184: Morgan Cumiskey, Drata's Top AE on Overcoming Sales Challenges with Authenticity and Empathy

0:00 Scott Ingram: You're probably listening to this podcast to learn from the top 1%. However, there is no silver bullet. The top 1% get there by mastering all the fundamentals and intentionally working on specific areas of improvement to always sharpen the sword. The rest of this episode is brought to you completely uninterrupted thanks to The Sales Collective. Their secret sauce is helping you figure out the exact areas you need to improve compared to the top 1% using a mindset and skill-based assessment. They then offer training on those exact areas. They make figuring this out and developing where you need it easy. Head over to thesalescollective.com to learn more, or reach out to David Weiss on LinkedIn and let him know that Scott Ingram sent you. You're listening to the Sales Success Stories podcast, where we deconstruct world-class sales performers to provide insights and strategies to help 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 Morgan Cumiskey. Morgan is the top AE at Drata out of Nashville. Welcome to the show, Morgan.

1:20 Morgan Cumiskey: Hey, Scott. Super excited to be here.

1:22 Scott Ingram: Yeah, love to have you. Really excited that we're able to bring this together. And like we always do on the show, I love to start with immediate value. Let's talk about the top 3 things that you believe have contributed the most to your success in sales?

1:37 Morgan Cumiskey: Yeah, definitely. It's certainly hard to boil it down to just 3 things, but if I had to put a number on the top 3, I'd say starting with working in the partnerships channel. Obviously every sales organization is probably going to look a little bit different, but here at Drata, we have the ability and the luxury of working with service partners, resellers, MSSPs, essentially any type of organization that helps our customers outside of what our services can actually provide. And so by building those relationships with our service partners, our resellers, MSSPs, it allows me to have a really healthy pipeline all the time because they have great relationships with their customers, with our customers. It makes the relationship with the customer even better because you have somebody who's selling on your behalf when you're not there and they can bring you warm leads. So who wouldn't want a stronger pipeline with better relationships? So I would say that's probably the number one thing that I do to keep my pipeline healthy. The second thing is really having strong internal relationships. So as we go into our conversation today, you'll probably see a theme of just building relationships and the reasons why I've been successful as a seller at Drata. I really wholeheartedly believe in never losing a deal alone. And what that really means for me is making sure that I have strong relationships cross-functionally with customer success, with product, with the executive and maybe leaders at my team, even with my SDR. Obviously, every sales organization looks different. Here at Drata, some of the sales cycles can get really complex, and I want to make sure that all of the relationships that I have internally are strong. So if I do need to go and ask for a different part of the business for assistance on something, they're more than willing to help me out. And also, it helps me speak in my sales cycles to how our customer success org will, will help them, because I know them personally and I know how they work, and I can speak from personal experience. And the third thing is, and I think this is probably the most important, and not talked about enough in the sales world is just your mindset and having an abundance mindset. I try so hard to show up to every single conversation that I have like I'm already at 100%. I think buyers, especially nowadays, they don't wanna be sold to, and they can smell that when you come to a conversation and you're eager to close a deal and you're working on your timeline, and they're very turned off by that these days. So going into every single conversation with an abundance mindset, even if you're down for the month, if you're down for the quarter, making sure that you're still radiating positive energy and knowing that as long as you put in the work, yes, sales is a numbers game. It's going to come back to you. So just making sure that you keep your mind right, you're doing things outside of work to come in and show up your best every single day has really helped me to be consistent as a seller.

4:12 Scott Ingram: These are so good. Let's maybe talk about them in reverse order because I think we can all probably agree that we are a different seller. We are a better seller and probably a better human when we're ahead of our numbers and we're maybe not doing the right things as much when we're behind our numbers. How do you get yourself in that mindset when you're not there, right? Or, oh my gosh, start of a new quarter, there's a zero on the leaderboard. How do you put yourself in that frame of mind where I'm gonna act as if I am ahead of the way so that I'm doing all the right behaviors all the time?

4:49 Morgan Cumiskey: Yeah, I mean, for me personally, I think it sounds so woo-woo, but I really try to start my day without looking at my phone. I think when you're in sales, it's very hard to not wake up, open your computer, check your email, check your cell phone. It all starts with the way that I wake up every single day. I try to wake up every single day. I put myself in a positive mindset. I listen to a 10-minute guided meditation to really get my blood pressure down, especially if it's December 1st, it's the last week of the quarter or the first of a new quarter and I'm at zero. That can cause some anxiety, right? So I try to wake up every single day. I do 10 minutes of meditation. I try to get outside and get some sunlight. I disconnect from work for just a little bit before I actually open my laptop and start what I'm doing. And then I just go back to the basics. I've been selling for almost 5 years and the basics are always there for me. So I know that if my pipeline is light, if I'm staring at a big zero, what do I need to do? I probably need to do some prospecting. And if I've done those things throughout the quarters, I probably won't be sitting at, you know, a light pipeline or really be staring at a zero that's daunting to me. So just making sure that I'm showing up and doing those little things every single day. I'm really leaning on my teammates too. So I work in a completely remote environment and it can be difficult sometimes not to feel super isolated. So hopping on a quick 10-minute Zoom call with one of my teammates, talking about what's working for them, just getting into a really positive mindset, being able to radiate that with the conversations that I'm having.

6:13 Scott Ingram: Love that. Love that. And perfect transition to the way that you're managing those internal relationships, especially being 100% remote. So let's talk about 2 sides of this. I'm interested in understanding just how are you maintaining those relationships? Relationships, and then how are you leveraging them throughout your deal cycle?

6:33 Morgan Cumiskey: Yeah, it's a great question. I think the maintaining side is obviously more difficult when you're in a fully remote environment. I used to work at companies where we were in the office every single day. It's so much easier to go over to someone's desk, talk to them, have lunch with them, really nurture those relationships because you can just get up out of your seat, go walk over and say hi, introduce yourself. It's a lot more difficult in a remote environment. So it does take a little bit more effort to make the relationships and then also maintain them. I've found that in a remote environment, it's so much easier to maintain the relationships if you can show up to them and add value. I make sure that it's a 2-way street. I'm not going to my customer success team and asking them to join calls for me to help sell with me if I'm not also bringing them value too. So every single time that I'm closing a deal, I'm making sure that all of my notes are really nice in Salesforce, that the customer success team is going to have a really easy, smooth transition because of the work that I put in upfront. And that makes them respect me across the org. So when I do need to go nurture those relationships or ask them for any type of assistance that will impact my deal, they know that I put the work in, put my best foot forward to make their lives easier too. I think as sellers, sometimes we can get into this mindset of like, ask, ask, ask. And we want to make sure that we're adding that additional value to other parts of the organizations too. So, and then to answer the second part of your question, anytime that I'm in a deal and maybe some areas have come up that I can't necessarily speak to personally, I always try to tell stories to my customers of success that we've had in their industry or success that we've had of customers like them. So when I'm looking at the whole sales cycle, maybe going back to kind of customer success or even product, if there's not something that I can speak to from a personal experience or tell a story about, I'll make sure to tap somebody else in my organization who can come on the call, show the face and say, hey, you might even be working with me personally. And they can tell a story to the customer, a success story from like a real life experience versus having, you know, a salesperson do that. Yeah.

8:36 Scott Ingram: Yeah. So good. And I think the more that you can kind of connect those dots between, hey, here's somebody else in my organization who doesn't carry a quota, who can tell you this story of kind of this shared experience and doesn't have quite as much direct skin in the game and it maybe has a little bit more credibility because of that, because it's just a different incentive structure.

8:54 Morgan Cumiskey: Yeah, exactly. Obviously people buy from people they trust. It kind of goes back to me working on my timeline, doing what's best for the customer. So bringing in somebody, like you said, who doesn't carry a quota, obviously buyers can kind of smell that sometimes. And just putting another face to the name helps kind of ease any skepticism that they might be having about what I'm showing them, what I'm saying. It's like, hey, Talk to somebody who's doing this every single day, who works with customers like you every single day, who might actually be supporting you when you become a customer. It just helps ease some of that skepticism.

9:22 Scott Ingram: Yeah. And then finally, let's talk about the partnerships channel, because it sounds like my understanding is this is sort of a thing that's available to everybody on your team, but you've just found maybe particular success and have leaned into it. What was that? Did you understand that right away or did you just kind of find, oh wow, this is working way better than maybe my more traditional kind of cold outreach types of, types of efforts?

9:43 Morgan Cumiskey: Yeah, so I'm like every salesperson and prospecting is not something that I wake up every single day excited to do. I don't like to make cold calls. I don't want to make 100 a day. We actually had a sales kickoff about a year ago today where one of our head of partnerships got up on stage and he said partnerships is going to be the way that the most successful reps here at this company are going to flourish, hit their quotas, exceed their quotas. And I really listened to that. I took it to heart and throughout the sales cycles that I've been in at Drata, I've noticed that a lot of them come from strong relationships. Mine in particular is in the cybersecurity space. So as you can imagine, the people that we sell to are skeptical by nature. They're typically CISOs, they're security folks, they're engineering folks. They really speak in a different language. I knew that by nurturing the channel with people and companies who had existing relationships and trust with our customer base was going to really help me flourish as a seller. What I did was for about 6 months, so half a year, I made sure that I was reaching out to almost every single MSSP reseller channel partner that we had and started building and nurturing those relationships. Again, it's a 2-way street. So I wasn't just asking them like, hey, do you have customers who are going to be a good fit for Drata? They also have services that they offer to our customers. So a lot of the resellers that we work with have offered things like pen tests or different types of services. So It goes back to not losing a deal alone. Every single deal that I have at Drata, I'm trying to plug in one of our service providers to do a service that we don't do today, whether that's like a pen test or an audit or whatever the case is. So I'm passing them deals, they're passing me back deals. It's a two-way street, but I really made sure that I was filling their pipelines just as much as they were filling mine and making sure that I was going to be their point of contact if a deal ended up coming through that did need for our services. So I think one of the first things is like, nurture their relationships, get to know them as a person, ask about their kids, ask what their favorite coffee drink is, send them a Starbucks, get to know them on a personal level, and then add value to their pipeline too. Most of the service partners we work with, they also carry quotas. So I want to always make sure that it's a two-way street and I'm doing what I can to pass them deals back.

11:51 Scott Ingram: Nice. Nice. Have you found… I mean, having kind of run this play over the last number of months, have you found certain partners or certain individuals, like you're just kind of clicking and you're getting more deal volume from them, or are you finding it pretty consistently sort of across the folks that you're reaching out to?

