Key topics in today’s conversation include:
Find J.T. on LinkedIn: https://www.linkedin.com/in/jtlevin
The SaaS(ramp) Podcast explores how tech leaders scale from product adoption to enterprise success. Learn more at www.saasrampmedia.com.
Pete Thornton 0:00
All right. Welcome back rampants. I’m your host, Podcast Pete here with another episode of The SaaS(ramp) Podcast. Exciting guest on today. I’m J.T. Levin, VP of sales at ChartHop. Welcome to show J.T.
J.T. Levin 0:19
Thanks for having me. Pete. How are you?
Pete Thornton 0:21
Doing great, man. Doing great. Thanks for participating today. We pleasure. Thanks for having me. We probably better tell everybody because you’ve got a killer background going on there. And it’s a beautiful time of year. Where are we talking at?
J.T. Levin 0:35
My backyard. I work at a little table in the backyard when the weather permits. So there’s a little key lime tree to it. It’s doing its thing. It’s almost ready for harvest. And yeah, I live in. I’m lucky to live in San Diego. And it’s just another beautiful day here.
Pete Thornton 0:50
In beautiful San Diego. No, I won’t even start with the Santiago stuff. Okay. There’s no X no way to start a podcast.
J.T. Levin 0:57
We’ll save it for the end.
Pete Thornton 1:00
Okay, well, besides my rants, like we do like to dive straight in. So you’re at ChartHop, super fast-growing company, you’ve been taking them from point A to point B over many years now. So what in this hypergrowth organization that you work in might have been the biggest challenge in say, the last six months?
J.T. Levin 1:19
Oh, the last six months. I mean, it’s always about talent, right? Any time at a hypergrowth organization. In order to scale successfully, it is 100% all about the people and the talent. And I think it’s especially important in those earlier days, because there is so much more that you don’t know, than you do know, you don’t have years of data years of history. And you don’t necessarily have a clearly defined sales process and the ability to kind of coach your reps and guide them on what to do and when and what boxes need to be checked at every point of the process. And if you can bring on folks that really know how to sell know how to manage a large strategic deal and know how to help you figure out a lot of those things, then you’ll be able to get a lot further than if you have to invest a huge amount of time and in all of that kind of coaching and training because that time just doesn’t exist. So tell. It’s always the challenge. Obviously, the market is shifting considerably in the last six months, it is very different than where it was. There is a lot of good talent out there on the market. But it’s all about the recruiting a players you can’t make that a team out of players.
Pete Thornton 2:31
Okay, yeah. Okay, I’m hearing you say two things, but you definitely keyed in on one it was kind of like talking about the talent, being able to I kind of heard recruiting and why that was important. And in the market. So maybe just a double tap on the talent portion. What is the hardest part about doing that? Is it like, is it finding the right people? Is it like getting the transition, onboarding them? Is it explaining that this is a building phase? They come from a large organization like a Salesforce or an SAP or something what is it that makes that so tough?
J.T. Levin 3:04
Yeah, it’s finding it is number one, I mean, that’s, that’s the hardest day because people that are really good at their job are now out there putting their hand up saying I’m looking for a new job, right, those are few and far between. So finding people, referrals, your customer references, that, that that kind of stuff is really big to find those folks. And then convincing them that you are not one of the vast majority of startups that are ultimately going to fail, in the coming 24 months, right, so, so selling charred pop as an organization is one of the biggest parts of the job. So definitely finding them and then, and then convincing them that this is a place where they have a career and make a lot of money and grow and chase after whatever the sort of longer-term dreams are that they have. The training piece is not as important if you get the great players on, right, if you’re bringing on a bunch of junior folks, you obviously have to invest a lot more in training. And so, there are only so many hours in the day, and you got to pick how you’re going to allocate those resources. And so that’s why the recruiting of elite sales rushes is by far the most important part of the job for me.
