134: Where Preparedness Meets Opportunity with Authenticx's Jenna Phillips

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0:21 Scott Ingram: 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 Visit us at top1.fm. Here's your host, Scott Ingram.

0:37 Scott Ingram: Today on the Sales Success Stories podcast, my guest is Jenna Phillips. Jenna was the top AE at Jobvite and has recently joined Authenticx as one of their first enterprise account executives. Also, a big shout out to Carly Montgomery for getting us connected. Welcome to the show, Jenna.

0:53 Jenna Phillips: Hello, thank you.

0:55 Scott Ingram: So let's kick things off like we always do. This is all about providing some immediate value, and I would love to talk through the top 3 things that you believe have contributed the most to your success as an AE.

1:08 Jenna Phillips: Great. Sounds good. Yeah. So the first one I would say is, is being quick on my feet. You could call this really just scrappy or, you know, I'm always problem solving and trying to think of new ways to, whether that's at the top of the funnel, getting into an account that we want to get into, or that's, you know, a roadblock later in the funnel where You know, we can't get past security or we, you know, all of a sudden need to bring in a different team member. I have some examples I could get into later, but I think the role of the account executive is getting the deal across the line as quick as you can. And a lot of times roadblocks are going to come up along the way and being able to quickly adapt and think of ways to get past those has been huge for me. And then secondly, it's, it's really the quarterback mentality. So especially, you know, I'm in enterprise software sales, right? And even mid-market SMB software sales, that account executive is just one small, small piece of the puzzle in the deal. And so bringing in everyone that you can from your organization to make the deal get done has been big for me. And I really pride myself on getting to know my coworkers as quickly as I can and as in-depthly as I can so that when You know, obviously just because that's great all around, but especially because when you're in the deal and you need a last-minute, you know, solution engineer to hop in, but their calendar is blocked, they're willing to step in because they're invested in your deals with you. And, you know, they become just as excited to see the deal close as you do. And so they're willing to put in more effort and better quality work than, you know, maybe they are for some other account executives. And keeping in mind, You know, people don't trust salespeople. So the more that I can get other people to join my deals and speak to whether it's a product feature or a why, like how it worked for them when they were a customer, when they were in the role that this person is now in, is, is huge and goes really far. And then the third one is, is really building quick trust with my prospects. So, you know, relationship selling kind of Gets a bad rap, I think, in the software sales sometimes. But I think starting that way at the beginning of your deals so that you get that really good trust and you can move into more of the consultative and strategic challenger type sales when you already have that trust built.

3:41 Scott Ingram: Yeah. So it sounds like trust is kind of emerging as a theme here, right? It's the trust that you have with your team and being able to leverage them to build trust with your prospects and then the way that you're building trust yourself. So let's talk about that piece. I mean, how are you really approaching that and trying to make that happen early in the, in the sales cycle?

4:01 Jenna Phillips: Yeah, absolutely. I mean, there's little things that can show trust in a big way, right? Saying what you're gonna do, right? So that upfront contract, right? If you, not only does that set the ground for the first call, but then when you do what you said you would do in the upfront contract, that builds the trust. But then, you know, Personally on my sales calls, and actually my current boss will laugh about this because sometimes it's very much not his sales, his sales persona. So I'm very casual on my calls. I'm very kind of lackadaisical with people. And I think it just takes down the wall of like, oh, I'm talking to a salesperson and makes them feel like they're just talking to a person and allows them to open up a lot more. I mean, obviously I think about ways we can connect and whatnot, but It's not about, oh, where did you go to school? I went to school there too. That's not the kind of rapport building I do necessarily. It's more thinking about the role they're in and the pain points I know they're in and empathizing with them right away and showcasing that, you know, at Jobvite, I had been a recruiter. And so that was really easy to be able to say, oh gosh, I remember those days, or I know that, right? The role I'm currently in at Authenticx, I've never been in the role of these people. But I've talked to a lot of people like them. And so being able to empathize with them, show that I know where they're coming from, and show that I care early on, I think goes a long way.

5:27 Scott Ingram: Another way that I see a lot of sales professionals build trust throughout the sales cycle is with video using Vidyard. It's an incredible way to humanize your asynchronous interactions. By looking into the camera as you record, your prospect will feel like you're looking them in the eye. The best part is you can get Vidyard for free and also know when people have watched your videos. Get started today at top1.fm/vidyard. Let's contextualize this a little bit, and I'm going to go a bit broader and have you talk about not just your current role, but maybe some of the work that you did at Jobvite. I know you moved very quickly from SMB sales to now enterprise sales. So, talk about that adventure and kind of what you're up to right now.

6:12 Jenna Phillips: Yeah. So I was a part of Canvas originally, which was a text-based interviewing software. So we were a startup. I was our first SDR, first outbound function at all. I was able to, you know, gain a lot of success in that role quickly. We added a VP of sales and 3 SDRs promoted me to AE and added 2 other AEs. And then we were pretty quickly acquired by Jobvite. And so got to move into an SMB. Well, at Canvas, I was an AE of all kinds. So I was selling to, you know, SMB to enterprise, but that was my first role as an AE. When we merged with Jobvite, I became an SMB AE there and quickly became a mid-market AE and now have moved into the role of enterprise AE over at Authenticx. But before leaving Jobvite, I was able to achieve over 100% to goal every quarter and was number 1 AE besides ramping AEs every, every quarter, as well as hit quota to attend President's Club during the pandemic as the only AE that was able to, to hit, hit goal and attend President's Club.

7:27 Scott Ingram: That's awesome. That's, that's quite a, quite a story and we'll, we'll dig into it more, but I would love to hear how did it start? What, what's the origin story? How did you get into sales in the first place?

7:37 Jenna Phillips: Yeah, great question. So I'll go really way back to a story that I don't think I can leave out when talking about sales success for me is I grew up on, you know, in a large neighborhood in Tucson, Arizona. And my best friend on the street was named Jordan Lazzardi. She's also in sales now, I'll say. And her and I, you know, we didn't just play games like normal kids do. We weren't just sitting playing, you know, board games and dolls. We were making little businesses and one of them was called All Occasions And we basically were just like, we'll do anything for anyone whenever they need it. So we would walk around our neighborhood, which probably would not fly today, but we would walk around our neighborhood and ask, you know, who needed, you know, weeds picked or, you know, any kind of task we could achieve for them. We even, I think our most successful endeavor is we had a face painting kit and we would go door to door to the houses that had kids and ask if we could paint their kids' faces for money. And like, people did it. We really, we made decent money for, you know, 8-year-olds or 5-year-olds even. And we just loved it, thought it was really fun. So Jordan's now killing it at a sales career in UPS. But that is like an example of I've always been selling and everyone who knows me knows that I am always selling something, whether it's you know, my friends coming over or, you know, as a Young Life leader and you're pitching, you know, you're pitching a relationship with Christ in that basically. Right. And so it's been always in my life. When I graduated college, I joined the Orr Fellowship, which if you're local to Indy, it's a leadership development program, placed me at a company that's called the Federal Home Loan Bank. It was a super corporate kind of environment. And I was in marketing roles, primarily marketing, a little bit of recruiting, different project-based roles. And I really liked that. But because of the Orr Fellowship, I got the opportunity to lead the Orr Fellowship recruiting team. So there was about 90 people. Carly Montgomery was actually on that team. She was on one of… she was on my leadership team. And, you know, we basically were selling the Orr Fellowship program. We were recruiting people, but we were selling the ORE Fellows on joining the Orr Fellowship. And I got such a thrill from that role. I loved it. And so when the fellowship was about to be done, I kind of got together my, if you will, internal board of directors or my personal board of directors and asked for advice. But I brought a few roles to the table and asked their thoughts on it. And multiple were actually recruiting because I got such excitement from that recruiting role and so much fulfillment from it. But multiple of those board of directors, and particularly one, one in particular said, you can always go back to recruiting after you go to sales, but you can't necessarily go to sales later after recruiting. He was like, sales is the foundation for a business. It touches every part of the business. And ultimately for me, leadership is the end goal. And You know, those board of directors shared with me how in sales you touch so much of the business that you prep yourself to be a leader one day because you already know the different elements that need to be involved in making the business run. So with that, I found Canvas that was selling recruiting software and it felt like the kind of blend of the two that I was looking for.

11:16 Scott Ingram: That's awesome. It sounds like, I mean, you're on a pretty clear trajectory. You've mostly worked with more kind of startup-scale organizations. I mean, Jobvite wasn't a huge, huge organization. What, what precipitated the transition from Jobvite to Authenticx?