12:07 Morgan Cumiskey: Yeah, I think there's definitely a few that I have in particular that the volume is higher. And to be honest, it's the ones that I have better relationships with. I've became good friends with some of these service partners to the point where I've flown out of state to go see them. They've came to my home base here in Nashville to see me. It is usually the ones that you build better relationships with and you get to know them on a personal basis and then They want to work with you. They also get to know how you work as a seller and you get to learn how they work as a seller. So then they prefer to work with you other than working with multiple different reps across multiple different deals. They know that you're going to come in, get the job done. You show up, you do what you say you're going to do. You make it easy for them. You've removed the friction in the sales cycle, and then they want to work with you more. It's mostly building the relationship and then showing up and doing what you say you're going to do. That way they know that they can trust you with their customer who they probably have a larger service offering. Deal with that we may have a small piece of the pie. So they want to know that when they introduce me to a deal, I'm going to come in and show up as my best self and add value immediately to their customer and then follow through on the things that I say I'm going to do. Yeah.

13:11 Scott Ingram: Yeah. At the end of the day, it really is that transference of trust. Like if you do a good job, they have trust with their client and you get to kind of borrow that and ride on top of it. But it's super important that you de-risk that for them and maintain that trust because you don't want to blow up their deal. You're like, I trusted you. And then what did you just bring me? What was that? 100%. That's dangerous.

13:30 Morgan Cumiskey: Sometimes it's like your partner hands you the keys to their Porsche and they say, take it for a test drive. And they want to know that you're not going to hit a couple curves, knock over a couple mailboxes. They want to make sure that that car is coming back into the driveway exactly like they left it, or you're going to go get it detailed for them and it's going to come back even better. Always leading with that mindset.

13:48 Scott Ingram: Nice. Nice. Don't Ferris Bueller valet the car.

13:51 Morgan Cumiskey: Yeah. And I hope none of my partners ever let me drive their Porsche because that would be a bad decision on their side.

13:58 Scott Ingram: I love it. Let's contextualize. Talk about what exactly is your role and how did you get to number 1 at Drata?

14:04 Morgan Cumiskey: Yeah, so I am a commercial account executive. It's changed quite a bit over the course of the 3 and a half years that we've been a company. I would very much still consider us a startup. In my role, I work with companies up to a specific size. So we look at commercial as employee size. What's really helped me get to number 1 is just I guess number one is the relationships, but also just going in with a relentless mindset and making sure that I'm showing up as my best self every day. I'm doing the things that I know that I need to do to be consistent and be successful. When I started at Drata, it very much wasn't like that. During my first 3 months as an AE here, I almost quit sales. I almost gave up on the organization completely. I just couldn't get it right. And then I quickly realized that I just wasn't focused on the right things. I think one of the things that is really important as a seller, if you want to, number one, earn the trust of your customers, is to get to know the industry and not just your product. And I think that's where I fell short for quite a bit of time until I finally caught my groove, especially in the cybersecurity space. The people that you sell to are really passionate about what they do. I took the time, I spent a lot of time on YouTube. I really got to know my industry and what my buyers really cared about. And that's allowed me to show up to every single conversation, not as a seller, but more as a trusted advisor. So I want to make sure that every time I'm coming to a conversation, I'm bringing value. I can even share insights from what I'm seeing in the field. I can speak their language and really level with some of the pain points that they're experiencing versus just coming in and showcasing what our product does when I may not even know if it really means anything to them. So I think what's really helped me over the past couple of years being here is really getting to know the industry, the people we sell to, the pain points they care about, and then making sure that I'm asking questions around that and then also adding value, bringing educational content to what I'm doing, not sending them content about Drata, but sending them content about the cybersecurity industry, what we're seeing, insights that our experts are finding in the field. Again, it really goes back to being able to have them see you as an advisor, a consultant, and not like this salesperson who's just pushing product at them all the time.

16:12 Scott Ingram: Yeah, so important. I mean, almost every organization has all kinds of help that they will give you to get product knowledge. What I rarely see, which you just said is way more important, is getting buyer knowledge. How do you really understand just the ins and outs of your buyer and what they're dealing with and just being able, because if you can't get inside their head, you can't connect the dots with all the product knowledge. All the product knowledge in the world is going to be useless if you don't understand how does this actually work in context?

16:43 Morgan Cumiskey: Yeah. And that's exactly right. It's like, you know, as a seller, you can find out who are the top 3 typically people that you're selling to, who cares about the problem that you're solving. And then from there, you can kind of workshop that backwards to say, okay, great, here are the 3 people that I'm typically going to be selling to. What do they care about? And you don't even need to go on YouTube to find out. You have a customer base that you can go and talk to, and you have customers who you've probably sold to in the past. Talk to them, set up meetings with them, ask them for 10 minutes of their time and say, hey, when you bought X, Y, and Z product, why did you buy it? What pain points did this solve for you? And you can build out an entire list of a battle card or even like a discovery workflow based on those challenges that real customers that you've sold to, or maybe your company has sold to, has seen. You don't even need to do a ton of research. Just go talk to the customers that you guys have sold to, right? Or ask your business to set up a meeting with a customer and say, hey, we want to ask them a few questions about why they bought our product. What are we making better for them? What can we improve upon? And then you can take all that feedback and start to weave it into just having a really strong understanding of what's important. And then you can take all of that to your conversations. And as you said, showing up and building that trust.

17:57 Scott Ingram: Yeah. And same thing. I think you can even extend that into just your understanding of the competitive landscape. So to your point, I mean, I'm talking to somebody that bought our solution. What else did you consider at the time? Like, why didn't you buy that? And just really getting from the buyer's voice, like, this is what they're saying. It's in their own words. And if you work on those relationships, Now you've got customers that you can connect with your prospects as well. Like, hey, don't take my word for it. Here's somebody that went through the same journey that you're embarking upon. They're just 6 months ahead of you or whatever.

18:27 Morgan Cumiskey: Yeah, absolutely. And don't even stop there. Like, ask the people who didn't buy your software why they didn't buy it. There's no better opportunity than when you lose a deal to ask them why you lost it. And sometimes they won't answer you or they won't get back to you. But if you've spent a good bit of time nurturing the relationship, building the trust, they'll tell you. And if you're a thought leader at your company, number one, you can take that feedback to whatever department needs to hear it, whether that's product, CS, engineering. Maybe it was a feature gap. Maybe it was an integration gap. Whatever the case is, you can take that feedback internally to make your product better. Maybe it was something that you missed as a seller. Like I've had and lost plenty of deals for things that we couldn't solve for. And I just didn't ask the question, find out why you lost the deal. And maybe it is something related to your overall offering, right? Or something that was just missed in the sale. But I think that's a perfect opportunity. Like ask the people who didn't buy your software, what did we miss? Why didn't you move forward with us? What could we have done better? What did you like? I think every interaction that you have, whether it's a customer, a closed lost deal, a current prospect, is always an area for you to be asking for feedback. And that just helps you show up better to the next one.

19:29 Scott Ingram: Absolutely. And then going back to the internal relationships, those are things of value that you can bring back to the organization like, oh, we didn't have this feature, so the product team needs to know about that, or we're not showcasing this enough. So let me take that to product marketing or whoever it is. Morgan, before I really start to unpack all of this and figure out all of the different ways that you are sort of tackling your territory and everything else, quantify your results for us. What have you done to become number one?

19:56 Morgan Cumiskey: Yeah, I think number one, it goes back to really having a relentless ownership of your business, making sure that quarter over quarter you have deals, you know where the deals are at. You know the next step in every single opportunity and you really treat it like your own business. So one of the things that I got really good at in terms of quantifying where I needed to be in order to be successful is having a really clear understanding of how many deals I needed to get to a specific number. What is my close percentage rate against those deals? What is my average sales price? How many new opportunities do I need to have every single quarter? In order to potentially backfill for some of the ones that are not going to close. I have a very lengthy Excel sheet. It's probably not the most automated way to keep track of it, but every single quarter I'm filling out that Excel sheet. Obviously we use Salesforce, which is a great tool too, but I like to have a little bit more visuals. I color code it. So I always like to go through and every single quarter I fill out the deals that I currently have. I'll mark them red, green, and yellow just based on whether I think they're at risk. Maybe if we don't have clear next steps in place, those would be considered red. Maybe yellow ones are ones that, yes, the deal's moving forward, but we don't necessarily have a compelling event for them to close this quarter. And then greens are ones that I feel really confident in closing. Potentially those would be in commit. So every single quarter I do kind of like a pipeline scrub, try to get a really clear idea of where my business is at. And then from there, I work very closely with my SDR to make sure that we're aligned on, okay, great. If these deals don't come through, what else are we bringing to the table? It's something that I'm very passionate about, and I'm sure we'll talk more about it, is working with SDRs. I used to be an SDR for 3 years. It's one of the ways that I fell in love with sales. So I have a very close relationship with my SDR. We're constantly trying to figure out new ways to break into new accounts. I'm constantly trying to build her up and make sure that she's still motivated. Every single quarter we're doing kind of like an inventory of what do we have? What do we need? How are we going to be successful and kind of go from there.

21:57 Scott Ingram: When you look at, it sounds like you're kind of working backwards. Where are you setting your target? So when you start a quarter, when you start a year, where are you setting kind of that end goal for yourself? Yeah.

22:08 Morgan Cumiskey: So when it comes to like pipeline, I always try to have around a 2.5 to 3x pipeline coverage. That's always what I'm aiming for. So if my quota is, let's call it $300K per quarter, I want to make sure that I have 2.5x more pipeline than what my current goal is. So that's kind of always what I'm shooting for and active deals within my current pipeline. With that, it always allows me to know that if my win rate is X and I have X amount of pipeline coverage against my current quota, I'll hit or exceed my number. I'm always shooting for overachievement. I know that's not everybody's forte. I always try to get to around 100. If I don't get to 120%, I'm like, dang, that wasn't a good quarter. But I'm always trying to make sure that I have 2.5x, 3x pipeline coverage to make sure that those deals are going to close. And then if I have backfills for the ones that don't.

22:54 Scott Ingram: Love it. Love it. Let's go back to the beginning. What's your origin story? How did you get into sales in the first place?