Pete Thornton 4:16
Totally. Yeah, it completely makes sense to me, and thanks for the clarity on that side, too. Because that’s a, you always hear about that pain point. Yeah. You’ve led teams like increasingly growing teams, especially with the hypergrowth at ChartHop was experienced, what might be like a favorite leadership moment and caveat, sorry, it doesn’t have to be from recent times like this could have been like your you won the championship with your seven year old like T ball League like I don’t know, like, what moment?
J.T. Levin 4:48
Yeah, I think at an early-stage startup, it’s all about leadership. Ultimately, what you have is a product that has potential role and some interest. But more often than not people are buying the potential of what the product is going to do than of what the product does now. And you’ve got a team of people that you have to decide whether or not you believe it. And really, that comes back to founders and Ed CEOs, and working for top leaders. There’s a lot of talk about culture, in a startup in early stage startup culture, right? What’s the culture? Like? I didn’t actually think that sort of the wrong question. I think the real question is, how does the founder behave, and is that an environment that you want to be in on a daily basis because at the end of the day, people are gold, that is, that is the culture, the founders behavior is the culture. And the founder doesn’t work very hard, people aren’t going to work very hard. If the founder has extremely high standards, people are going to hold themselves accountable to those standards. If the founder isn’t very nice to people, people aren’t going to be very nice within the team. And so really, leadership is I think less about one moment and more, you’re having somebody that you truly believe in, and that creates an environment that you want to be it on a daily basis. And that is when I think about leadership, that’s always what evaluating an early-stage startup, whether it’s for an investment purpose, or for some of the advising work that I do, or here is, do I believe in this founder or founders, to be able to take a company where it ultimately might be able to go. But I think the when you think about leadership as a behavior, it’s all about the standard, it’s all about setting the standard that number one, we do really good work, we do elite work, but also to that nobody’s too good for anything, right? A willingness to get into the weeds. If you start asking your team to do a bunch of things that you’re not willing to do, or that you haven’t demonstrated to them, or willingness, or they feel that you’re above that, you’re in trouble, you are in a load of trouble. And that is a really, really bad spot to be in. And as a leader, and as an employee in an organization as well, you’re right. We’ve all worked for folks that don’t, they ask you to do things that they’re unwilling to do themselves. And it’s not a good feeling. And those organizations that those leaders don’t tend to work out. So from a leadership perspective, I think it’s about setting that tone, it’s about setting the standard. But it’s also about demonstrating a willingness to get your hands really dirty because at an early-stage startup, if you’re not willing to do that, too good for anything, then it’s not going to work out.
Pete Thornton 7:49
That’s interesting. Okay, so I picked up three things off of that. And because it was the first piece was like, it was interesting because you brought in the concept of culture, because culture can be like the three values of but those are really artifacts of in like, there really only work out if the do as I say not, as I do just doesn’t work out. So it’s gonna be by example, you mentioned elite work. I just liked the way that rolls off. Like, “elite work.”
J.T. Levin 8:13
Yeah. Everybody, myself included, we’ve all brought a deal or turned in a project or finish a deck. And we thought, it’s a B. It’s a B test. Right? Everybody’s guilty of it at some point. The question is, is that the standard? Like, do we view? It’s okay, if occasionally you do mediocre work, and you’re aware of it, and they did give my best there could have done better. But if that is viewed as acceptable on a repeatable consistent basis, then you’ve got to be competent, the companies don’t work out. Right. So what’s the standard? But if the founder always does that is going to be acceptable. And that is not the kind of leadership to get the software company to any outcome that matters?
Pete Thornton 9:07
Especially these outcomes when we’re talking like the double and triple of headcount and the doubles and triples of revenue this crazy hypergrowth space?
J.T. Levin 9:15
Yeah, absolutely. Yeah, the famous triple, triple, triple, double, double.
Pete Thornton 9:20
That’s it. I did not hear that until too long ago. And I’m like, Oh, is that is that so like, just an aside, this is a complete aside, we just unpack that. Like I heard it. I found it tremendously helpful. I heard it like two years ago, and it was eye-opening. Like, is it really supposed to grow that fast?