11:30 Jenna Phillips: Yeah. Yeah, I definitely, you know, I like trust at the beginning. You said another thing that's been a theme in my life that I didn't anticipate to be a theme in my life was newness, like being a part of new things. I moved a lot as a kid growing up. And I was always, you know, always the new kid. And then, you know, in college, I was a part of founding a sorority and loved that. And I could give endless examples that just I find myself in things that are new, places where, you know, the place is new. And Canvas, it was really the text-based interviewing, the recruiting piece paired with sales that got me excited at first. But once I was there, I realized how much I loved being a part of a place where, you know, there's not process built, there's not rulebook, there's not a playbook, and we have to figure that out and play that out. And there's a lot of challenges that come with it, but I love it. And so, as you know, we were acquired by Jobvite and Jobvite kept growing. I mean, 4 companies were a part of that acquisition, you know, I was selling a product that everyone has, right? It's, it's a product everyone has to have an applicant tracking system if you're a recruiter. So it's a replacement sale, right? So you're, you're calling and, and someone has this technology in some capacity and you want them to change to this other capacity, which, you know, that has its challenge, right? Because you're running against about 40 competitors sometimes, right? Maybe at minimum 5 competitors, which is a hard sale, but it wasn't as hard as selling something that someone has never heard of. And I found myself getting bored a little bit. I just, I was bored in that, you know, I had, I was pushing myself as far as I could, but was, you know, was still able to achieve the success I could. And probably could have done more because at the end I was relaxing a little too much. And for me, a lot of my close friends know this analogy. I feel like my career, I always envision myself on a treadmill. And if the incline on the treadmill doesn't feel like it's high enough, meaning it's not hard enough, like, right, it's not challenging me and stretching me and making me better tomorrow. Then I get itchy. I need to be where there's a lot more challenges around me. So when Authenticx reached out and, you know, basically I view this as a rocket ship, just as Canvas was, right? And I think if you're looking at joining a sales team as a first salesperson, there's quite a few things to look for. One being, and Aman Brar, who was the founder of Canvas, is who shared this originally. It's looking for really good people to work for, really great leaders to work for that you believe in. A really amazing product that you believe in, that you, you think they have found something that is needed. And then that, you know, look for the rocket ship, right? Look for you're solving really good problems that people need, that people need the problems that you're solving. And if you can find that, it's really hard to find all of those together and go to it. So I felt like I had that at Canvas and I'm really glad I got to be a part of the scaling of the Jobvite team and the blending of the 4 companies. But then I found this rocket ship in Authenticx and, and couldn't pass it up.

15:07 Scott Ingram: Another company I've found that has this same combination of traits that Jenna just described is Revenue Grid. They've got great leaders, a great product, and they're solving really good problems that people need. Their revenue intelligence platform is all about shifting your CRM from view mode to do mode. Do this for me. Click over to top1.fm/revenuegrid and check them out today. It's totally okay if you need to pause the episode to do it. So, you know, we call the show Sales Success Stories, and I feel like we should probably tell the story of a sale. What's your favorite sales story?

15:44 Jenna Phillips: Yes. So my favorite sales story is… I've gone between 2 deciding on this, and I think, I think I'll start with one. So Yeah. Okay. My favorite sales story. And it's really my favorite in part because it was my favorite childhood restaurant and I got to sell to it. So I moved around a lot, right? Moved around, lived in many different places, but growing up in Tucson, Arizona, a company called E.G.'s, what is, it's just, it's Tucson. It's the culture of Tucson. Everyone in Tucson knows it. If they don't, They did not live in Tucson. And so when that came in actually as an inbound demo request, I just almost lost my mind. And why it's my favorite sales story is I was so invested in that sale and, and they knew it. This, the, the people on the other end, the customers knew it. But because of that, every move was so thought out and every engagement with the prospect was so thought out. And I was able to take our product and bring it to life in such a way for in their world, because I knew their world so well to an almost bizarre level. And so we, you know, were able to, for the size of company that they were, we were able to bring to them a big leap in the product capabilities compared to what they had before, because, you know, they were able to sell it to their leadership so well because of the pain and the story I was able to tell with our product and their world to the T. So we actually, like, we were shut out by their leadership, their CFO for a little while. And then we were able to bring it back to life by, again, just like really honing in on the pain that they were experiencing. Right. I mean, recruiting in America is really hard right now, but especially for restaurants. And so telling that story, but telling it in a way that showcased who they are and their brand and what they're trying to do and where they're trying to go. And for me, it was a reminder of, wow, I need to get to this level. Of understanding of someone's business. If I could do this on every deal, then, then I would never lose, right? And I just had this, this background knowledge that I need to be searching for and prepping for in future deals.

18:21 Scott Ingram: What a great, what a great lesson, right? And I mean, it comes across, right? If you get super passionate, not just about your own product and your own solution, but about their business and what you're trying to solve for them, right?

18:33 Jenna Phillips: Yes, understanding the customer's world. The one move or the one story that really resonates with me on that, understanding the customer so well and how that can be a game changer, is I'll kind of take out some of the details of this one, but in account management, so my new role has a little bit of account management in it, which is new to me, but I got the opportunity to really know this customer really well because of that. And this customer had, this customer had to pause all strategic initiatives because of, you know, something going on in the world that was completely out of their control. So from, from the CEO, they said all strategic initiatives paused and they viewed us as a strategic initiative. And so they had to pause their relationship with us. And I think earlier in my career, I would have been like, oh, this is terrible. They have to pause all strategic initiatives. What are we going to do? But I paused and said, okay, what's causing them to view us as a strategic initiative? And how do we become not a strategic initiative? And the nice part is, again, going back to that trust I built with my clients, I knew that my client, my champion at the company, did not want to stop working with us. Like we were adding value to them that was very helpful and they did not want to stop, but they didn't know what to say to their C-suite, right? Who was telling them they had to pause strategic initiatives. So my CEO and I came up with how are they not, how are we not a strategic initiative? And with that, we, you know, we turned around what we were doing, what the current, you know, sell to them was, or the current proposal that they were working with us on, and made what was going on in the world… we dug into what was going on in the world, and we showed how we made their lives easier with what was going on in the world around them. And so because of that, we not only saved the deal, but we grew the deal. And You know, our, our, my CEO, COO said it's the top 5 sales move he's ever seen. And it was so simple in just stopping and saying, okay, this is why they're saying they have to pause. These 2 words, strategic initiative. And how do we get out of that?

21:01 Scott Ingram: That's so funny. Cause I feel like most of the time we're trying to become a strategic initiative and here you're like, no, no, no, we're not that. We're something else. That's so great. Yes.

21:11 Jenna Phillips: Yes. We're emergency response kind of, right? They were in emergency response. So we need to be emergency response.

21:16 Scott Ingram: That's awesome. That's awesome. Well, Jenna, you have had a lot of very consistent success. You've ridden a couple of rocket ships. What are you most proud of?

21:25 Jenna Phillips: Yeah. You shared this question. I've really thought hard about that. And I, you know, you get in the, when you're moving as quickly as I've been fortunate enough to move. You get excited about the little wins and then, you know, and then move on. And I think for me, I have to say it's just the ride I've been able to go on as quickly as I've been able to go on. I think, you know, getting the opportunity with Canvas and seeing that as the rocket ship it was, getting in early and being able to take in all that I learned and use that to grow quickly, to get to where I am, to go from SMB to enterprise in 2 years is probably what I'm most proud of. The quotas and the numbers and those things in between obviously are really exciting, but that is what I'm most proud of.

22:19 Scott Ingram: It sounds like there's a part of that that is right place, right time. And in this last move, for sure, you've been intentional about it. Were you, were you that intentional with the first step with, with Canvas, or did that just kind of work out that way and then you recognized it?