23:01 Morgan Cumiskey: Yeah, I feel like it's pretty similar to every salesperson ever. I went to college for something that I didn't use my degree in. So I spent 4 years at Coastal Carolina University out of Myrtle Beach. I actually studied kinesiology, so I really wanted to be an occupational therapist. I grew up in a household and a family of bodybuilders. My parents were bodybuilders growing up, and so I had a very strong passion for the gym and working out, which I still carry today. But in that, I really developed a love for helping people, and that's where I think I started to lean towards the occupational therapy, physical therapy route. 'Cause I knew that I could wake up every single day, solve problems, help people. I could really put my heart and soul into what I was doing. I knew that the people on the receiving end of what I was bringing to the table were actually gonna be benefiting in their real life from working with me. I very quickly realized that I was so bad at chemistry and it just wasn't gonna happen. I graduated college and I got my first job at this company called Forrester Market Research. And in that experience, I started working with a lot of these really big B2C and B2B brands. And I got to shadow some really, really talented, successful account managers at the time. And I really fell in love with how they would consult with these businesses and bring solutions to the table, solve their problems on a really massive scale. I mean, they were working with Fortune 500 companies. And from there, I really knew that sales is where I wanted to be, but it wasn't on the account management side. I really found myself being more of like a hunter, wanting to kind of go out and create new opportunities. But I think it always kind of stemmed from my desire to help people solve problems. Now I know software is not curing cancer, but you do to a degree, if you care about what you do, get to go out and solve real problems for your customers. And I think that's what makes me and keeps me motivated is a lot of the customers that I work with today, this is their business. These are sometimes startups, sometimes they're large companies, but at the end of the day, what we do at Drata really is a staple in making their business successful. And if you truly take the time to understand, how am I going to help this person? What do they care about? What am I doing to make their life easier? It really helps me get up in the morning and sleep at night on my pillow, just knowing that I'm helping solve problems. So I think that's where it stems from, is just kind of the desire to help people.

25:19 Scott Ingram: Love that. And then you spent a good chunk of time as an SDR. Talk about that experience. And then I'd love to hear your perspective on how to really have a great SDR-AE relationship since you've been really thoughtful about being on both sides of that relationship.

25:35 Morgan Cumiskey: Yeah, being an SDR is such a grind and anyone who's been an SDR just would probably agree with that. But man, it is so much fun. You learn so much as an SDR. I've been an SDR at, I think, 3 different organizations at this point. I've learned a lot in that. I've been rejected a lot in that. It really helps you develop thick skin as a seller. I think one of the biggest things that we have to overcome is just like rejection. You're not going to win every single deal. And being an SDR really teaches you to have thick skin because you're going to get hung up on. You're going to have people tell you to kick rocks all the time. And it really helps you develop a really clear, defined idea and methodology as far as what is discovery. I see a lot of really, really, really successful sellers are typically the ones who are SDRs first. And it's because you have to know how to ask questions, the right questions to ask, when to ask them to really peel back and uncover that pain. When you're an SDR, that's kind of part of your job is like you're cold calling people and yes, you're trying to book meetings, but you're also trying to uncover pain. You're trying to figure out, do they need what we're selling? And do they have a desire to book a call with us? As an SDR, I really learned how to do really good discovery and peel back layers of pain and really get buy-in for people to want to meet with us. And I've taken that into now my time as an AE, being able to level with my SDR in some ways and be able to provide her with insights into what worked for me when I was an SDR, but also help kind of nurture her as an SDR because most SDRs that you work with nowadays, they want to be AEs in the future. So one of the things that I try to make sure that I do is not only, hey, we're going to work together on some of these accounts, but what do you need from me? How can I help you be better in your role every single day? What are the next steps for you? Do you want to be an AE or do you want to do something different? And how can I help you get there? I really try to nurture that relationship with her and just like, hey, yes, I'm your AE, but I want us to feel like we're equals in this. And if she asks me for something, I go and do it. So I'm not just sending her accounts saying, hey, break into these. She actually is such a rockstar. I have to give props to her. She's one of the best SDRs I've ever worked with, but she gives me homework. We have weekly meetings where she'll write homework for me of accounts that she wants me to break into, the people that she wants me to go and connect with on LinkedIn or make a dial to or send an email to. So she makes it really frictionless for me to help her and her outreach, but we just have such a good working relationship that it's been so amazing to work with her. But if your SDRs aren't giving you homework, ask them to. We're so busy every single day that sometimes things just get totally lost in the shuffle. And she keeps me accountable. She'll hit me up on Slack and say, hey, Hey, you didn't do what you say you were going to do. And I'm like, you're right. And I'll do it right then. So she really, really helps me stay accountable because obviously my day can get just so busy. But I always try to make sure that I'm blocking my day. I'm making sure I have an hour of prospecting every single day. She's tagged on that on my calendar. So she knows if I'm not doing it, we always just try to keep that level of accountability with each other.

28:30 Scott Ingram: Yeah. So good. So good. Knowing all that, you know, now and having been through this adventure, if you were starting over in this moment, what, if anything, would you do different? How would you sort of tackle the start of your sales career?

28:42 Morgan Cumiskey: That's a really good question. I think when I started as a seller, it was like drinking from a fire hose. There was so much information out there. I felt like there was so many things that I had to learn. I had to learn how to do better discovery. I had to learn how to manage deals. I had to learn how to negotiate, close. Like there were so many things that I felt like were gaps in my current knowledge. And what I didn't do was find one or two people's style that I really liked. And I was looking at, we use Gong here and most companies that I've worked with have used Gong. What I was doing was I was just watching Gong calls of recordings from discoveries, from negotiations, from demos, from all these different areas, from product that I felt like I had to learn. And I was watching them from 30 different reps. And so everyone has their different style of like how they like to sell, how they like to negotiate. And it made it really difficult for me to kind of find my groove because I was just hearing all these different talk tracks across the board. So what I wish I would have done, and this is what I typically will tell any younger seller that I'm helping or SDRs who want to become AEs, is find one or 2 people that you really resonate with the way that they sell, the way that they speak, even the way that they show up to calls and watch their calls religiously. Make a script if you have to, and really try to get good at mimicking what they do. And then put your own personal pizzazz on it when you feel like you're ready. But there's so many different things that we have to learn and it can get really confusing. So I would tell myself like, hey, find 1 or 2 people that you really like the way they sell and try to mimic what they do to get comfortable. And then go in and add your own personal style on it. Cause that certainly would have helped me in the beginning.

30:22 Scott Ingram: That is such good advice. And I think it's good advice you can apply to this show. This is a firehose of greatness. You're hearing insights from all kinds of different incredible sellers, but if you find those that Their approach, like their style seems best aligned with me and just going deeper. That's the episode you listen to once a month and really go back to, or you reach out to them and say, hey Morgan, this connected with me. And you build that relationship is, I think, so powerful. What an incredible idea. You've given me something to think about in that. So the show's called Sales Success Stories. What's your favorite success story? What's your favorite story of a sale? Maybe it was your favorite failure story. Sometimes those are the ones that stick the most because we learn so much from them.

31:09 Morgan Cumiskey: Yeah. I mean, that's a tough question because I have so many, I feel like really happy, blissful moments of just deals that I've worked really hard to get. And honestly, I think the one that comes to mind is not even a deal that closed. It's actually a deal that is still open. I would even almost consider it a closed loss deal at this point, but it's a company that had spoke with us in the past about a year ago. Me and my SDR identified it and said, hey, the things that they didn't have with our product, we have them now. So let's give this another shot. My SDR and I worked really hard. We reached out, we prospected for a few months. We finally got the meeting. And when we got the meeting, we ran a very, very in-depth discovery call over the course of maybe 5 to 6 months, which is a fairly long sales cycle for the segment that I'm in. We ran a very, very extensive proof of concept, and in that time, I got to know our point of contact very personally. She has a very impressive pedigree in cybersecurity. She actually was in the Air Force for cybersecurity for about 10 years. So I grew to really respect her as a person and the way that she manages her team and her business. We got to know her very, very well, and in that, I think the reason why this is one of my happiest, most blissful sales stories is I really fired on every single cylinder and goes back to the top 3 things that I mentioned at the beginning of this podcast and the way that I showed up in that deal. I brought in product, I brought in customer success. There was things within that sales cycle that I just wasn't going to speak to as well as my counterparts cross-functionally were. We had to jump over hoops to actually get product timelines moved up. And again, that's not something that would have ever been possible if I didn't have those relationships internally. So I was able to go and make those asks. We worked in the partner channel, so we were working on getting this deal pushed through a reseller that she had already had a relationship with that was selling on her behalf when even we weren't there. And the abundance mindset… I had to show up every single day knowing that we had gaps within our current offering for this customer and still showing up every single day and trying to make it work, trying to find out where we could potentially fill the gaps or make up for some of the things that we just didn't have at the time. Unfortunately, this deal did not close. One, it was actually a deal that I had forecasted for this quarter, but because of the relationship and the value that we brought to this particular company and to this prospect, she has agreed to continue to talk with us and potentially engage in an agreement in January of this year. They've extended their current contract with their current provider out just a few months. So we even got her to say, hey, I'm not going to sign. A 1-year agreement with this provider that we're currently with. We're going to go month to month with them to give you guys the opportunity to come back to the table. And that never would have been possible if we didn't show up every single day with the mindset of like, hey, we're going to make this work. We may not be winning this deal and this call right now, but we could win it in the future using those internal relationships, bringing in product, bringing in customer success, and then bringing in somebody who's going to sell on our behalf. So I think the reason why I'm so proud of this deal is I did everything that I possibly could. And even though it didn't result in a win, it might result in a win in the future. And I built such a good relationship with her that even if we don't sell to her company, she's already agreed to be more than happy to be a referral for me. I think I'm just really proud of the relationship that I built with her and the relationships that I built internally that allowed me to make some of those asks happen and really happy about that. So yeah, not like a super happy, like, hey, closed one story, but But one that I'm still super excited about. I mean, it would be a really cool logo to bring home one day. So hopefully the next time that we talk, Scott, I will be updating you that we got the deal and can celebrate that.

34:50 Scott Ingram: Absolutely. And I love this idea of being proud of the way you sell. Sometimes you have to just disconnect from the outcome because there's things that are not in your control. Like, I can't control what our product ultimately does and doesn't do. Maybe it's just not the right fit, but I did everything I could. That's fantastic. You've had a lot of success. You have been a consistent top performer in this and other roles. What are you most proud of?

