is not true at all, they still have that because it's sales. And I just wanna like basically say that I just think sales is the most incredible work people can be doing and that it's like so encouraging to have a community like this where people can come and feel supported. And like, and learn and explore. And so, I think that was the only thing that I was like, I would love if we could talk about that a little bit. But other than that, we covered, we covered everything.

2:08:49 Scott Ingram: Well, let's, let's talk about that. I mean, that is such the greatest intro. And during our near tech disaster, you and I had a little sidebar and you unilaterally committed yourself and Marissa to joining us at the Sales Success Summit in Austin. October. And, you know, to me, the way that I think about that is it's community. And it's also, I don't know, this isn't going to come out right. The word that's floating in my head is like trade association or something. So, Evan Kelsay did a really great job of articulating this after the summit in 2019. And he wrote a piece on LinkedIn called Steel Sharpens steel. And the way that he framed that story, he was talking about his wife who's a doctor. And in every other profession, whether you're a doctor or a lawyer or you're, you're a CPA, those folks all have practices. And they have continuing education requirements. And more importantly, they tend to have have some type of association. There's a group of people that are all kind of committed to that practice, to that craft, that get together and are committed to learning from each other and, and kind of continue with it. And I, I think it's not, it's not nearly as prevalent as it should be.

2:10:21 Katie Jane Bailey: Mm-hmm. In sales.

2:10:23 Scott Ingram: That we treat sales this way. I really do. It's… I ask people about this a lot, and the most common answer I get, it's not even 80/20, it's probably 90/10. You know, it's, it's 10% of sales professionals that really view what we do as that level of, of profession and craft and are, and are committed to it in this way. And yeah, I mean, the beauty is I attract them. They like these 2 and a half hour interviews, and they geek out on them, and they get all excited because it's so damn long. Yeah, to me it comes down to that community, and it doesn't need to be everybody, right? Like, yeah, you, you are here, you have found your people, and we just love this. Like, we love to help each other. We get so excited by the growth. We get so excited by our ability to help our customers achieve the things that they want to achieve. And I love this kind of world-class sales team theme that we're on, because the tagline for this show since I started has been deconstructing world-class sales performers.

2:11:31 Katie Jane Bailey: Oh my gosh, full circle. Amazing.

2:11:33 Scott Ingram: But that's individual.

2:11:35 Katie Jane Bailey: Oh yeah.

2:11:37 Scott Ingram: And I've been thinking about this and starting to talk about this a lot as we think about kind of the broader ecosystem and the way that we support sales, because we need to focus more beyond the individual. Right. And think about the community, think about the team, think about the profession as a whole, because you're right, it's changing. I really believe that minds are starting to change. A lot of the stereotypes are beginning to fall away as people get exposed to great sales experiences.

2:12:09 Katie Jane Bailey: Yeah. Yes, 1,000%. Yeah. One of my, this is like, I'm totally just going to brag for a second here, Scott. One of One of my proudest moments at Figma was one of my customers that I brought on board was Spotify, and it was so fun working with Spotify. And one of their designers… design Twitter is a really big thing… and one of their designers, she's like a principal designer, someone had talked about like a bad experience with salespeople, and she replied, not Figma, they have an incredible sales team. And I was the only salesperson she worked with. And I was like, that's me. Like, she's talking about me. And for someone to… and designers are especially like twitch when they hear the word sales, but like for a designer at such a high, it's such an established company and role to say that was just such a huge compliment. And it felt like, like a, I'm helping the industry and the people who are doing this, like, I'm helping, you know, like I'm helping be part of that change.

2:13:17 Scott Ingram: Yeah, yeah.

2:13:18 Katie Jane Bailey: Which was really encouraging. Yeah.

2:13:20 Scott Ingram: And you know, Spotify is a great place to listen to this podcast, just saying.

2:13:24 Katie Jane Bailey: Oh well, that's where I listen.

2:13:26 Scott Ingram: Well, of course you didn't even… I can understand why you were confused. You're like, wait, there's other places where people listen to podcasts?

2:13:35 Katie Jane Bailey: Yeah, I don't understand. A funny, really fast story from that deal is, uh, when I went to go to Sweden to meet with them, my dad gave me a feature request for them. I was like, this is… he still uses Pandora for certain, like, times that he listens to music because of how, like, basically good Pandora is in his opinion. And so he wanted them to create that same feature at Spotify.

2:14:03 Scott Ingram: Aha.

2:14:04 Katie Jane Bailey: It's very specific, but so, you know, I passed it along. They got it. They heard.

2:14:09 Scott Ingram: Fantastic. Fantastic. Katie Jane, this This has been incredible. Thank you for, for taking an ungodly amount of time with me. So, you know the deal, like the way I always try to end these is we talked about all kinds of stuff, but how do we now make it actionable for the person who listened to us forever? What would you challenge them to do over the course of the next week or 2 weeks to improve themselves and improve their results?

2:14:37 Katie Jane Bailey: You know, I would encourage people to ask themselves, how can I create a team culture within my team? What can I do? Who can I ask for peer feedback? Or who can I offer peer feedback? Or how can I take that upon myself to take that same mentality? And I would encourage people to just ask themselves that question. They don't necessarily have to do it, but you know, on the team that you are selling with, rate yourself. What could be better to move in that mentality? And is there, is that a good thing if you guys did that? And if people ask themselves that and then they take any action or do anything, oh man, I would love to hear that. I think that would be so cool.

2:15:25 Scott Ingram: Yeah. Yeah. So you're going to hear some from some folks.

2:15:28 Katie Jane Bailey: I can't wait.

2:15:29 Scott Ingram: It's kind of how this works, right? There are people who reach out to you on LinkedIn and I will say them, don't be shy. You know, what tends to be gratifying, and Katie Jane, I'm going to speak for you. You can tell me if I'm totally wrong, but…

2:15:42 Katie Jane Bailey: Yes. Yes.

2:15:43 Scott Ingram: The most gratifying thing is hearing that you had an impact. So, if Katie Jane impacted you with the things that she said, or you have now decided as a team, share this with your team, right? That what, what a great first step. Whether you're leading the team and you want to inspire everyone else to come together in this way, or you're on that team and you think like I do. I'm a huge fan of this idea that I call the intentional individual contributor. And in that role, I'm all about leading from the field. So there's no reason that you can't share this with the rest of your team, with the rest of your organization to get them on board with this and then reach out to Katie and reach out to me and say, I did it.

2:16:31 Katie Jane Bailey: Yes.

2:16:31 Scott Ingram: You know, and be specific about like, what was the thing? What resonated? Because those are the things that we love to hear that are making a real difference. So I guess that's my challenge to you. Share this with your team and then reach out to Katie Jane and I and tell us that specifically.

2:16:46 Katie Jane Bailey: How did they respond? Yes. What, what was your thing? How did they respond? What was the perception? Were they like, you're crazy? Oh my gosh, I can't wait. I'm gonna checking my LinkedIn every day to be like, okay, what did they do? What did they do?

2:17:00 Scott Ingram: Here it comes. We're going to have so much fun. And then stay tuned. Like I said, in 2 weeks, I will have another incredible, perhaps very long interview with somebody who was changed because of this show. And I can't wait to hear from them. You know, which episodes was it? What were the things that made it for them? It's going to be an incredible story. Thank you for joining me for this. Katie Jane, thank you for your time and your contribution to the Sales Success Community.

2:17:30 Katie Jane Bailey: No problem. Thanks for listening to the Sales Success Stories podcast.

2:17:35 Scott Ingram: To be sure you never miss an episode and for an invitation to our Sales Success Community powered by Influitive, subscribe to our newsletter at top1.fm.