22:37 Jenna Phillips: Yeah. So I keep mentioning Carly now because Carly will speak to this a lot with me. Right place, right time. I don't think it exists. I have been called lucky multiple times in my life and, and I don't believe luck exists. I think it's when preparedness meets opportunity. And that's what people see as lucky. So I'm always trying to look 10 steps ahead. So with Canvas, you know, there were multiple other companies kind of at that time that I was looking at that are, you know, a part of the story that I didn't mention maybe, but I was really looking at each of these companies with a fine-tooth comb. I mean, with Canvas, It was a lot of it was about the leadership, but also the product and how mind-blowing it was. I don't think I asked nearly enough questions of the Canvas leadership than I did of this leadership, which luckily that Canvas was amazing. And I got maybe, okay, maybe it is a little bit of luck. I asked as many questions as I could have at that time. Now I ask a lot more when I join a startup just from what I learned there and what Canvas did well. And I've seen so many of my peers go to startups that fail quickly. And so, I mean, my new boss and leadership, I mean, they were… I put them through the wringer in the interview process. They… we still joke about it today because I came back with about 15 questions in the interview process, mostly around the finances of a startup. So when I'm going to join a startup, I am checking, you know, their runway. I'm checking, you know, I'm checking, of course, obviously the revenue, but a lot of details that go into that. I've got about 15 questions I won't bore you with right now that all of them are very important to me to make sure the company is stable first off. But then, you know, was there ever a sales team before? Like, how have you tried to sell? Like, how did you know who failed before and why? And okay, so you're breaking a new technology. Why has no one ever done that before? So I'm really interrogating them to make sure before I jump to a startup. You know, I love that.

25:00 Scott Ingram: And maybe you can send me those questions and then we'll incorporate them into the show notes. If you go to top1.fm/this episode number or top1.fm/Jenna-Phillips, we'll have it all there. I am, I talk about this all the time and how important doing your own due diligence and asking these questions and really trying to figure out, and you've, you've honed into so many pieces, right? Really understanding the leadership. The leadership is so, so key, right? How are they thinking? They really defined the culture, especially in a startup, right? Their mindset, the way they're thinking, the way they treat people, the way they treat customers, all of those things carry through. And the financial piece is so important as well. And the way I always think about it is if you're joining, say, a 50-person organization, you represent 2% of that company. So, you know, maybe that's how they're thinking about you. Now, not explicitly. They're like, oh, Jenna's just 2%. But for you, this is going to represent 100% of your professional life. So it's way more important to you than it is to the company. And I think because of that, it's incumbent upon us to make sure that we're putting ourselves in those right positions and, and we're taking our time. And I think, I think it says a lot when you take this amount of care, and maybe you can speak to this, you know, how that's received when like, no, no, no, no, this is my process. Like, I'll be asking the questions here to make sure that this is a really good fit for you. Yeah.

26:33 Jenna Phillips: I mean, I think in an interview, I mean, in an interview process, It says a lot about who you are because, you know, when I accepted at Authenticx, my boss said, I feel like we just got, you know, the top pick and the top pick in, you know, the NFL draft. And I think the reason he said that is, and is because I made it clear that, I mean, I didn't want to leave Jobvite. I wasn't looking to leave, which I told my leadership there many times when I left. I really wasn't like, I hadn't applied to any jobs. I hadn't looked at any jobs. Like they reached out to me. And I was just intrigued enough about the product to take the first call, but I was very skeptical and I was asking them a ton of questions, like I said. And, and so I think, you know, it showcases the confidence that you have and the skills that you have built and like you're showing, I don't need to go anywhere. I'm not trying to go anywhere. Like, I'm only going to go if this is going to be a really good fit. And I think at the end of the day, especially in the startup world, like you said, 2%, but 2% in a startup means a lot, right? That's a big deal. So they want to know that you're the right fit too, and that you're not going to leave quickly or, you know, that you're not going to be invested. So it shows that you're really invested and that you are not going to come unless it's the right fit mutually. And I think it earns respect and teams like it. Obviously everything else you do in the interview process has to be going well to go into that kind of question mode, but, you know, having that confidence to do so, I think says a lot.

28:11 Scott Ingram: Yeah. So we talked about what you're proud of. What's the flip side? What do you find to be the most challenging part of sales?

28:17 Jenna Phillips: What do you struggle with? Yeah. Taking back to when I first moved from SDR to AE, there's a lot of podcasts and speakers out there that say, you know, you're looking for the no as an SDR, right? You're trying to get them to the no quickest. But the reality is when you're on a cold call, you're trying to get them to the yes. Like, yeah, if they're gonna say no, you want them to say it, but you wanna get to the yes because you're just trying to get the meeting booked and move on with your day. And so if you get the yes, you're holding onto the yes and moving on, right? So I think the biggest part for me in transitioning was realizing like getting to the yes is not the end in any stage of the process, right? So you're in negotiations and they say, yeah, that looks good. Okay, what, what else? Like, what else do you need to ask? So I have had rosy-colored glasses at many times. I still have rosy-colored glasses. I think it is way better now than it was when I started. And I really work on it. And all of the leaders I've had in the past have helped me work on that a lot. But I mean, if you know the StrengthsFinder test, one of my top strengths is positivity. And I think it's helpful in sales in some, but it can be a barrier. And it actually has moved down since I've been in sales. But, you know, I have to check myself and say, do they just, you know, love the product? But do they have the ability to buy the product? Do they have know, the right ability in the, in the company? Do they have the right people's ears? Have they bought before and do they know how to buy? There's a lot of different things I need to go through to make sure that they actually can buy. And that's one example, right? There's a lot of different examples of where they're telling you one thing and needing to pause and say, okay, what's below that versus just the positivity. And I think I struggled with this at the beginning the most because one of the things I think is my strength is when I'm in a deal, I am like all believing it's going to close so much that I'm shedding that onto the prospect. And I work with the prospect to be kind of their cheerleader and be excited for them and help them share the excitement they have for the product internally. But then when you're coming back to your team and, you know, taking a sit back and like, okay, what's my forecast? What am I closing this, this month and this year? You have to take those glasses off and realize, you know, look for what, what's the real facts on where we are with the deal. Yeah.

30:50 Scott Ingram: It's almost adopting healthy paranoia, right? Yes. Yes.

30:56 Jenna Phillips: The skepticism, right? I, yeah.

30:58 Scott Ingram: Being skeptical all the time. Yeah. Well, let's talk about routines. This is one of my personal favorite areas to really dig into. And the way I like to ask this question is, I'd love to hear what a day in the life kind of looks like. And let's start with your alarm clock goes off. What time did that happen? And I want the blow-by-blow until your head hits the pillow.

31:21 Jenna Phillips: Yeah. So I am not the most routine person and this is something that, you know, I think I definitely can work on and probably would take me to the next level. Sales leaders in the past think I'm crazy. My dad has always told me like, If you don't make your bed, there's no way in hell you can be successful. I don't believe that. I just don't. It's not in my nature necessarily. Now, I will say when my alarm goes off now, I go to the gym in the morning, which is not something I did a year ago, probably. And I will say it does make a big difference because I've never been diagnosed, but many people in my family have. With ADD, ADHD, I just, I have focus issues like nobody's business, which I think is part of the reason I like the AE role. Like there's so much going on, right? So working out in the morning helps me focus a lot. I notice on the days when I don't that my focus throughout the day is not nearly as strong. So that's the first thing. And then obviously then I'm getting ready for the day. I am one like I do my full hair and full makeup almost every day because even in the work from home, you know, I've been working from home for about 2 years now and not every day do I have customer calls, right? But I feel like it puts me in the right mindset for the day and gets me ready. And then, you know, I'm looking at… we use HubSpot. So I'm like from right to left, right? Because the deals are at the left side is the top of the funnel and the right side is the end of the funnel. So whatever that is in your world, right? Top of funnel is left. So I'm always looking like from, from the right, from the bottom of the funnel, the deals that are closest to close, what needs to be done with them? And I'm making my priority list for the day based on the deals that are closest to closing. Now, I'm not saying like those are where I'm focusing everything, but like, is there anything that needs to be done for them. If there's not, fine. But if there is, that's going to the top of my priority list. And then I'm moving to the left and making that list in priority order of what needs to happen. And I also, I'm now in the role where it's all enterprise, right? But at Canvas and then also at Jobvite, I kept some Canvas deals at points. And then also just the SMB was, had a wide range of quick-moving deals and then deals that are more of your like strategic game-changing, year-changing deals. And so I will break those kinds of deals up, right? So you're, if you're in one of those SMB mid-market, right? Do you have deals that can close quickly, that can close in a couple weeks or a month or 2 and lumping those together and then lumping together your strategic deals that need more care and more attention. And because of that, I'm thinking, thinking about those deals very differently. And I think you need to separate that to think differently in, okay, on my, my quick-paced deals, is there anything that I can do today that's going to move them so that I can get them off my plate? Because I want to close these deals as fast as I can. And if there's anything that I can do for them today that will, you know, help them close tomorrow or this week versus the next week, I'm going to do that, but I am not going to spend a lot of time on it. So I'm going to lump those deals together and I'm going to chug through, like, I want to give myself 30 minutes and I'm going to chug through all of the action items for those little deals quickly. And then my more like game-changing strategic deals that might not be closing quickly, like, is there anything I can do that can move the needle in a big way? And I'm prioritizing that. But, you know, a lot of times the things that need to happen for those kinds of deals maybe take more brainpower, more thought, more, you know, you're, you're actually having to sit down and write something out that you want to be very thoughtful on. And so, you know, I'll, I'll chunk that kind of task together as well.