35:12 Morgan Cumiskey: That's a really good question. What am I most proud of? I think I'm just proud of how I show up every day. I think it's really easy to, number one, get down in the dumps when you're not having a good quarter or you're not exceeding your targets, especially when you are performing at the top of your leaderboard. It's hard not to get in your head when you have a down month and you're like, hey, I've set this expectation. People are counting on me to bring in this amount of revenue. You do feel a lot of pressure in that. It's very easy to get down in the dumps. And then on the flip side of that, it's really easy to get super overconfident and cocky in your work. I think I'm really proud of just the mentality and mindset that I've been able to bring to my company's culture. And as much as I have been with the company for over 2 years and we're only 3 and a half years old as a business, I would say that some people would say I'm like an OG at the company. I always make sure that I'm reaching out to all the new people. I always want to make sure that I'm showing up with a smiling face and that I'm being friendly and open and honest and leading with integrity, trying to do the right thing and just showing up with a good attitude. Not everything's going to be perfect all the time, and that's okay. I always just try to show up with a really good attitude and a good mindset and make sure that the person who's receiving my energy is receiving something positive and that I'm trying to bring just good vibes all the time, even when things are hard and solutions too. Like if a problem comes up, I always try to make sure I'm bringing solutions to that. So I'm really proud of just the brand that I've built for myself and the mentality that I try to show up with every day. Obviously it's not perfect all the time. I think that's probably what I'm most proud of.

36:43 Scott Ingram: Nice. What about the other side of that coin? What's the biggest challenge? What do you struggle with the most?

36:49 Morgan Cumiskey: I struggle with a perfectionist mindset all the time. It's hard when you have a down month, a down week, a down quarter to not look at that and really have to do some internal reflecting on, okay, what did I do wrong? What am I doing right? So I think sometimes it's just getting out of that perfectionist mindset of there's going to be ebbs and flows, just like everything in life. There's seasons and waves of just change and being able to be open to knowing like, hey, I can't be perfect. I'm going to miss some steps sometimes and not being as hard on myself when I'm doing that has probably been the most challenging thing being a seller and especially being in a company that's so fast growing and fast paced and aggressive in the targets that we set out for ourselves. And then once you get to that point where you are finding your stride and you are becoming a top performer, it's like, hey, you want to make sure that you're maintaining that top spot. It's definitely difficult to not get in your head when things are not going super well, but just making sure to like stay grounded and do the things that you know that you can do has helped. But yeah, that's probably the thing that's been the most challenging.

37:50 Scott Ingram: Say a little bit more about that, just in terms of how do you work through it? How do you work through the, I have really high expectations for myself and things aren't always going to go the way that I want them to go. So when you're in those dips, How are you just making sure that you come out cleanly and don't get stuck there?

38:07 Morgan Cumiskey: Yeah, I mean, it's really simple for me. Like sometimes I, especially like working in a remote environment, I can catch myself being behind my computer screen for multiple hours at a time. We're human beings and we need sunlight. We need fresh air. Sometimes it's as simple as just like going for a walk. If I'm like, hey, I'm struggling with this and I can't wrap my mind around what I need to do next, I step outside and I get some fresh air. Sometimes it's really as simple as that. I need to disconnect from work for a moment and just get back to my mindset and my mentality, realizing that I'm a person. I can go outside, walk my dog. Sometimes it's as simple as that. Sometimes I really lean on my teammates and my, my leadership to get me out of my ruts. I'm very fortunate enough to have a leader here on my team who I made a LinkedIn post about this actually very recently where I messaged him at the end of last quarter and I said, hey, I'm in a slump and I'm really over this. Like I was getting really frustrated. I hadn't closed a deal in a really long time. I was starting to not see the light at the end of the tunnel for getting to my number. This was me coming off of a 9-month consecutive quarter of month over month hitting my number. And I was putting a lot of pressure on myself to get to that next month and consistently hit that target. But I sent him a message and I said, hey, I'm in a slump and I don't like this. And he immediately popped me on a Zoom call. What you would expect from a manager in that moment is a pipeline review. Where are your deals at? What can we bring in? What can we pull forward? What can we do better? And instead, he asked me a few simple questions about how I can fix my mentality. He said, if you woke up every single day and you had an abundant life, what would it look like? And he made me write it down. And then he said, today, what are you grateful for? And he made me write it down. And then he said, today you can surrender. And then he made me write it down. And it really got me in a positive way of thinking. And again, I'm very fortunate to have a manager who shows up to conversations in this way. I know not everybody is. And it just got me out of my head. And instead of him scrutinizing my pipeline, he got on the call and said like, hey, how can we fix the way that you're thinking about this? You have deals. There is abundance of companies you can call on, CloseLoft you can go to. ACV that you can add to your current opportunities. Like you need to get out of the scarcity mindset. There's so many ways that you can add more, more, more, and you just have to think about it like that. So then that same day he got on an hour-long call with me and we actually did a cold call block and we booked 2 meetings. So sometimes it really is just like getting out of your own way, but leaning on people that, you know, can kind of bring that to you internally. And for me, that's my manager. Sometimes it's other colleagues that I work with who I see are performing really well and maybe they're quarters that I'm not. And I just go to them and I say, hey, what are you doing that's working? Lean on the people that you work with. Sales is obviously not a team sport, but it is. And you have teammates that you can lean on. So if you see people who are performing and maybe you're in a, in a rut, just ask them like, hey, what's working? And if you've built those relationships and that trust with them, I'm sure they would be more than happy to help you in the ways that you've probably helped them in the past.

41:06 Scott Ingram: Yeah. And I mean, good on you for acknowledging it and reaching out and asking for the help. Cause I think the real trap for most of us, and I'm raising my hand here, Is I'm like, oh, I'm in this place. I don't want to expose myself. And we go through it by ourselves and we probably stay down longer because we're not willing to acknowledge and say, you know what? I am just not with it. I need some help. Who can help me? And amazing that you have that manager. We're going to find that LinkedIn post. So if you go to top1.fm/184, I actually know my number for once. Or if you go to top1.fm/morgan-cumiskey, so you can do that with any of our episodes. You'll find all of our show notes. We'll have that post linked up so that you can check that out. You can connect with Morgan, do all the good stuff. Morgan, let's really now dig deep into just all of the habits and routines and the way you structure your day and maybe just walk us through a day in the life. So your alarm clock goes off. What time does that happen? And just walk us through the whole process until your head hits that pillow again.

42:07 Morgan Cumiskey: Yeah. So I am one of those crazy people that has a 5:00 AM alarm every single day. I used to not be that way. When I first started in sales, I was one of those people who I would wake up at 7, 8 o'clock. I would get right on my computer. I would stress myself out immediately because I would take just no time to myself in the mornings to really get my head in the right place. I have a Hatch alarm clock. If you don't have one of those, this is not a Hatch plug, but you actually should invest in one. It wakes you up with like birds chirping and a sunrise. So it wakes you up very naturally. So it's less of like an alarm clock. Alarming jar of waking up. So I get up every day with my Hatch. It mimics the sunrise and I wake up very peacefully. I try to… first thing when I do when I get up is not check my phone. So I try to stay off my phone for at least the first 30 minutes. There's really nothing on my phone that needs my attention at 5 in the morning anyways. Those emails can typically wait. I try to do at least 10 to 15 minutes of meditation. I journal. I try to get outside. I've got a dog, so I try to get some fresh air before I know I'm going to be behind my computer screen all day. I get a good breakfast and then typically my morning routine really starts with the night before. Every single night before I go to bed, I'm blocking off my calendar with the things that I know that I need to do. It's a major red flag for me if I have a completely open calendar day. So if I log in the next day and there's nothing on my calendar and they don't even have to be meetings, that's a red flag for me. Even the night before I'm going in, I'm kind of doing an inventory overview of my day and then I'm looking at, okay, now what can I do tomorrow to set myself up for success? And if I don't have any demos, I'm blocking an hour or 2 for prospecting. And I'm not just putting it as a prospecting block. I'm doing it as a prospecting block with these specific accounts or this specific strategy. So maybe I'll do LinkedIn for an hour. Maybe my second hour of the day will be calls. So I make sure that I'm in my blocks, making sure that they're as detailed as possible. So I have to go into them, make myself accountable, actually do the tasks. So when I log into my computer every single day, I kind of already know what the day is going to look like. Typically, I try to watch a Gong call every single morning. I have a 30-minute block first thing in the morning that I try to watch somebody's Gong call. And whether that's just a seller that I really like the way they sell, or whether it's like a, hey, I got asked this question about something related to our product that I didn't know, I'm going to go research that for the first 30 minutes of the day. So when my mind is at its freshest, I try to take in some information, maybe read a couple articles, but it's mostly 30 minutes of learning every single morning. From there, I typically will have 1 to 2, maybe 3 demos. So those are 45 minutes long each, 2 prospecting blocks in between those demos. And then I usually have a 45-minute block at the end of my day to take care of everything that came up during the day. I have my calendar blocked out. Obviously I want to make sure that I'm completing those things, but things will come up throughout the days. You have deals that are in flight. You have prospects who probably need things from you. So I always try to make sure that I leave like a 45-minute to an hour-long block at the very end of my day. To do the things that maybe came up on my plate that I didn't have time to get to.

45:05 Scott Ingram: I want to stop you right there because that's really interesting. So you basically… I'm going to call it a deal with it block. Instead of being interrupted by all of this stuff that's going to come up or knowing that I've got all this follow-up I need to do after these calls, you basically have time already set and you just dump it into that spot so it doesn't have to haunt you. You're like, You will be dealt with, but you're gonna be dealt with over there, not in the middle of, I'm prospecting now, I'm doing this demo now. Am I getting this?

45:33 Morgan Cumiskey: Oh, exactly. I mean, it's such a hard thing to do to focus on one task at a time. I mean, if I'm not on do not disturb when I'm trying to make cold calls, I'm getting Slacks from people, I'm getting emails, I'm getting messages back from LinkedIn that I've sent out that morning. So when I'm prospecting, I'm only prospecting. When I'm on my demos, I'm only doing my demos. And when I'm answering emails, I'm only answering emails. So it's worked well for me to try to get into a frame of mind of like, hey, this is the task I'm doing for 45 minutes and nothing is gonna take my attention. The word multitasking is actually a total facade. The human brain actually can't multitask. We can only focus on one thing at a time. When you're multitasking, your brain is just switching back and forth at hyper speed between an email and a text or an email and something else. Really hyper-focusing on what I'm doing has allowed me to be more productive in that block of time. And then at the end of the day, my deal with it, I like that you called it that, my deal with it block, I'll deal with everything that came up during the day versus it taking my attention because I'm just not going to be productive if I'm trying to make calls or doing demo follow-ups and trying to do a million different things at one time while I'm also dealing with everything that got thrown on my plate that same day. So being able to clean that up at the end of the day has been really impactful for me.

46:46 Scott Ingram: I love that. I love that. What do you call your block? I invented deal with it, but do you have a name for that thing?

46:51 Morgan Cumiskey: It just says do not book. So people know do not book block. It's just just blocked off so no SDRs or anyone knows this is my time to lock in and finish up the day, put a bow on it, and then set myself up for tomorrow.