J.T. Levin 9:37
I don’t know if supposed to but it is the gold standard, right to go zero to one, two, three, four, to nine, then to 18 Min. To 36. In five years. That is the that is sort of the gold standard. Although I think a lot of people like to watch it zero to one, one to three, three to 10. And then that gets you ultimately to 40 million in a few years.
Pete Thornton 10:01
Just to have those double digits in there. Yeah. But that’s even like the triple-double piece as like, oh, that’s what the that’s the whole push. That’s where the that’s where we’re headed. It gives a nice, nice hockey stick.
J.T. Levin 10:14
It sounds nice. Yeah. Makes the charts look good for sure. Do it.
Pete Thornton 10:17
Doing it’s the hard part. I know everybody else is just a historian like, look how this went on like night? Yes, it’s an autograph. What happened before this to make that work? Can we can we? Can we double-click there?
What about this question? And it’s just it like this might be retroactive retrospect. Like, either way you want to connect the dots forward or backward. But what is one thing that a sales organization has to get right? In order to grow hypothetically at that pace? Because there are so many things, so if it can only be one thing exercise?
J.T. Levin 10:51
Don’t make me pick one. I’m gonna get you two. I’m not. I’m refusing. Number one is the story. Right? Like at the very beginning, it’s a story, right? Why why do people why should people want to buy this? What needs is it going to solve? What does the world look like after they’ve done? And then there’s a bunch of sort of MIDI stories within that what is implementation look like? What is compliance look like? Right? Can you pass the SEC test, right, all of those sorts of things. But ultimately, it overarching narrative of what problems you’re going to solve, how you’re going to do it, and what the customers world is going to look after you’ve done it? Right, that that is, I think when you think about kind of the biggest challenges you got to solve, that’s number one. And number two, is you have got to be hyper-focused on your ICP, it is so easy to get distracted by inbounds from large companies or corp dev or spend time chasing deals that are just never going to come in. Yeah, start you got a core group of kind of initial early adopters, start there, figure out who looks as close to them as possible. And then let it kind of mushroom out from there. Right. But it’s just, it’s so easy. When you don’t have a clearly defined ICP, start chasing a variety of possibilities, and to convince yourself why it might work out. Right? If you work in at an early-stage startup, you spend time daydreaming about what the exit is going to look like, what the growth track is going to look like. And it’s really easy when a marquee name comes in, to say to yourself, oh, this is how we’re going to get there, right? Or we’re going to just sell to the enterprise say certain things. And being disciplined about that, because time is ultimately the most precious thing you have to be disciplined about sort of staying close and moving out. The other reason that that is so important, is that one of the biggest things you have to sell is trust. Arguably, the biggest reason that people tell you no is that they just don’t trust you. Who the heck are you? You’re 25 people. You got 15 customers. I’ve heard of three of them. Haven’t heard of the rest. You have no track record, and you’ve got funding. Like, should I trust you? Are you gonna be around in a year? What’s the roadmap look like? Are you gonna continue to be able to address my needs? Being able to say, ‘we work with company A, and you compete with/partner with a lot like company A,’ builds that trust, and that’s one of the hardest things as part of the process. Ultimately, you get to a point where you don’t have to sell trust to the same extent because the company has enough logos and clients and case studies and brand awareness and things like that, that it’s not as much part of the sales pitch, but in their early days, it is a massive piece of the story that you have to tell people, is why they ought to trust you because ultimately, they’re going to be staking pieces of their budget and political capital to pick up an early stage startup to be a key vendor for him.