35:32 Scott Ingram: That's a really interesting process. I like that breakdown. In a perfect world, I mean, what's the right mix for you? What percentage maybe of fast-moving deals are you working versus those bigger, more strategic game-changing deals?

35:43 Jenna Phillips: Yeah. Now I'm in the world where I have pretty much all enterprise. So I'm figuring out what that, that mix is here. But in my previous world, I guess it carries over both. I'm always looking at my number that I'm expected to close for the year as a task item. Like I don't view it as a goal. And maybe that's kind of that, what do I believe that is game-changing that I think maybe other reps don't believe is like, I view that as a task. That is in my job description to do. And that is what I like committed to the company to do pretty much. I don't view it as like this goal that I hope I get to goal. I, you know, I'm trying my best to get to goal. Like I view it as like, that's what I have to do. And so I'm looking at my big deals and seeing, you know, how many of those I expect to close when and et cetera. Right. And then looking at the gap And, you know, I'm typically, I'm looking at like 3x-ing the gap with deals, right? And in terms of dollar amounts. So oftentimes I'm bringing in, you know, those little ones to fill in those gaps. And so my breakdown specifically, I think it really varies based on your, your deal cycle and how long that's going to take. Right. But depending on the time of the year, I will say I'm, you know, working with my SDR and my own prospecting to think of like, What size deals should we be prospecting right now for the goal, right? So like at the start of like now and at the start of the year, you know, I really want to be targeting those mega deals, right? Like I really want to be targeting those big target accounts, the largest enterprise, right? And then shortly after that, then I want to start getting into like the quicker deals because I want to make sure I'm getting in those big deals with plenty of time. In the year. And then, right, you know, where maybe a month ago where something could have come in and still close this year, I'm telling my SDR and myself to only try and bring in those little deals because maybe they'll close by the end of the year. Right. Yeah.

37:51 Scott Ingram: Let's talk a little bit more about kind of your goal setting process and your mindset around that. How are you thinking through that? Yeah.

37:58 Jenna Phillips: Now, when I am at my best, I am looking at, okay, looking at that number, I'm taking in any data points I have. So my close rate, right? So currently I'm in a new role. I don't have my close rate here. I don't know it yet. So I'm taking in my previous close rate and then other people's close rate at, you know, well, there's not other people at this current company, our CEO's close rate here. And I'm kind of guessing taking those and deciding what I think my close rate is here. And then looking at the timing of the year, right? And the length, how long it takes for each deal to close. And then I'm breaking that into monthly goals, right? And even weekly goals of, okay, so this is, you know, if let's say $1 million is what I need to close for the year, if I think my close rate is about 30%, then I need $3 million in my pipeline. And when do I need it? Like looking at what I have closing when and when do I really need to be bringing in deals and when do I want them closing, right? So that decides if I need bigger deals or smaller deals. I will say, you know, like this time of year I can get really bad about thinking about that stuff still and taking that stuff in because I'm focused on closing, right? And so I think This is the time of year where we have the opportunity to, okay, obviously what can we close now? What needs to close now? But then we're about to be in the time where we can step back and look at these kind of numbers and be more strategic. I am not your process detail-oriented AE by any stretch of the imagination, but the one thing I do really care about is those kind of goal numbers. And I care about them in part because I, most of the time have had an SDR and I'm about to have 2 that are specifically to my territory. And for them and myself to see like why the prospecting matters so much at the front of the funnel or why moving a deal stage to stage matters so much, it helps me stay grounded and it helps my SDR stay grounded in, okay, like I'm not just calling to call, I'm calling because like This is what we have promised the company we will close. I know we don't actually promise it, but I like to tell myself I promised. And this is what needs to happen to get us there. And that's why X activity I'm doing right now matters. So it keeps, it keeps the why behind what we're doing every day.

40:30 Scott Ingram: Yeah. Talk a little bit about that SDR, those SDR relationships, and also the piece of what are you taking on yourself and how do you think about that?

40:39 Jenna Phillips: Yeah, I am very much… I could get really passionate about this. I'm very passionate about the fact that if we are going to have SDRs where their full-time job is to prospect, right? Like every single day, their job is to prospect for 5 days a week. My job is to prospect and close deals every week. So the time I have to prospect is just substantially less than what the SDR does. And if I am setting more meetings than the SDR, I believe, and like my boss will roll his eyes at this. I've had like a lot of people will, but I believe that's wrong. Like I think I'm failing my SDR if I'm booking more meetings than they are, because I think that an hour spent developing your SDR is a bigger investment into your week than an hour spent prospecting. And I think if we invest in the relationship with our SDRs, it benefits us tenfold. And like, I'm very proud of my SDR at Jobvite. She was like a nurse before. She was a, she was an autism specialist before. And then she came in and had never been an SDR before. And we had one SDR who was just absolutely crushing it, but she went all the way up to being number 2. And in 2 quarters. And so the reason behind my investing in the SDRs is if you invest in your SDR, they're going to produce so much more for you and it maximizes the 2 of your time in a week. So I'm still taking prospecting on myself, but I'm always going to, like, if I have 30 minutes and they're free, like I want to be working on their talk track and working on their emails with them until hopefully, right, we get to the point where they're, you know, they're confident and they're going and maybe they don't need as much of that time. And then I'm investing, you know, in myself and my prospecting. But when they're newer, when they're still learning, like I'm going to do that all day long before I do my own prospecting.

42:48 Scott Ingram: What's typical in terms of that breakdown? How much time are you spending prospecting each week and how much time are you spending with your SDRs?

42:55 Jenna Phillips: Yeah, each week with my SDR, currently I'm spending probably 2 to 3 hours a week with them. 2 to 3 like formal hours, but probably more like 4 hours or so with them every week. And then I'm, yeah, and then I'm spending maybe about that prospecting. So it's an area for me Especially depending on the time of the year, prospecting is not something that I am best at forcing myself to do every day. And it's something that I still need to work on, but I'm also in the enterprise space realizing like I need to do it more, but much more strategic, right? Like sending some time, sending out bulk emails to leaders is not going to work in this kind of space. And so spending time being much more strategic about who I'm reaching out to. Yeah.

43:50 Scott Ingram: Awesome. And just put that in the context of what is a kind of regular work week for you? Is that a 40-hour thing? Is that a 50-hour thing?

43:57 Jenna Phillips: Is that, what is that? Yeah, I'm more of a probably 50 to 60 hour. I'm also, and this is something my new boss had to get used to, to, he's, he's pretty structured and I've had, you know, bosses that range on all spectrums of that. I'm the kind of person that like, if I have to write a proposal or, you know, build something out for a prospect, I do that best late night. So I will work, you know, from 8 to 5, you know, talking to prospects, writing email or reaching out, sending emails, making calls, all those kinds of things. And then I'll pick my computer back up again at 8 or 9 and, you know, make a proposal until 11 or 12, you know, at night. And that's very common for me. And so I, yeah, I definitely in the past have been known, well, always have been known as, as an AE that's putting in more hours than the average AE.

44:57 Scott Ingram: Gotcha. Perfect. And then what does your kind of toolset look like? What are the tools and apps that you can't live without?

45:03 Jenna Phillips: Yeah, I love Gong. I could not live without Gong. Number one reason for that is I, again, that kind of distraction level. If I am able to be so present in a call that I am listening fully to the prospect, able to, you know, think about what question I want to ask next, and I don't have to take notes, that is so huge for me because then I can go back to Gong. I can look at the recording. I can look at the notes. And, you know, it helps me in multiple ways, right? Because I end up having to go back to the call. To get notes, but then I hear what they said twice. So I listen to what they said again. I'm listening to pretty much every call I do again afterwards, if not 2 times afterwards. Right. And it's game-changing. Like, I'm nervous about when we go more back, you know, back in person and not having that necessarily because I just like to be a present active listener. And having to take notes doesn't enable that well, right? But then if I'm not taking notes, listening, you know, you're missing those key points. So that is really big for me. I also, you know, we use HubSpot and we had Salesforce at Jobvite. I almost, that was a point that I pushed on before I started. I really wanted us to have Salesforce, but I will say Gong has Their deal flow is probably more helpful than Salesforce or HubSpot when it comes to like checking yourself on your deals and what people need. Because being able to look at my deals and see, wow, that doesn't have a whole lot of activity on it. I need to think of some way to reengage this activity or move this activity along. Or looking at, you know, it actually gives you, hey, here's action items that you need to take. Like, you met with this person yesterday, send them an email. You met with this person, send them an email. And I actually got to sit in on recently a Gong potential product list for a new product they're bringing out that will make them even more kind of CRM-like. So I just honestly, HubSpot and Salesforce, neither of them have that kind of what I would think a CRM is, where it's like, here's all of your deals in front of you with kind of an easy way to take in all of the actions happening on them. So that's my one tool that I really could write home about.