47:06 Scott Ingram: Such a brilliant approach. And so that is also when you're doing that work of kind of blocking out your next day that you described?

47:13 Morgan Cumiskey: Yeah, exactly. Sometimes I'll do it at that block. Sometimes I'll do it right before I go to bed. I try to always, and I know this is probably a hot take, but I try to always do a little bit on a Sunday too, sometimes between like Friday and Sunday, your brain can just go in a million different directions. So I do end up taking like an hour, like Sunday mornings usually, or Sunday afternoons, and just saying like, hey, what do I need to get done this week? It's the biggest anxiety trigger for me to open up my, my computer on a Monday morning and not have opened it at all and set myself up for success for the week. And it doesn't have to be this massive block, but take the 30 minutes, get an idea of what your week looks like. Who are you talking to? Maybe even write out A few questions that you want to ask the specific deals that you're going to be getting some actual video time with. But yeah, the do not disturb block, no notifications, phone is face down. I'm locked in.

48:00 Scott Ingram: Love it. I'm a total productivity freak. There's some good nuggets in here for sure. But I also think the things that you're doing where you've got a daily time that you're like, let me be strategic and thoughtful about how I make the most of tomorrow and what I need to deal with. And similarly, sort of that weekly thing, I think what it does is it just takes psychic stress off of you. Like if you don't have that plan, you just have all these things that haunt you, freaking gremlins in your head. You know, like I can't enjoy the weekend while these things are bugging me. And if I just, hey, look, I'll deal with you, then they'll go away.

48:33 Morgan Cumiskey: 100%. Just being like hyper-organized in your business just takes so much of the sales anxiety off of your plate. And we already deal with so much anxiety as sellers and stress and hitting numbers and quotas. You're back to zero again. And it's like, how can you reduce the most amount of that as possible is just to have a plan. Like have a plan, know what you're going to do, go in and execute it, make no excuses, be productive and say the things that you say you're going to do or do the things you say you're going to do. A lot of that stress goes away. You could be a really good seller and be so unorganized and you are going to feel so much more stress. And you could be like a mid-range seller and just be hyper-organized. And I guarantee You're going to find so much success in the way that you operate and the way that you feel showing up to work every single day. That always articulates to how you show up to your customers. If I show up to a Monday morning meeting and I haven't prepped for that call the night before, I look stressed, I feel stressed, my customer, my prospect can tell that I haven't prepared. So just take the 5 to 10 minutes, prepare for the next day, prepare for the next week. You'll find that you will be showing up in a way better mindset to your conversations, and that'll make you a better seller in the long run.

49:45 Scott Ingram: Such good stuff. I know you've touched on a lot of these, but are there any other kind of habits or routines that you incorporate throughout your day that are kind of central to your success?

49:55 Morgan Cumiskey: Yeah, I mean, I think one of the things that has helped me a lot in my success beyond the calendar blocking, beyond like all the mindset things that I'm doing, beyond the Gong calls is I always try to make sure that I'm communicating with my teammates and my leaders. I know we've always kind of talked about being in a remote world, like not having those internal relationships can really kind of get you in a spot where you're feeling very isolated. So I always try to make sure I do spend a little bit of time throughout the day just checking in on my teammates, saying hi to everybody. Obviously we're here to work, but you do want to make sure that you're giving yourself a little bit of time to be able to, number one, like you mentioned, ask for help if you need it, but then make sure that you're taking the time to just build relationships with people in your organization. One of the first conversations that we had, Scott, was like, hey, when new people come to your company, like, are you reaching out? And making sure that number one, you put a face with the name. Those people that are coming inbound or coming into your organization, like they're feeling the same things that you felt when you started. So making sure that you're reaching out to them, building those relationships, and And that will only be more fruitful for you in the future. Like, let's say they leave your organization and they're doing all these cool things. Like, those are relationships that you could have in the future. So always like taking time to just like, hey, I'm going to check in with my people. I'm going to make sure that everyone's all good. I'm going to ask if anyone needs anything. I'm just kind of going that extra mile to, yes, do the work, block your calendar. You're there to work, like get into grind mode, but don't be afraid to like have a little fun throughout the day. Throw 15 minutes on your teammate's calendar and say, hey, I just want to talk. I just want to chit-chat. Take the time to have a little bit of fun with it because we can be very serious at work all the time. But yeah, build relationships with your people, like have fun. Don't take it too seriously. So I always try to do that too.

51:40 Scott Ingram: Yeah, that's awesome. I know one of the things we talked about early on was I recorded a Daily Sales Tip not too long ago about being a one-on-one meeting machine. And it was really initially in the context of, oh, you're starting in a new role and you need to build all of these relationships because all of those people are core to your future success. But the conversation you and I had was that should never stop. You should always be doing that. And when you're in a fast-growing organization, there's new people joining all the time. And this is also a very long-term play because having ridden a couple of those kinds of IPO-type rocket ships, that's your future network. Those people are going to go off and do amazing things, and you want to have those relationships. You want to be connected to them because you never know, there's going to be some future thing there's an executive opportunity for you because of that relationship that you have. So such good stuff. Let's talk about your information diet. Besides the Gong calls, what are you listening to, reading, watching, and when does that happen?

52:37 Morgan Cumiskey: Yeah, yeah, that's a really good question. So I always try to ingest articles about what's happening in the industry. We actually have a Slack channel here internally that we have a team that will actually just drop the latest news about what's going on in our industry, what's going on in our customers. So I watch that like a hawk and I'm always trying to understand what are some of the biggest pain points that our customers might be experiencing in the cybersecurity space and then how are we solving for them. So it comes from a number of different blog posts. Sometimes it comes from like Forbes or other articles that are just online, but we have a really strong Slack channel that just drops latest blog posts in that. And I try to always spend either during that Gong block, if I'm finished up with a Gong, I'll try to go and read a couple of articles and just get myself acquainted with what's going on in the industry. And then you can bring some of those data points to your conversations. There was one that I think it was like a 2023 compliance trends report that got released last year, and there were so many good data points in that blog that I took to every single conversation that I had. Moving forward. It was like 80% of companies who don't invest in some sort of continuous compliance are receiving negative impacts because of X, Y, and Z. And if you can show up to those conversations as like a thought leader and actually bring like, hey, I saw this blog post and this is what it said and this is how it could impact you, it makes you look like an industry expert. So you can even go and try to find, sometimes there's groups that you can join. I'm in a couple of Slack channels for compliance. I'm based in Nashville, so I'm part of a Nashville-based cybersecurity Facebook group, and I'm just watching what people are saying. I'm trying to see like what are the trends. I'm asking questions about what they're seeing. So I think groups are, you know, Facebook groups, if you can get into them. Sometimes there's, as silly as it sounds, like Reddit forums are really, really cool. People speak their mind on Reddit. So if you can find a good Reddit forum that is accompanied with the industry that you work within and just read what people are saying, you can get some really good insights into what's going on.

54:33 Scott Ingram: Awesome. Awesome. Awesome. We've talked about Salesforce and Slack and Gong. What are some of the other just tools and apps that are core to your functioning?

54:41 Morgan Cumiskey: Yeah. I mean, as a salesperson, we've got so many different apps that we use here internally. I would say one of the ones that is really, really strong at my company in particular is an app called Crossbeam. And I'm not sure if you've ever heard of them, but they, and it goes back to the way that I like to manage my business in terms of of partners, but when I log into Salesforce every single day, it's one of the first things that I look at is Crossbeam. And what Crossbeam does for us is it identifies if we have any vendor relationships or partner relationships with that particular prospect. So I know like, hey, I log in, this is a target account for me. I check Crossbeam. I see if they have an existing relationship with maybe one of our resellers or MSSPs, then I can immediately go to that reseller or MSSP or service partner, whatever the case is. Ask more information about the account, see if they'd be a good fit, maybe even ask for an introduction. That's one of the things that I rely on pretty much every single day to keep my pipeline strong with Crossbeam. We also use a lot of tools like ZoomInfo and Seamless. One that we recently invested in is a tool called Nooks. I don't know if you've heard of them. It's like almost like a speed dialer for cold calling. Less impactful necessarily for me, but my SDR uses it every single day and absolutely Awesome.

55:51 Scott Ingram: Good, good, good set of stuff. And for those that aren't familiar with Crossbeam, it's basically a way that organizations can share their Salesforce data between them without giving access. So you can kind of see, oh, this partner of ours has this company as a prospect, or they have an open opportunity, or they closed a deal with them 6 months ago or whatever it is. So yeah, absolutely powerful tool. Morgan, do you subscribe to a particular sales philosophy?

56:17 Morgan Cumiskey: Not necessarily a particular sales philosophy. I've read a lot on the Challenger Method. I think if I had to subscribe to one, that would probably be the one that I would relate to most closely is the Challenger and just being able to not take anything for an answer and always go a layer deeper. I think your customers, especially in this day and age where they're just constantly being sold to, really appreciate when people do take the extra time and challenge their thinking. How many times have we gotten into conversations as sellers where buyers will show up and they think that they know everything about you and about your product and about what you do and the way that they do things is the way that they do things and being able to challenge the status quo and ask those questions to get them to unpack like, hey, I know you're doing this the way that you are today, but what if you did it like this? So I think if I had to subscribe to one or align to one, that would probably be it. But I think along the way I've kind of developed my own personal flair of of that. So yeah.

57:13 Scott Ingram: Yeah. Let's lean into that. I mean, how would you describe your personal flair or your style?

57:18 Morgan Cumiskey: I think my personal flair and style is obviously challenging. I always try to show up to conversations and, and curious. I think that's probably the word that I resonate the most with is just like curiosity. I'm never afraid to say that I don't know something. If prospect asks me a question and I'm like, hey, I've never heard it done that way. Can you tell me why? I'm always just trying to be constantly curious and more curious to learn and never afraid to fall on the sword if I don't know something. So I think my personal style is just being very open with my prospects. I try not to ever be too pushy, but just hyper-curious about why they're doing the things that they are. What impact does that have on their business? If they did things differently, if they did things this way, how would that work for them? So just being hyper-curious in a way that is authentic to customers too, and just showing up and being your true self. I always try to take the time at the beginning of the calls to just build that initial rapport. People are being asked about the weather every single day when they get on with calls, like, hey, where do you live? What's the weather like? Go the extra step, look at their LinkedIn, find out where they went to college, try to be authentic in the way that you show up. They'll remember those conversations. I think it's like, for me, I feel like the conversation went well if A, obviously the call went well and we did good discovery and they're a good fit, I learned something about my prospect. I learned if they have kids, I learned where they went to college, I learned what they like to do on the weekends. That only helps build and nurture those relationships. So just being authentically yourself and not coming off too cold, I think, has really been the way that I've tried to sculpt my personal style. When people get off a call with me, I know something about them, they probably know something about me, and I ask them about it on the next conversation. Like, I learned that maybe they were doing something with their kids over the weekend. I always make note of that and I follow up. And that also helps me differentiate myself against competitors that might not be doing that. They know when they talk to Morgan, I'm going to ask questions about their kids or whatever the case is, what they like to do, if they have hobbies versus if they show up with one of our competitors and they've only talked about product. It's just going to make me more memorable. So I always try to show up and just be authentic and have a laugh and try to not make things so cold all the time. We can get into that cycle in sales to just show up and be robotic. So just show up. I try to be myself. I try to crack a couple jokes here and there, keep things light, be memorable, and yeah, just be me.