Pete Thornton 14:04
Right. He has a really, really, really good point. And then just to like walk, walk me along this like razor’s edge of the ICP conversation, because like when you are curious, like Does this mean we’re moving upmarket now? Because they are coming inbound? Because that is a very tempting thing. Like how do you determine whether your ICP is moving potentially upmarket and this is the early stages of that happening? Versus this is just probably something that’s just going to be a wishful thinking or like a rabbit trail that you shouldn’t be taking and spending another 80 120 hours on between your combined team’s efforts or, or what like, what’s the balance there on like, I have this hypothesis of ICP because it’s worked so many times, but I’m trying to grow to expand that ICP.
J.T. Levin 14:49
Yeah, I think one of the easiest things to do is take a one-off and then decide that you have product market fit because one person at some company was willing to They get or maybe they’ve got a strange use case and sort of outside the norm, I think it’s about it’s fine, I always sort of think about it as kind of like rock climbing process. If you ultimately want to move upmarket, you are climbing up this wall. But there are points where you sort of have to leap and, and grab, it’s not just a sort of a steady climb. When those moments come, you still have all of the work that you’ve done beneath him to kind of prop you up to have gotten to that, to that moment. And so I think it’s about discipline. And it’s about making sure that you have multiple signals, to tell yourself that you’re, you’re ready to move upmarket, right, but you’ve still done all of that work on the wall, you still know that wall quite well. Don’t put the other customers in the rearview mirror just because you’ve taken that leap up to sort of that next rung up, you still should be able to make more money in there, eventually, maybe a time will come where you’ve you’ve said, okay, now we’re only going to sort of service this market over 200 employees, or whatever kind of your metric is for, for dividing that what it just the I think the biggest kind of trap that people get caught into, is having one customer and deciding that, that you’re taking the good signal and ignoring the bad signal that oh, there’s a, they’ve got this unique structure, or they’ve got this new product launch, it’s a little different than all of the other stuff that they’ve done. We’re really there for the outlier use case at this company. And not because all of the other companies that look like them also have this need.
Pete Thornton 16:44
Right, right. I mean, particular, something you designed for that, like one of my early SaaS companies I was at, and we got a whale early, really early. And we decided that was nice and feet, and we got like two more, as well. And it was just enough to throw us entirely off track for years and are not so amazing product, in fact, but just and then we started tailoring everything we did to their whim. And we were just led by the nose, essentially by this one account. And it was to the detriment of all the other accounts. And yeah, the city piece.
J.T. Levin 17:18
It’s a common story, take care of the books that brought you to the dance. while also looking for a few new dance partners. Blending those two things together is really how you ultimately find some of the most successful endeavors and sales teams.
Pete Thornton 17:37
Yeah, that makes sense. Okay, yes, thanks for the two answers. By the way, I rarely get one. I rarely get one.
J.T. Levin 17:43
I’ll give you more if you’ll give me time for it. But yeah, it’s pretty difficult to narrow down to a single one.
Pete Thornton 17:50
Yeah, I know the challenge. Okay, so you’ve done this for awhile, you’ve been in the game long enough to have some wisdom built up. So what would you give yourself as a tip 10 years ago the J.T. of 10 years ago?
J.T. Levin 18:09
I think there’s Number one, he looked for three things. I think a lot of people focus too much. If you go to work in early-stage startups, three things you ought to focus on. Everything else is secondary window dressing. Its team, its product, and its addressable market. That’s it. There are a lot of people say, oh, I want to be a sales manager. Why? Because it feels like the logical extension after account executive, do you know what’s involved in being a sales manager? Now? No, not really. Does your manager seem happy? No, not really, oh, I want to be a VP of sales or I want to stay in an account executive. Right? If you get the team, the product and the addressable market, right, everything else works out. Right? Snowflake one of the biggest IPOs of all time, right? guarantee you a Senior Account Executives are complaining, right? About the ride that they went on, they’re not sitting over here gone. Oh, wish I was VP of sales. Say Tom, there’s a lot of VP of Sales very, very mediocre companies who’ve spent the last two, three, four years in a very tough job struggling along, maybe haven’t made as much money and there are opportunity costs to that job. And that’s because the team, the product and or the addressable market were not correct. So just look for those things. Everything else will work out. That’s the biggest thing in an early-stage startup. He starts and I think it really is he in that order. It’s all about the people in the team. And then from there, are they a customer-centric? Like, are they obsessed with the customers? Are they obsessed with building a product that delivers value? And are they doing it in a market that has large-scale opportunity duties. Yeah, that’s it focusing on the role you’re going to add or get a $5,000 raise here or there. It’s all inconsequential because if you had hitched your wagon to the right cart, everything worked out.