47:37 Scott Ingram: I really can't manage a sponsor mention any better than that. To check out Gong for yourself, just click over to top1.fm/gong and you can tell them that Jenna made you do it. Any other tools that are worth shouting out?

47:50 Jenna Phillips: Yeah, I know I got so passionate about that one. I need to stop and think about other ones. I mean, ZoomInfo is obviously really helpful to find people, but I also, I think Sales Navigator, obviously ZoomInfo then takes the data out of Sales Navigator and that's helpful. But if you're especially like, if you're an enterprise, any SDR team or that's prospecting, that is pulling their list straight out of ZoomInfo is missing a ton of people. Like going into Sales Navigator, especially, I'm a big believer in, okay, I just met with, you know, this prospect. They were exactly who I want to meet with. Then you scroll to the bottom of that list on Sales Navigator. You go to that prospect on Sales Navigator, you scroll down and it shows you people like them. And I have found that to help me find some gold because, you know, titles are, you know, ever so different everywhere. And if you can find those people that have that really similar or really similar combination of titles and skills and whatnot, it goes a long way, especially the role I'm in now. We can sell to any title path basically. And so that's really helpful to find the specific people that will be Good champions. Nice.

49:10 Scott Ingram: And then what about your information diet? What are you reading, listening to, and watching? And when does that happen? Yeah.

49:16 Jenna Phillips: So I'm rereading The Challenger Sale with my SDR right now. So I've read it before. She hasn't. So we're reading, you know, about 30 pages a week and then talking about it in our Monday one-on-ones. And that's been really helpful. I love The Challenger Sale. I think the meaning from it, the lessons I've learned from it. Have been really helpful. And so going back and doing that again with her is big. I'm actually working on my MBA right now. And so a lot of my information diet and, and what I'm taking in is that currently, which has been really helpful. I think, you know, salespeople getting an MBA is not super common, but it's helpful for me in a multitude of ways, right? It's like I just had to take accounting and finance classes, et cetera. And we're taking it, you know, I'm doing the Executive MBA program at Purdue. And so the element of the Executive MBA program I think is really helpful for a salesperson because we're taking all of these classes from a management level. You know, when we're taking accounting, we're taking like, what does the, you know, chief accounting officer, the CFO care about? What's important to them? And, you know, same when we're in finance or we're in, you know, supply chain. And I think it helps with what does this CFO that's my gatekeeper, like that's keeping me from getting this deal across the line, what do they care about most and how do I speak to them? And so I think right now I'm spending a lot of time not necessarily on sales skills and their typical intake of sales content, but on learning the rest of businesses, which really helps me with selling. But a couple of salespeople, I mean, so I took Jeb Blount, he's local to here. I took his sales class at the beginning of my sales career and that was huge. I think like, I don't even think I realized how much what I do now, I'm like, I go back to what I learned from that class. I also am big, like I am a big learner from people versus reading. So when I first started at Canvas, you know, I was again the first salesperson. So if you are thinking of going down that route of going to a startup, being a first salesperson, key thing is like find your community because you won't have peers to bounce ideas off of. So I will build, and I've had multiple different groups like this at different stages where I'll find people like me in the city. I guess it can be virtually too now, but I'll find people that are in similar roles and get a group together and meet regularly where you're just coming to the table with like, hey, this is a problem I'm dealing with. This is a roadblock I'm hitting. What are… what's going on in your world? And that has been helpful. I also did Girls Club, which is a leadership development program for women in sales who want to be in leadership. And so the goal is to help you get to that first leadership role. And the content in there was really helpful, one from a sales learning perspective, but then also sales leadership. And like I said, that's a goal for me in the near future. And so prepping myself there, right? Thinking ahead. Like I said, that 10 steps ahead, I'm always like, like, that's where I want to be. So I'm reading more content around sales leadership right now. But in that, I also found another one of those groups of people, right? There's 2 girls in that program who are both in startups and are, you know, one of the early salespeople. And so we talk regularly. We've got to, you know, we'll Slack each other and say, okay, this is going on, I need help, or we'll, you know, get together virtually and have gotten… neither of them live in Indy, but we've gotten to even get together in person. And that's huge. The other person I follow is Ian Koniak, which he has been big for me in enterprise sales. Like, right. Like that's the, If I am reading something sales-specific right now, it's enterprise, and I want to be taking in that enterprise content.

53:13 Scott Ingram: Brilliant. Tons of great callouts there. I haven't talked to Jim Brown in forever. I know he's a big indie guy, so I'll have to use that as a prompt to reach out and reconnect. But again, we'll have links to all this stuff at top1.fm/theepisode number or Jenna-Phillips. Jenny, you talked about Challenger, you kind of alluded to some Sandler-type items. You mentioned Jim Brown and some of these other resources. Do you subscribe to a particular sales philosophy?

53:43 Jenna Phillips: Yeah. I'm also in Lucian right now. Lucian is also local. So I have a sales trainer there, Brian Kavicky. So that is Sandler-based. I've done, yeah, I've done them all. I like them all. I do not succumb to one strategy specifically. I think I do use a lot of Challenger and really how I use Challenger is checking myself because I think naturally I'm a relationship seller in my most natural state, but allowing myself to think through that and look and kind of put the Challenger, you know, put myself in the mirror with the Challenger book and the thought there. I think the Challenger sale comes very natural to me too. And so And just checking myself, like, am I leaning too relationship salesy today? Do I want to adapt that? But then, yeah, I mean, I take Lucian locally and so, you know, have a trainer with that, with Brian Kavicky. And so, you know, that's Sandler, Sandler rules, and I'll bring that into it. But then also Miller Heiman. I've been Miller Heiman trained and that's one I don't think is as commonly talked about in the software world. But it's really big for enterprise. And so my largest deals, and it's great to do them with all of your deals even, is there's a blue sheet with Miller Heiman that my dad has always, has been in sales too. And I'll be talking to him about a deal and he'd be like, well, where's your blue sheet? Do you have a blue sheet? And like, he can't even talk about a deal without having a blue sheet in front of him. So it is helpful though. It basically You know, has, you have to think about a multitude of different components of the deal and think about, are there red flags here? Are there red flags here? It's bringing out any issues that may be happening in the deal on your own early on so that you're focusing in on them and you're attacking them. And I think that's really helpful, but like in the day-to-day of selling, I think more the Sandler or Challenger are helpful. So kind of bring a combo together to make my own style.

55:51 Scott Ingram: Yeah. Well, that really is the most common answer and Right. You know, the most common references are always Challenger and Sandler as well. You know, it's interesting you mentioned kind of the relationship piece in Sandler because, or in Challenger, because I feel like, I mean, it's kind of part of the way that Challenger challenged us, right? And I think probably overly maligning the relationship sales piece, because it's not like if you're a Challenger, relationships don't matter. Or they're not important. And my other read around it, I mean, that book has been around for a while. I think when it came out, there was still a lot of this. I think the relationship people they were going after was the, my job is just to schmooze. Like, I'm gonna take you out to steak dinners, we're gonna golf, we're gonna do all this stuff, and I'm gonna rely way too heavily on that. To the exclusion of I actually bring value to your business, right? I, I think that's kind of my read on that. I think it gets taken a little bit too far and it's like, hey, look, relationships are still important. Let's, let's not, you know, move too far away from that. And, and I certainly relate to that. I am very, very relationship-centric in the way that I sell, but not the let's just go to dinner and you'll do business with me because I buy you gifts.