59:34 Scott Ingram: Yeah. So good. And I experienced this with you. We got on our first call and you had done enough research to recognize, oh, you have also worked with some very fast-growing organizations and have been through this IPO journey. And what can you share with me about that experience? And we had some great conversations just based on that. And to me, that is such an important differentiator, just showing that you've done just that little bit of research and you can ask an intelligent question that's about them and coming from a place of genuine curiosity. I'm interested in understanding this. Talk about that. And there's some background, there's some story that was coming from that, right?

1:00:10 Morgan Cumiskey: Yeah, exactly. It's just showing up and caring. Your prospects may have had 6 conversations exactly like yours. So if you can show up and show that you care, even like you said, that 5 extra minutes, that 5% of your energy and effort that just spending on caring a little bit more, It makes it really memorable and you can build those relationships out into the future. They may not buy from you, but they may have really liked you as a salesperson. I've had a lot of deals come back to me that were closed lost, but the person that I worked with got so much value and enjoyed working with me so much that they referred me to their friend who also has a company, has needs that we can solve for. So just making sure that, you know, the person on the other end of the phone is also a person with a life when they shut the computer. They have to go deal with their life too. So just be genuinely curious. Talk less about you, talk less about your company, talk less about yourself and what you can do for them and let them lead. Ask them questions when they're talking, let them talk and always go a layer deeper and trying to understand the why.

1:01:07 Scott Ingram: Yeah. So good. Well, speaking of the why, what drives all of this? What motivates you? How do you think about motivation in general?

1:01:15 Morgan Cumiskey: Yes, I think it's for me less about motivation and it's more about discipline. I don't wake up every single day ready to make cold calls or do demos. Like some days, yes, like I love what I do. I'm very passionate about sales, but I think for me it's more about the discipline side of the house and making sure that if I say that I'm going to do something, that I do it and I do the activities to get me to the result that I want. But from a motivation perspective and kind of what gets me up in the morning, I really do love of the culture of nurturing relationships, helping younger sellers. I wish that when I was a seller, I had, number one, more people to look up to, but specifically like more women in the space that were talking about how to sell as a woman, how to ask questions differently than maybe some of our male counterparts. It's motivating to me to be in a position now at my company where I can actually be making an impact on some of the younger sellers who are coming into the business, some SDRs who are really looking to accelerate their career. So that's really motivating to me to know that they can look up to me in that way. And now that I've been in sales for a couple years, like, I do have some knowledge to share. It's more about being disciplined in what I'm doing and the activities that I'm setting out for myself and making sure that if I'm writing a goal, that I'm gonna hit that goal and I'm gonna check off the boxes every single day and I'm gonna do the 100 calls if I say I'm going to do the 100 calls and just making sure that I'm relentlessly disciplined in everything that I do.

1:02:45 Scott Ingram: Awesome. Awesome. What are some of those things as a successful woman in sales that you wish that you had known or heard that maybe you just don't see and hear out there enough that the women listening to this can draw on?

1:02:59 Morgan Cumiskey: Yeah, I think it's such an important topic and I didn't really realize it until maybe like 2 years ago that every single for the most part that I was seeing, every single course or every single tip that I was seeing was from a male perspective. And obviously sales in general is somewhat of a male-dominated industry. So you have to kind of come into it knowing that. But what I started to realize was there were so many skills that women have by nature that we're not taught how to harness every single day. Women are naturally more empathetic. We naturally have more active listening skills. We're natural problem solvers. There was nothing out there that really taught me how to sell and harness some of those skills in ways that would accelerate my career. I wish that there would've been something that says like, hey, here's how you do discovery, but here's how you can ask questions in a way that you can harness your empathetic mindset or your problem-solving mindset and lead in being a woman. It's something that I'm really passionate about, something that I'm actively working on making more space for. I've seen it start to trickle down. I'm seeing more and more of it every single day. It makes me so stoked to be someone in this space that will hopefully have a voice to teach younger women to not only harness what they naturally have ability-wise, but also as a space in a community for us to kind of get together and lean on each other. I think something that I hear so commonly in just women in sales is like, hey, sometimes it feels like a boys' club. When you look at sales orgs across Typically it's male dominated. Creating a space for women to get together, share their insights, just lean on each other, but then harness some of those skills I think is really, really important. Something I'm super passionate about.

1:04:40 Scott Ingram: Yeah, such good stuff. I hope that you continue to put that stuff out there, whether it be on LinkedIn, whether we start to feature you on Daily Sales Tips. Something I'm passionate about. I think there needs to be more women in sales. Frankly, I think women are better sellers because of many of the reasons you described. And now my youngest daughter is very interested. In a sales career, right? So this is a very full circle thing for me. I think it's a really important issue and I want to make continued feature incredible women with incredible stories, both on the show, at the Sales Success Summit, inside the Sales Success Society. So if you're one of these people, if you're like Morgan and you find yourself at the top of the leaderboard and you are a wildly successful woman in sales, or that person is on your team, would you please reach out or get them connected with me so we can continue to feature these stories because this is important. I think we all need to hear these stories and the men do too. There are things that we can learn from women. There are things that we need to be aware of when we're working with or leading or working for women that are just important that I think we need to be more mindful of. And there's an opportunity for all of us to be more successful if we let that happen.

1:05:48 Morgan Cumiskey: Yeah, absolutely. I think it's important to bridge the gap. Like there are so many things that I've learned along the way and a lot of the leaders that I've looked up to in my life have, have been male and some of them have been women and I've learned different things from both of them. And just having that clear balance and understanding, I think just makes you a better seller. At the end of the day, there's things that we can learn from both of each other, but just creating the space for women to have more of a voice and a seat at the table. I'm seeing at my company specifically, a lot of the top performers are women. So it's really cool to see the culture that we've harnessed here. And just be surrounded by really, really, really strong-minded and really successful people.

1:06:22 Scott Ingram: Love to see that. Love to see that. Morgan, is there something that the average or typical salesperson believes, or just part of the sales dogma that you think is nuts? Everybody in sales thinks this thing and you're like, that's wrong.

1:06:38 Morgan Cumiskey: Yeah, I think I do have one and I think it's changed over the years. I think Nowadays, sellers today think that being in person is kind of like a dead breed. I think we've all gotten very comfortable being behind a computer screen and doing things virtually. And recently I have, and I used to be one of those sellers. I was a firm believer in, okay, I can do what I need to do from Zoom. And the in-person touch is not as meaningful as it used to be because everyone works from home and COVID happened and this and that. And I proved myself wrong this year. I have started to take more time to get onsite with a lot of my prospects, and I'm very fortunate that I work at a company that allows me to do that. But yeah, getting in person with people is not a dead breed. It really does make a difference. I had one of my first offsite meetings. I used to go offsite a lot more at my last company I was at, and I did one of my first ones here at Drata. And number one, I left that just feeling so rejuvenated. You get so just in your groove of being behind a computer screen and not interacting with people. We talked 90% about just random things and 10% about Drata. And I felt so rejuvenated leaving that conversation in general as a seller, because I was like, wow, this is really a relationship that I'm going to have and cultivate. And it's going to help me show up better to our conversations now that I've shook this person's hand and we had brunch together. So it's something that I think a lot of salespeople kind of turn their nose up to nowadays is like, hey, I don't need to go see this person live. But yeah, shaking hands with people is so important. Again, I've proved myself wrong. I used to be one of those people, so I can't speak too deep about it. But yeah, getting in person with people is so important. It really differentiates you as a seller and helps you build deeper relationships, helps you learn about them and who they are as a business. It helps you ask questions and they can't hide behind a computer screen. I know how frustrating it can be as a seller to get on a Zoom call and Sometimes the person won't even turn their camera on and you're like, I've never seen this person's face. And that's a red flag for me in a deal. If I've never seen the person's face, no matter how good the deal is going, that's a red flag. If you can get in person with people and they agree to see you, obviously if you have like a territory that's regionalized to you and you can even get in your car and drive a couple hours and drop somebody off a box of cookies or just offer to take them to coffee, those things can go a really long way. And I think a lot of people nowadays are just really really comfortable in their little Zoom bubbles. And I'm comfortable in my Zoom bubble too. But yeah, getting in person with people, I think that's probably a hot take.

1:09:02 Scott Ingram: Yeah, that's wild. I mean, what a full circle thing. I mean, I've been selling for a long time. This was the standard. And I think before COVID people would have said, oh my God, it's crazy that you could think that you could sell 100% virtually. And now we're on the other side of that. And I think you're so right. Imagine a deal where you and your competitors, I mean, you're all having these conversations, you're all on Zoom, but you've actually met them. You actually spent time with them. You broke bread. There's magic. I've always felt this way when you go visit somebody. It has the real power in that has nothing to do with the meeting. It has to do with what happens in the hallway and over coffee and at lunch when we have the real conversations and so little of that, that just really, really human to human stuff doesn't really happen over Zoom. There isn't that just natural transition space. Like we're in the meeting. I've got a hard stop. I got to get to the next one. Like we just don't get to really connect human to human the way that you do when you're walking to the conference room or you just finished the meeting and everybody's kind of walked away and they're like, okay, yeah, let me give you a little bit of the lay of the land here. Did you notice this? Did you see that? Just all those little things.