57:12 Jenna Phillips: Yes, such a good point. And I think also, I think women tend to, you know, you tend to navigate to the relationship seller first because it's kind of how society shapes us to be. And like, honestly, I think probably, you know, if like gender didn't exist and gender stereotypes, like maybe challenger would be my default, but there's, you know, society pressure that kind of put me more in that relationship selling. Mentality that was just, yeah, I love people and positivity and being around people, all that kind of stuff. But I totally agree with you. And I think kind of going back to the beginning of our conversation, I talked about how, you know, I build trust quick with prospects. And I think my style, what I love to do is it's kind of like relationship building upfront where you're building that trust. And then it gives you the ability to move into the challenger sale. So it's like a combo of the two that is my sweet spot. So favorite story, maybe more than my other two, another favorite sales story that I think I really got to do this to the best that I could was, you know, this deal at Jobvite. You know, first off, the woman and I just connected right away who would be You know, the champion. We really bonded from the beginning, but it wasn't like we weren't bonding about, you know, again, like family and that kind of stuff. It was really about her world, her pain, understanding it and connecting with it. But then I actually flew out and this was like COVID had just dipped a little bit and gave me the ability to fly out there. And we didn't fly, you know, shortly after that, but I got to fly out, be in person with her. And her colleague, and we whiteboarded her entire process around the room. And like, for an applicant tracking system sale, that just rarely happens. But we, you know, Jobvite, the 4 companies merging together, brought this, you know, full suite of technology, right, for recruiters. And so she came to us wanting just the applicant tracking system, but the goal was, right, the whole suite. And by taking her process and we just She luckily had this room. I was like, do you have a room with a whiteboard? And she had a room that was basically the whole room was whiteboards. And we went around the room and wrote out from soup to nuts her recruiting process and wrote the current state first. Then we came back and looked at, okay, what's your goal state here though? Like, what are the gaps? What do you need to do and what's keeping you from being there today? And, you know, we did that for 45 minutes before we even talked about Jobvite. And then we, you know, I had my solution engineers there virtually and they came in and talked about the product. But when they were talking about the product, we were tying it to, you know, everything that we had just done around the room. And, you know, instead of doing a normal demo, I pulled up, okay, so for this part of your process, this gap you have, you know, my solution engineer is going to show you this one element I want you to see. And we just showed that one element then. And then we moved to the next. And this goes back to that other example of, right, really building a relationship with your, you know, solution engineers is maybe the first person that you really need to build that with because, you know, they had to sit on that call for like 2 hours and they also had to be ready for me to just say, okay, because of this one pain point, we're going to show this one piece of the product and then just be ready to go with it. But that is, I think, the perfect combination to me of That relationship up the front, it built the trust for me to come out there and see her and got us to the point of doing that Challenger Sale, right? Because we kind of beat out some of the other competitors because we had that relationship. But then we got in and did that full Challenger Sale and the relationship element, I took that throughout to close the deal. I actually left for Authenticx before I got to close this deal, but my colleague got to. But as I was, you know, moving it towards the end, you know, we had the relationship element that was present and that helped with, hey, can we get on the phone really quick? Like, hey, can we bring in this person? But we went back to that time in that, on that whiteboard consistently, and that and challenging their process and where they really were is what really closed the deal. But I think marrying the two is how you, you know, consistently win.

1:01:39 Scott Ingram: Yeah, it's so interesting. I think you called out the other issue that I have kind of personally with Challenger, and it goes back again to kind of the relationship piece. Because if you don't have some degree of relationship, and I think maybe the better word is trust, and what you opened with, if you don't have that degree of trust and you're really pushing back on somebody, you're just a jerk and that's not gonna work, right? So there's a lot of nuance in that, right? You can't just, and I've seen people just completely go off the rails with Challenger and I I think this is because they're lazy and they read the first 2 chapters and they think, oh, I just need to like get in people's face. And I'm like, this is not a-hole sales. Like that doesn't work. You know what I mean?

1:02:22 Jenna Phillips: Yes. Yes. And that's like with my SDR, the reason I think I'm having us read it now is, you know, the value I think Challenger has is, you know, you're for an SDR, you're cold calling and they say, oh, just send me some information. And it's like, Okay, well, every time I've sent someone information, you know, they just don't even see it. That's the end. And being able to push back in that moment, right? And I think it does a good job of showing the value in that and showing how that is helpful and that helps you win. But yeah, this is so agree with you on. Yeah, I don't like really any of those kind of tests or philosophies that go on such extremes because You have to have a combo.

1:03:05 Scott Ingram: Yeah. I mean, and that's it. And that is probably the biggest theme that I have heard having done, I don't know, 130 of these interviews is the people who are at the top of the game and are the best of the best have figured out to incorporate all of this stuff in their own style and their own way. Like, that's the secret. Like, if there's a secret to doing it and you came out of the gate with that stuff, right? Like, you have your very own distinct style. And you're just leaning into that and that works because it's you. Yes. Yes. Yeah.

1:03:38 Jenna Phillips: No, I, you know, my boss and I had to have a recent conversation. He comes out of the gate in meetings with, you know, really, really, really strong upfront contract and kind of like preamble into like what to expect, like what he needs out of the call. And it's not my style and I know I need an upfront contract. In my own way. Like, I need to, you know, I'm going to ask you some questions and, you know, at the end we're going to save some time to talk next steps. Like, I'm saying what's going to happen, but I'm never going to be the person who gets on the call and it's super formal and has this like structured thing I'm running through. Like, it's not my style. And I think the quicker you as a salesperson learn, like, okay, I'm going to observe a lot of salespeople and you should be constantly observing other salespeople to take them in, that in, but taking in the nuggets from each that are really like important, you think are important to them winning and then making it your own because you're trying to fit into somebody else's mold is going to exhaust you. Right? Like you have to figure out what gives you energy and the kind of style that gives you energy and can keep you moving in your process. Yeah, that's it.

1:04:50 Scott Ingram: I mean, and that's, that's kind of the point of the show. It's what you get out of Gong if you're listening to other people's calls. I think you have to kind of listen to this and just take pieces or try pieces that are relevant to you. I should also call out a resource. You mentioned Ian Koniak, who's been on the show. Jamal Reimer is another great one, just absolute huge enterprise sales star, just actually released his book called Mega Deal Secrets. If you go to top1.fm/enterprise, I've linked all of the enterprise sales-centric episodes. Same thing on the SDR side. So, if you go to top1.fm/sdr, you can get to those. So, if you're listening to this from one of those particular perspectives or you're interested in going down one of those paths, we've done a little bit of the work for you in that way. Jenna, let's talk about motivation for a minute. Like, what is it that motivates you? How do you think about motivation?

1:05:41 Jenna Phillips: Yeah, I'm young. I'm 28. I'll say, I know for, again, getting into enterprise and all of that, right? I'm young. But I've experienced a lot for where I am in terms of grief and loss and family, you know, stuff that a lot of that I think is what fuels me. I lost my mom at a young age and I have this kind of like need to like, I don't know how long I have here kind of, right? Like none of us know how long we have here. And so I want to constantly going to be getting better today and tomorrow for today and tomorrow. So, you know, when I am taking in content or when I am, you know, pushing myself on a deal, and I think like we do paper plate awards at Authenticx and I got the award of speed demon, which I think my boss sees as, as pros and cons because I am constantly trying to keep a deal as close, like the next meeting we're scheduling is going to be as close to today as possible, just because I like, I just don't know when, I just don't know what the future holds. And I want to get everything done when I can today. And I want to be the best that I can today. So I'm just motivated by being the best that I possibly can be and challenging myself and pushing myself to get better because, yeah, I honestly, you know, it may be a little unhealthy, but I feel like if I'm not getting better every day, that I'm going backwards and I start to panic. So that really motivates me. And I mean, I am motivated by being number one. I, you know, I don't talk to a lot of people about that because I don't love that I'm motivated by number one. And I don't know, it's not always celebrated, but I feel like this is a place that celebrates it so I can say that. I am motivated by being number one and, you know, I can motivate myself to sell all day long, but if I'm $5,000 short of somebody else, I am going to find a way to sell $5,000 more. Like it is just, I don't know, it's somewhere deep in my blood. If someone's $5,000 ahead of me, I have to figure out a way.

1:07:58 Scott Ingram: Love it. Love it. Well, let's keep going with this. And I know you kind of alluded to this before, but what is it that you believe That the average sales professional would think is crazy?