1:10:13 Morgan Cumiskey: 100%. And it allows you to have space to speak freely with your prospect one-on-one. A lot of the times that you're coming to these meetings their boss is on the meeting too, or maybe their colleague is on the call and they may not be comfortable sharing with you what they would share with you if you had them one-on-one. And what better way to do that than to take them the coffee or take them to dinner or even just show up at their office, obviously with their permission, to get them in person. They feel almost not like they owe you something, but it makes it easier for them to want to work with you. And hey, this person took time out of their day, out of their week to come and Take me to dinner, take me to coffee, and they're just more open to sharing information. They're more open to bringing you to the executive buyer if they haven't done that already, because you took the time, you went the extra mile, and it just shows that you're showing up and that you care about them as a person. And they're just more willing to give you the information that you need to progress the deal in a way that it should go. It happened recently with me. I was working a deal, a competitive deal that we were getting kind of cold feet from the prospect. And I was starting to get some red flags and I was like, you know what, I'm just gonna get on a plane and go see this person. And I did that. And since that has happened, she has not gone more than a day without answering emails. She is bringing us to the CTO and the CISO who are the executive buyers in the deal. We are moving forward with legal. And before that, I was getting major red flags. I was slacking my manager saying like, hey, I don't know if we're gonna get this deal. And by going in person with her and just getting to know her as a person, And building that relationship, I think we're probably going to get a closed one in November. So it works. And again, Zoom bubbles and all that is still so relevant. And I think even more now after COVID, no one is doing it. So if you do it, if you're the one out of your competitors that are showing up in person or even just like dropping off like a box of cookies, you are going to make yourself stand out and it can only benefit you.

1:12:07 Scott Ingram: It's killing me because I can't remember who it was. I'm going to find it. We're going to put it in the show notes. So again, top1.fm/184. I'm going to fix my problem in post. But I had a conversation with somebody and their whole approach was, even if you can't do this in person, they would work to get one-on-one with every stakeholder in all of their deal cycles for exactly this reason. There's so many of just those things where I can start to build that personal relationship a little bit more, but I can also get to what do you care about? What is the thing that you're uncomfortable talking about in front of your boss or in front of your peer, but it's really important for me to understand in what's going to make this connect or have value for you. And if you can wire your deals in that way, oh my gosh, are you going to win.

1:12:54 Morgan Cumiskey: Oh, 100%. 100%. If I have a group demo, if the first call that I have with somebody includes 2, 3, 4 people, I always make it a part of my process to reach out to those individuals in particular, just off one-on-one thread. You send your follow-up with everybody on that, but I always try to reach out one-on-one. Either it's LinkedIn, I'll send them an email and say, hey, this is what I heard that you cared about. Did I get that right? Am I missing anything? Let's grab 10 minutes because I know that during that 45-minute-long call, you only got 5 minutes to talk about what was important to you. And I'm sure it doesn't stop there. I want to make sure that I can support you and what you care about and grab 10 minutes with them. You very easily will find that the person that you thought was not an influencer in your deal is a huge influencer in your deal. And sometimes that person can also be, we call them like an enemy in the deal. So the person that you didn't talk to is the person that when you get off the call, they're saying, we don't need this, this isn't working. And they may be and have way bigger influence than you thought. So just unturn that stone, ask them for the time, figure out what's important to them. It'll only help you and it will hurt you if you don't do it. It can come back and bite you. You'd be surprised. You can get on a call and X, Y, and Z, and you're like, wow, I forgot that they were even part of this deal, like said that we didn't need this. And you're like, wow, I didn't take the time to really figure that out. So yeah, turn those stones over, talk to people, get one-on-one time, get their cell phone numbers if you can, get on a texting basis with them. But yeah, if you can get on Zoom, a Zoom call, quick 15 minutes, it'll be really beneficial.

1:14:19 Scott Ingram: Yeah, that's awesome. Morgan, are there decisions you've had to make or lessons you had to learn to really break through and get to where you are today?

1:14:28 Morgan Cumiskey: Yeah, I think one of the things that I had to learn early on was not to fit a square peg into a round hole. I wanted to win every single opportunity as most hungry salespeople do, and I had to learn to really get good at qualification and disqualification. I think there's so much content out there in sales trainings around how to qualify, but every single call that I get on now, I'm looking for how do I unqualify this deal? How is this person not going to be a good fit? And I make sure that I'm very, very confident in the fact that I'm chasing seals and not surfboards. I'm spending my time where it's best spent, but I'm trying to unqualify deals as fast and as quick as possible to make sure that my time is well spent. So when I first became a seller, I wanted to win every single deal. I tried to make people's problems fit into what we could solve for. That number one got me into a lot of very complex sales cycles where my customer success team was not super happy with a deal that maybe just closed that wasn't a great fit for what we do. It wasn't a great experience for the buyer because I felt like I was pushing them in a direction that they just didn't want to go in. So now what I try to do is show up and unqualify those deals as fast as possible just to make sure like, hey, this is a good fit for what we do. We are going to be able to solve the problems that they have. This is going to be a good good experience for them when they're handed over to CS. And I'm not wasting my time on deals or organizations that are just not ready or not good fits for what we do. And going back to that abundance mindset, yes, they're not a good fit, but there's a million companies out there that you can go dial on or call on to backfill for it. So yeah, just being okay with losing a deal, unqualifying a deal, not holding on to things for multiple quarters at a time. I think as a seller, we all probably do that. You've got a couple dusty deals your pipeline that probably shouldn't be in there, just unqualify them, let them go, make the space in your head for something that's a better fit. People not wanting to move forward, like that's a negative buying signal. Push those deals out, close them out. You'll get to them in another quarter.

1:16:28 Scott Ingram: Yeah. I really wish this was something that we put more emphasis on because I think it makes for much healthier businesses and hell, it makes us healthier if you really focus on… I love the idea of just disqualify harder. Really understand that because when you bring in unnatural deals, they're not good for the business. You've got an unhappy customer, they're going to churn, they're going to leave a negative review, they're going to talk bad about you versus what if instead you have a reputation of just being a straight shooter and people feel comfortable reaching out going, look, I'm going to ask Morgan about this. I know she's not going to sell me. I know I'm going to get a straight answer and she'll tell me the truth.

1:17:06 Morgan Cumiskey: Exactly. Don't be afraid to walk away from deals if it's not a good fit. If you know that in your heart you're going to pass this deal over to CS and this customer is not going to be extremely happy with what you're doing, like, don't be afraid to walk away. Your customer will respect you for it and they may even come back to the table 6 months when you can solve their problems versus, as you mentioned, you bring it on the customer, them leaving a negative review, then you have to deal with your competitors throwing that in your face on a call. Call. Like you never want to be that person and you don't want to burn bridges with customers either. You never know who you're selling to. You never know what relationships they may have or what their work looks like. And just always try to never burn the bridge. Walk away if you need to. Your business will respect you for it. You'll have more integrity by doing that. Your customer will respect you for it. Just don't be afraid to walk away if you need to.

1:17:53 Scott Ingram: So we have to go back to something because I think you hit me with a shark reference. Did you say seals, not surfboards? What was that?

1:18:01 Morgan Cumiskey: Yeah. So my CRO at one of our sales kickoffs was talking about the method of unqualifying deals. It's something that we do over here at Drata is like, make sure that you're walking away, unqualify them as fast as you can. And one of the references that he said was make sure you're chasing seals and not surfboards. So if you imagine yourself as a shark, if you're down there swimming at the bottom and you see a shadow up at the top, make sure it's a seal before you go and take a bite out of it. You're expending energy when you speed up to the top of the wave and have to jump and breach out of the water to catch it. So better make sure that you're chasing seals and not surfboards. It's a very silly analogy, but it's one that stuck in my head for a few years and I really like it. So I love it.

1:18:39 Scott Ingram: I love it because one of those is made out of meat and the other one is like fiberglass or something that you really don't want to eat.

1:18:45 Morgan Cumiskey: Yeah, exactly. Cardboard. It's not going to taste good. Not good for anybody. So yeah, I'm an analogy person. For some reason, those things always stick in my brain. I don't even live by the beach, so I don't know why that one resonates so much with me, but it does.

1:18:58 Scott Ingram: That's fantastic. That's fantastic. Morgan, what advice would you give to somebody that is just starting out in their sales career today?

1:19:05 Morgan Cumiskey: It's going to be okay. It's going to be fine. But no, I think just being open with taking everything in that you can related to, like I said, your industry, making sure that you're finding one or two people that you really resonate Try not to get overwhelmed with the product that you're working to sell. I see a lot of very young sales folks come into their careers and all they want to do is learn the product, learn the product, learn the product. Slow down, take a step back, get to understand the problems that you're going to be solving for the people that you're going to be selling to. Take the time to reach out to your customer base and talk to them and get a clear understanding of why they bought your product. Take the time to reach out to people at your organization and talk with them about what they're seeing and what they're doing. Care way less, so much less about your product and what you do. Take all that focus off of you and yourself and care more about the problems that you're solving and the people that you're going to be selling to.

1:20:00 Scott Ingram: Awesome. Awesome. Awesome. I know we've probably touched on this a little bit from different angles, but I still want to ask the question again, which is, let's imagine you're a little further into your career. You're doing well, you're doing okay, but you're not great. Like you haven't found that gear that's going to put you to the top of the leaderboard. What do you tell that person?

1:20:18 Morgan Cumiskey: I think it's so common for people to be in sales for 1, 2, 3 years and really not meeting the milestones that they set out for themselves. So I think that I would ask that person, what are you doing well? What are some of the things that you think you can improve upon? And what are the top performers at your company doing differently than you? Like you said, it's very hard as a seller to ask for help sometimes, but every company that exists, there's people who are at the top. There's people who are 1, 2, and 3. Don't be afraid to go and ask them what's working for you. What questions are they asking that you're not asking? Can you go and watch some of their calls, like watch their deals and how they flow? And don't be afraid to go and try to embody what some of those top performers are doing. Get out of your head and lose the ego a little bit and say, hey, I know that I can be better. What are some of the people at my organization that are where I want to be? What activities are they doing? What does their day-to-day look like? Like, what do their calendars look like? How do they structure their demo or their discos? Just get to know kind of that and try to embody that and not be afraid and humble enough to ask. It's something that I did when I came to Drata. There was a few sellers that were just consistently at the top of the leaderboard, like quarter over quarter, just absolutely crushing their goals. And I mimicked exactly what they did. It wasn't anything that I did rocket science-wise, but I was like, hey, they're number one and I want to be number one. So What are they doing really well? And every single company has those people, so just don't be afraid to ask.

1:21:40 Scott Ingram: Yeah, fantastic. Which is a perfect transition because I also like to ask, when you get to number 1, you no longer have that person to ask, okay, how do I go to this next level? So what's the question that you have of top sellers in other organizations?