1:08:08 Jenna Phillips: Yeah, I think it goes kind of back to that. The 5, like if I'm $5,000 behind, like I'm going to get there. I'm gonna figure it out. I'm gonna find a way. But it's also that, you know, that the goal is a task. I don't sleep well until I feel confident that I'm going to reach my goal. And so like right now, because we're a startup, we're on a team goal and I've self-assessed that that is a little less motivating to me. Like when I have, this is your responsibility to the organization, you have to get this done. I can't sleep until I feel that I am going to be able to say I got that done. And I think it's something about like loyalty to the company. Like when I say I'm gonna be in something, like I want to be known as someone who's like, they're gonna be in, They're gonna get it done. They're gonna be there for like no matter what. And I just feel that need to get there. I think going back to the SDR side, I think, you know, I was, let's just be clear, I was only an SDR for like 8 months, but I do spend a lot of time with my SDRs and I think it also just teaches us a lot about sales in general. But I believe if you hire an SDR, which your goal is a little more You know, black and white. And if you have a goal that is, you know, 5 meetings a week, let's call it, I will not go home. I will not close my computer until I believe, you know, like if it's Monday and I haven't booked one and for 5 in a week, I need one on Monday. I'm working until, you know, late until I feel like I got one or I prepped myself to get 2 tomorrow morning. And that's not where I want to be. But if for some reason I need to be that way, then you better believe I'm getting up early on Tuesday and I'm figuring out a way to get to on Tuesday. So it's really that, that mentality of like, we don't get to stop until we get our goal. And I think that should go both ways, right? Like if I'm well above my goal, you know, for the week or the month that I've set for myself, okay, I'm going to You know, at 4 o'clock, my friend wants to go grab a drink or I need to go get a pedicure. I'm going to do that, that kind of thing. But when I'm not there, I'm not stopping until I get there.

1:10:36 Scott Ingram: Love it. Love it. What about the flip side? Is there something that the average or typical sales professional believes that you think is crazy?

1:10:43 Jenna Phillips: Yeah, I'm a big believer in it's always you, kind of like you can always control the situation. So. I think it's not necessarily something someone believes, but like early on in your career, or if you're just, you know, more trying to figure out how to get to the top kind of, right? People fall into the path of, oh, I lost this deal because this happened. Like that person or that other company, like they beat me and like there's no way I could have won because this happened. And I just think rarely is that the case. We did something that led to us losing and it happens. It's okay. Like you move on from it, right? Like it's going to happen all the time. Otherwise, you know, we'd be on here saying we have 100% close rate and nobody does, but we did something and there's something in the process that we can figure out that we did. And, you know, yeah, in the moment it might feel nice when you're talking to your boss to say, oh, well, we lost it because The, you know, security shut us out. Well, it's not gonna do any good for you in the long run, right? Like if you wanna get to that next level, owning the fact that maybe your lack of urgency or your lack of communication or your lack of asking the right questions around security made you lose the deal.

1:12:11 Scott Ingram: You know, it's, I'm coming back to, you talked about your speed. Paper Plate Award. Yeah. I think there's also an element of, I mean, we've, we've always kind of heard, you know, speed kills deals or time kills deals, not speed kills deals. You know, as you let things sit, I think it also just increases risk, right? Because stuff happens, right? There's, there's going to be a new variant. There's going to be an acquisition. Somebody's going to leave. And I think, you know, part of one of the things that I think you're controlling Is let me move this as quickly as I can, because that just minimizes the risk of some crazy outside factor taking things sideways.

1:12:53 Jenna Phillips: Yes. And at Canvas, when I first became an AE, Aman said to me, do you know why we hire salespeople? I think it was a moment where, you know, he, he asked me, if you're a local indie and you know Aman Brar, He can be intense. And he looked over, we were in a room, it was a room that, you know, 8 people could sit in, 2 little tables, that was it. And he leaned over and was like, hey, what's going on with this deal? And I said, oh, I haven't talked to him since Wednesday or something where I'm trying to get back on the calendar with them. And he was like, what do you mean? And I was like, again, I'm like months into being an AE. I'm like, I don't know. And he said, do you know why salespeople exist? And he said, the reason salespeople exist are to close deals faster than they would close naturally by themselves. Like, if you're not making the deal close quicker than it would if we just, you know, had them work with the website and look at the product and buy it on their own or with me, then there's no point. And so I think from then on, maybe, you know, I really try to move deals like days, I think, of a deal, you know, taking a meeting with a company on a Friday versus a Tuesday of a week because of scheduling. Well, that's 4 days added on to the lifecycle of the deal at minimum. But then, yeah, the risks of what happens in those 4 days, they lose the momentum. They, they, somebody else talks to them. There's so many things, right? And then we do that, especially now that we're in enterprise, right? Like if we do that, 8 times over, that's a month. And not only is it a month added to the sales cycle, it's a month added of risks.

1:14:38 Scott Ingram: Yeah. I mean, the other thing that you're doing that is a huge part of my process is, you know, just looking at your entire pipeline every day and thinking about every single deal and, okay, what can I do today to move this thing forward? Right. And that, that's game-changing. And I think a lot of people, to your point, like, oh, it's been a few days. I haven't done anything. Well, did you even think about it? Do you think about, you know, the excuse that you can make to reach out today to move something forward? Or is there somebody you can introduce them to or any of that stuff? Yes, exactly. So what advice do you have for somebody that is just starting out in their sales career today?

1:15:15 Jenna Phillips: Advice I have for someone just starting out is, first off, you control your career. So, you know, I think a lot of people Especially today, younger people enter the workforce or enter a sales job and they expect everyone to teach them what to do. So they expect like, well, that's my manager's job to teach me how to sell. Well, no, like your manager hired you to sell and yes, they're going to have training and enablement and whatnot. But, and probably this is how many startups I've been at or or the spaces I found myself in, but it's really your job to make yourself better at your job. Like, like it is your job to ask your manager for feedback, to ask your manager for advice, but it's your job to strengthen yourself, right? Like no one would ask, you know, no one would hire someone as a, as a fitness instructor and expect like, okay, I'm gonna hire you as a fitness instructor and then I'm gonna teach you everything you need to know to be a fitness instructor. No, they're going to expect you to come to, you know, have the certifications they probably need and like have worked out all of their life and know what they're going to teach. Right. They may give them, oh, here's some skill sets I want, or they may give them some advice, but it's on you to, to train yourself. And so find, you know, I like your phrase of, you know, your information diet or, you know, what you're taking in. Like, give yourself those appropriate places, like find those resources that are most helpful to you, but find your people too. I guess maybe know your learning style. And for me, my learning style is talking. It's engaging with people. So I know that about myself. So I probably read less books than a lot of people, but I put myself in a lot of situations where I'm talking about sales and I'm talking about businesses with people that I think are, you know, better at that than me so that I can learn from them and constantly, you know, strengthen my skill set. But then also, when you're just starting out, think about the company you're joining. Think about your end goal. What is your end result? Where do you want to be? Do you want to be a VP of sales? Do you want to be a CEO? Do you want to be a sales leader? And use that to decide where, or do you, or do you wanna be an enterprise account executive and crush it forever? And, and all of those places, like what goes into those roles and who do you need to be around? What places do you need to be around and what kind of product do you need to be selling, right? To like, that was another thing with me moving to Authenticx was realizing that HR tech sales, people are in that forever. A lot of times people sell HR tech and they sell HR tech for their entire career. And I wanted to broaden my skill set of what I've sold. So like just thinking about those kind of decisions as you choose where you go of what does that like, what story does that tell about you for the future? And Is it what you need right now? Great. And then is it what you need in 10 years? Is it what you need in 20 years? And if it's not, sometimes that's okay. But like, just know that and think about that. And then what, what do you need next? Like, if this is a good kind of toolkit or piece of the story for your story as a sales success, what other stories do you need to add and stories do you need to be able to tell? And like, how are you going to get those?

1:19:00 Scott Ingram: That is such good advice and it's relevant, not just if you're just starting your sales career. I think that's true throughout your career, right? And really considering where you're going and what you're doing. And you, you really spoke to, you know, surrounding yourself and learning through conversation. I'll call out 2 things. You know, we're now well over 1,000 tips into Daily Sales Tips, but the very first tip I ever gave, episode number 1, was kind of introducing the show. The second episode, I talked about how you have to own your own development, right? And I think that's really what you called out. It's so important because nobody else is going to do it for you. And it goes back to this 2% thing, right? Like maybe your organization cares about that 1 or 2%, but you need to care about it 100% because it's your career. It's your life. It's your profession. And accordingly, we had a little sidebar conversation and it is very, very likely that Jenna will be joining us at this year's Sales Sales Success Summit this October. And that's why I built this event, right? It's, it's so that we could be together and in a place where we can learn from the best of the best who are at the top of their game. And if you know about that event, you know that the only people that get to be on that stage are the folks who have been on this podcast. So by definition, they are number one, top 1% individual contributors. And this year's event is going to be We find a way every year to continue to raise the bar, and it's, it's going to be big. So Carly's going to be there, Jenna's going to be there. We want you to be there. So if you go to top1summit.com, you'll find the details on, on grabbing your ticket. And there's, there's also options on that to kind of set up a payment plan. You can actually just pay monthly, and it's, it's really not that big of a lift. So seriously consider if, if you are committed to being great and want to be number one or driven to be number one and to really perform well in sales, there is no better event. These aren't folks that, oh, I wrote a book, but I haven't actually sold anything in decades. Yeah, none of that. We're all doing it every day. So, Jenna, what advice would you have for somebody that is a little bit further into their career? And maybe they're at that place of like, I'm doing good. Like, I'm making my numbers, I'm doing okay. But they haven't found like that next gear. They haven't figured out to get to great and consistently be at number 1, what would you tell them?

1:21:29 Jenna Phillips: Yeah, Lucia did a training the other day that was around, you know, from 0 to there's a trophy of you outside, or there's a, there's a statue of you, you know, outside of your, your sports arena, your sports stadium. Like, where do you want to be? Like, where are you comfortable dying at? And thinking on that, like, like what, what is it for you? And it's okay. Some people, it's not, they don't want the statue, right? Like they don't wanna be that level, right? And that's totally cool. But it's knowing what it is for you. Like it's knowing what is important to you and like what is important that you result in and then building your plan from there. So I think regardless, if you're later in your career and you're thinking like, how I feel like I'm good, but I'm not the next level, it's analyzing like, where are the gaps? Like actually critically sitting down and, you know, kind of like you would a deal, analyzing yourself of like, where are the gaps to get me there? And what do I need? How do I fill that? Like, is it training that I need? Is it a habit that I need to build? Like, what part of the sales process do I struggle in the most? And thinking about that with a critical lens and then thinking about what you need to learn for that specific piece. And then where do you, how do you learn it? Is it, it could be going out to some kind of content pieces, could be going to someone that you know is really good at that. It could be just saying like, I just need to do this thing, right? Like maybe it's You know, I just need to stop doing X in my deals and start doing Y. And I'm just going to, before every call, remind myself that I'm… that's what I'm going to do, think about it, and then just do it.

1:23:25 Scott Ingram: You know, that's, that's a really interesting perspective. And I'm kind of personally reflecting on the front end of that and kind of starting with, well, you know, where do you really want to get? I mean, I'm actually been thinking about that a little bit in the context of I'm a huge Peloton guy. And my happy spot, you know, I feel like I'm performing well and I'm at the level that I want to be at if I'm in kind of the top 10%. Yep. I don't have a desire to be in the top 1% in the Peloton world because I probably don't have the right DNA to even do it. But the level of additional effort that I would have to put in to get there is more than I'm willing to commit. Like, nope, that's, that's good. I'm like really happy and satisfied in that 5 to 10% range. And sometimes like I really want to push and 5% would be great, but 1% ain't happening.

1:24:18 Jenna Phillips: Not going there. Yeah. And I mean, that's the example kind of I think of a lot of times. I mean, right. My, a lot of my family members are extreme athletes and I've seen the work that goes into that. And to me, at least right now where I am, like for me, I'm, Very similar. Like when it comes to, I have a Peloton as well, or working out. Like for me it's about health and about keeping myself healthy. And I wanna know that I showed up and I worked out and I'm keeping myself healthy. And like, that's where I am with that right now. That, that's where I am. I don't wanna be, I don't need to be great. I don't need to be really even like good at it. I wanna just know that I'm, I'm consistently doing it and showing up. And that's a big step for me from where I have been in the past. And so like, that's where I wanna be on that. And that's great. But like, I think a lot of people, That is in their mind where they kind of are, or that's what their behaviors are, at least in sales. And they don't stop to realize, like, do my behaviors and where I want to be, like, match up? Because, like, for me, it is that number one is I've… it's that or not in sales. And if I treated working out the same way that I treated sales, I'd probably be, you know, number one on the Peloton because that would be the effort I'd be putting in because I know I want to be there. But I I don't in that space. And so in each space of your life, understanding what's important to you.

1:25:36 Scott Ingram: Yeah. Love that. Are you comfortable sharing your Peloton username? I will.

1:25:41 Jenna Phillips: This will be good. This will be a good commitment for me. It is JPhillzz. So it's J-P-H-I-L-L-Z-Z-Z.

1:25:50 Scott Ingram: Ooh, very nice. Very nice. And you'll find me at SalesTechScott. And actually I ride under a Sales Success So, if you're a Peloton rider, follow, jump on, be fun to build some, some additional community around there. But again, I, going back to this idea, I think being intentional about, you know, where do you really want to be? What level of effort are you willing to put in? And then like, okay, now you know what you need to do and how far you need to go. Jenna, the last question I'll ask, well, maybe second to last, is when you think about the top sellers in other organizations, what do you wanna know about them? What do you wanna learn from them?

1:26:26 Jenna Phillips: From them? Yeah, I mean, a lot of things. I mean, I'm always wanting to learn, you know, what do you believe is… I love like your top 3 things. Like, what are the 3 things that you think like ride or die, these are them, without them I'm not as successful as I am? I always… I mean, because I think time management and organization is not my strong suit, I'm always liking to learn from other people. That are really good at that. But it kind of going back to our last question, like, I like to learn from people that are kind of like me and that's not their strong suit and how they keep themselves, you know, organized to what they need to be. Because, you know, I'm never… if you've met Eddie Schmeehl locally, one of my best friends, one of the most organized people ever. Like, his morning routine is like 8 steps. It's so thorough. And so I am never going to be him. I don't think ever that I would be that person. So, but like the people that are a little more like me on that side, like, okay, like how do you do it? How do you keep yourself organized and moving forward? But it's a lot of the enterprise too, right? I'm all ears for enterprise success right now. And you know, in that long, complex, multi-threaded deal, the secret sauce to a lot of that.

1:27:44 Scott Ingram: Awesome. Awesome. Awesome. So suggestion for you and anybody really, I always ask that top 3 questions at the front of every episode. So even if you don't want to listen to the whole thing and you want to listen to the first 10 minutes of each of these interview episodes, there are… I guess, I guess we're probably in the neighborhood of 400 of those top 3 things as we do the math on kind of all these, these episodes. So, Jenna, this has been a blast. We covered a lot of ground. I always try and wrap things up with something really actionable. So what would you challenge our listener to do over the course of the next week or 2 to improve themselves and improve their results?

1:28:22 Jenna Phillips: Yeah, I thought about this. I'm going to do 2, 2 challenges. One is on, and one is one I thought of before this, and one this conversation has made me have it. I said rose-colored glasses have been a challenge for me throughout my sales career. And so I challenge you to think about, you know, the question behind the question. There's a book that's called that too. That's really good. But okay, if you're going to ask a question that you typically ask at any stage in the sales process, what 3 other questions should you ask after that? Because it's bit me many times. I constantly try to improve upon that. And I'm going to do that this week with you all as well is Okay, as you're prepping for a conversation and here's the question you would normally ask, what are the 3 other questions that you should ask that make you go deeper so that you are not being caught by your own rose-colored glasses? And then the second one is around that kind of, as you know, we're starting the new year, I think when this will be airing. You know, look at yourself and at your pipeline. Look at with a very critical eye, you know, take an hour and sit down or 2 hours and sit down and say, okay, one, who do I want to be known as? You know, when I hang up my hat one day and, you know, finish my sales career, who do I want to be known as? That level that we talked about, what level do I want to be at and what gaps do I have in order to get there? And make a plan for the year of what do I need to fill in to get there? What gaps do I need to fill and what resources do I need to lean on? Resources meaning, you know, content people that I need to lean on to fill those gaps. And then also looking at my number for the year. And if, you know, if I, if it is that I want to be really great, that means maybe I want to be at 125% of goal for the year. What are the numbers that matter? To get you there? And how do you need to break that out, you know, each week, each month to make sure you're consistently working towards that so that you can think of that number as a task, not just a lofty goal.

1:30:41 Scott Ingram: Beautiful. Jenna, this has been amazing. Thank you for taking the time and sharing your story with us.

1:30:46 Jenna Phillips: Thank you. Thanks for having me. I appreciate it. Thanks for listening to the Sales Success Stories podcast. 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.