1:21:54 Morgan Cumiskey: Yeah, that's a good question. And yeah, of course, when you're at the top of the leaderboard, I always still take the time to understand and realize and be humble enough to know everyone that works at my company is an outstanding seller. I can learn something every single day. If I were to go and ask like a top performer at another company, like I'd want to know what their day looks like versus my day. What are some of the activities that they're doing? Like, how are you finding net new opportunities within your existing territories? And maybe I can articulate and do some of those myself, but I'd want to know mostly about what their day-to-day looks like. What are some of the ways that they're asking questions? Maybe some of the ways that I can enhance some of the ways that I'm asking questions. But yeah, just kind of learning about what their day-to-day looks like, how they stay in a good mindset, how they're finding net new deals, and kind of trying to transition that into what I'm doing here.

1:22:41 Scott Ingram: Nice. Nice. Let's go back to, I mean, you're still relatively early in your career. What are the open questions that you have from successful women in sales who are further into their career?

1:22:52 Morgan Cumiskey: Yeah, that's a good question. I would ask a successful woman who's a bit further in their career, like, how did you keep the grit and the mindset that you have. I think one of the things that I struggle and struggled with a lot when I was first entering into sales, and I still feel like I struggle with somewhat in a day-to-day basis, is just like, number one, keeping my mind right. A lot of what I do and everything that I do in my sales career and the way that I structure my days and how I wake up in the morning is all kind of based on like a specific mentality. And I think being a woman in sales, especially when you get to that manager position and that executive level position and that VP level position, you see it more commonly that you're surrounded by men. And I would personally like to know, like, how did you stay with the path? What are some of the things that you would tell yourself every single morning when you would get up to know that, hey, I belong here? How do you find that sense of belonging when you don't see many people that are like you? And just kind of understand how and why they found one person or maybe multiple people that they saw that they tried to get mentorship from? What are some of the ways that they did that?

1:23:58 Scott Ingram: Love it. Love it. Great questions. Great, great ideas. We've covered a lot of ground. We talked about a lot of great stuff. Is there anything that you were hoping to talk about that I just didn't ask the right question or we didn't get to?

1:24:11 Morgan Cumiskey: I think you covered a lot of it, Scott. I would say like the only thing that I would have loved that we talked more about is just kind of like culture at companies. I think that's one of the things is so important is like, hey, we show up every single day and we do this job, but how can we make sure as sellers that we are showing up and actually providing benefit and being a part of the culture? Obviously sales is a one-person job. It's also a team mentality. Like, what are some of the ways that you can make sure that you are participating in your company's culture as a seller?

1:24:43 Scott Ingram: Let's talk about that. I love this topic. This is totally, you're pushing buttons buttons for me. What's your perspective? However you want to tackle that. And then I'll let you ask me a question and we'll go from there.

1:24:53 Morgan Cumiskey: Yeah, I think culture is so important. And I think sometimes as a seller, you can get into a little bubble of feeling like you don't have to participate in the culture because you kind of own your business and you've got your deals and you're just closing and getting into that mindset. I think culture is so important for a number of different reasons, but I think one of the biggest things sticks out to me is just making sure that you feel comfortable in this space to number one, ask for help, that you feel comfortable in where your career is progressing. Hey, if I work at a company where I don't feel comfortable or the culture isn't there, it's not what I want it to be like, am I comfortable enough to be taking a leadership position at the company and making sure that you're part of it, not relying on other people to bring that vibe of camaraderie that you're actually going out and making sure that you're participating in that.

1:25:42 Scott Ingram: Yeah, I have so many thoughts on this. I think the most successful sales cultures that I have been a part of, it is a top-down kind of a thing. Your leaders set the tone. So the CEO's perspective on sales is really important. And one thing, this is a little bit of a cheat code. It's certainly not universal. So I don't want to make it a stereotype, but if you look at the background of your CEO, If they came from a customer-facing role in the way they grew up in their career, so they came from sales, service, marketing, anything customer-facing, it's much more likely that I think you'll find a great sales culture. A lot of times when folks come up through finance in particular, sometimes product and things like that, you get a very management by the numbers, sales is a necessary evil kind of an approach. For me, that fits in almost more to my due diligence process and the types of organizations that I'd be interested in going to sell for and the likelihood that they're going to have a great sales culture. In terms of where you are and where we are, for years I called myself and consider myself an intentional individual contributor. I carry a quota. I don't lead a team. That's an intentional choice that I have made. And yet I am a leader and I lead from the field. And we as sellers impact the culture. I think what's the cliché like, be the change that you want to see. I think at some level you just have to act out, this is what a great culture should be. But again, the greatest sales cultures, it is the entire organization understands that we're all part of the sales culture and everybody contributes. And I can already hear in the way that you're describing things like that is part of what Drata is doing because we're all supporting the deal efforts. This is not a solo thing. One thing that I'll point back to, and now I'm guiltily feeling like, oh my gosh, I've gotten out of this habit, especially on a day I was sharing with Morgan, like today was National Signing Day for me. I had 3 different deals come in. This is something that I got from Bazaarvoice. There's a daily sales tip on it if you want to go look it up. But we did these emails, company-wide emails every time we won a deal called How the Deal Was Done. And we would tell the story of this is this new client that we're bringing on. This is why they bought from us. And most importantly, these are all of the people that I need to thank who contributed and helped me get this deal across the line. My solution engineer did this. The finance team helped me do that. I had to lean on legal to work through these red lines. All product was involved. We had a call with them to talk about the roadmap, all of those different things, and being able to recognize the people who are parts of our deal. So I could go on and on and on and on, but I love that you brought up this topic.

1:28:35 Morgan Cumiskey: Yeah, I love what you said around be the change that you want to see. It's definitely, I would say, one of the things that I try to live by. And we also have like a sales channel where every single deal that comes through, we write up a win wire, we tag who was involved, and it just helps breed this culture of camaraderie and teammates. Even if they're not directly on the sales team. If you get a company or you're lucky enough or fortunate enough to find a company that everybody is kind of running in the same direction at the same speed, it can make for a really powerful buying experience and a really just fruitful place that you want to work and stay at for a long time and move up at and just really hang your hat on your sales career. And I'm very fortunate enough that I think that I found that at the company that I'm at today. It's not by sitting back and sitting on the sidelines. Sidelines and watching it all happen. I definitely have to contribute every single day to make that culture happen. I'm very, very fortunate. But yeah, I really like what you said, Scott, about doing your due diligence if you're looking for a place to sell at or a place to start your sales career at. Find the companies who have co-founders and CEOs who have been in customer-facing roles and potentially even experienced the problems that your particular product has solved for. We're very fortunate here at Drata that our co-founders started our company based on a real-life problem that they were experiencing. And it really has enabled the sales team to tell that story to our customers when we're talking about the problems that they are experiencing, because everything that we do here is just about the customer and about solving their problems. And that talk track has just been ingrained into us from day one. If you're lucky enough to find a company like that, it's really, really powerful.

1:30:10 Scott Ingram: Yeah, love that. I want to do 2 things before we wrap up. Will you quickly tell the Drata origin story, why the company is called Drata? I thought this was so cool.

1:30:18 Morgan Cumiskey: Yeah, it is such a funny story and I love telling it on calls. One of the first things that I always like to make sure that I highlight about our co-founders and our founding story is, is Adam and Troy Markowitz, our founders. They are brothers and prior to them being at Drata, they were aerospace engineers. And some prospects will pick up on this, some won't, but everything that you see in our demo environment is space-themed as much as even our demo environment in general is named Sally Ride. There's rocket ships that blast off every single time you get to a loading page, and that's very intentional, but not everyone picks up on that. We have another founder, his name is Daniel. He's our CTO. When they were trying to come up with a name for Drata, they coined D-R-A-T-A, which stands for Daniel Really Automates the Audit, which is a really funny story. I always like to tell it to prospects, especially when we're in competitive deal cycles. We have a competitor in our space that has a name that's kind of similar to ours. And it's always interesting when they ask like, hey, you guys are very similar and this and that. And I'm like, well, I bet you they don't have as cool of a name origin story as we do. And it always gets a good laugh, a good way to break the ice. So yeah, that's how they founded Drata.

1:31:26 Scott Ingram: Love that. And then to round out the culture conversation, what's your favorite thing that either you do or is kind of a company thing that you guys do that you feel just really reinforces the sales culture?

1:31:37 Morgan Cumiskey: Yeah, I really feel like we're heard. We have an AE council that takes place once a month with one of our VPs and executives where we are just free to kind of hash out things that are working, things that aren't working, things that we want to see more of, things that we want to see less of. And I think Drata has just done a really amazing job just with the growth that we've had. I think it's very, very common that you see these high-growth companies grow really quickly and things get lost in translation and culture gets lost in translation and people leave and people come on. And I think Drata has just done an outstanding job at making sure that we are heard as sellers and we all kind of have a seat at the table. As large as we've gotten in the last couple of years, I really do feel like every single person here impacts the trajectory of our business and they do a really great job at making you feel that. So when we're talking about numbers and we're talking about the success that we're having, they just do a really good job at making sure that we all know that we're doing our part. We have a seat at the table. We're all kind of in some way responsible for the direction that the company is going. And I think the leadership team has just done an outstanding job at making us feel like we matter, that we're not just numbers that they're forecasting to the business. It motivates me personally every single day to get up and do my job because I know that I'm making an impact every single day. And one day when Drata has all the success in the world, I know that the things that I did personally every single day will be part of that. And it's been really outstanding to work here and work for some of the people who just make you feel like seen and heard every single day.

1:33:01 Scott Ingram: So great. So great. All right. Let's try and tie a bow on this whole thing. I try to make this as actionable as we possibly can. So what would you challenge our listener to do over the course of the next 1 to 2 weeks to improve themselves and improve their results?

1:33:16 Morgan Cumiskey: Yeah, I think something super easy that you can do right away is schedule those one-on-ones, get one-on-one with with somebody in your company that you do not know. Maybe you've heard their name, maybe they've been in a deal of yours, but you don't know them personally. Schedule a one-on-one, maybe try to do one a week across functionally, across your different parts of your organization. Bring an agenda to that conversation of things that you want to learn about their department, how they operate, what's important to them. And yeah, that's a really simple thing that you can start doing. It will breed just more knowledge in your head about how to be a seller, how to build those better relationships cross-functionally, and only takes a few minutes out of your day. So yeah, book your one-on-ones, get to know more people at your company, build the relationships. It'll only make you a better seller.

1:34:00 Scott Ingram: Morgan, this has been absolutely amazing. Thank you for taking a very long time one-on-one with me.

1:34:06 Morgan Cumiskey: Yeah, absolutely. I'm happy to do it again whenever you want to, Scott. I mean, this has been the longest one-on-one that I've ever been a part of, but it's been super awesome and I've Really, thank you for having me on. I had so much fun.

1:34:17 Scott Ingram: 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.