Pete Thornton 20:16
Okay, okay. Yeah, there’s a famous like Warren Buffett quote that goes something similar. Don’t worry so much about like the I’m gonna hack it and this was like the moat you’re in but like the time you’re attached to or something like that.
J.T. Levin 20:28
Yeah, of course, there’s one of my favorite books Good to Great, has a variety of lessons in there one of them being to make sure you get the right people on the bus. When you find somebody who’s great. Just get them on, you’ll figure out where to slot them. I think about it very much as the reverse challenge. I’m looking for a great bus. I want to be on a great bus. If I do that. Everything else will work out.
Pete Thornton 20:57
Yeah, I have a colleague who he is. Postman, our organization was his fifth outstanding hypergrowth startup. And he just does very well with some of the some of that equity. He’s just hanging on to he was just like first 30, at HubSpot and things like that yours. Yeah. And he’s a picker, he’s a very he’s a stock picker is like, he just knows how to choose them. And then his roles within kind of vary.
J.T. Levin 21:19
That’s exactly what it is, especially for on the sales side of things where so much of your compensation is tied to commission. And VCs get all the credit, right? But the business model is pick three or four out of 10 that are winners. Early Stage software sales folks have to pick one, you make a big compensation bet a single horse and an elbow works out but picking the right company is the whole thing. Because it doesn’t matter how good you are. If the product the team and the addressable market are right, you’re not gonna make any money. Yeah, yeah, at the same time. On the flip side, there are a lot of very mediocre folks at zoom at DocuSign who I’m sure had themselves have really nice last couple of years. They pick the right company Right Place Right Time. And on there’s some luck involved and to deny it is wrong approach because there is a there’s a lot of luck involved. And you got to be cognizant and appreciative of that.
Pete Thornton 22:20
I’ve got a buddy who did very well and one of those and he’s got a place nearby you with a view of the ocean. So I’m like, okay, yeah, send them this piece of the podcast be like, what’s the shoot? What are we talking about?
J.T. Levin 22:32
Yeah, and look: nothing against those folks. Just appreciate if the role that luck plays because nobody got where they are, just doing it on their own?
Pete Thornton 22:41
Yeah, totally. Alright, so what about? What about, like, challenges associated for growth? Actually, why don’t we just combine one? Will you tell us a little bit about like your journey to ChartHop? Like just what was the like, because your VP sales, and then char Hobbs, a really, really solid hydro SaaS company. So like, how did you get there personally and professionally? And then what is it that made them take off? And then we can kind of start unpacking some of the challenges around some of that growth? But yeah, maybe start with you like, what about you? How did you get there,
J.T. Levin 23:13
I have always been in very early-stage companies, I’ve never joined one that had more than 5 million in revenue. Even my first company yaks, which is now a publicly traded very good company was under that what in my class of sales reps took us from, I think, 12 to 20 employees. I just like figuring things out. I like the work of figuring things out. And more importantly, I like the people that sign up to do it at this stage in the process, which is something he can’t discount. These are my kind of folks, the people that accept the challenge of figuring out a bunch of things that nobody has a good answer to, are just the kind of people that I want to be surrounded by all day, you spend too much time at work, to not be happy, surrounded by your co-workers. And at least for me, maybe there are people out there that can do it. But I’m not one of them. I have to sort of genuinely liked the team and the mission. And look, I’ve met some of the great, great friendships and relationships, I met my wife at work in that process. And so that’s why I’ve always been attracted to this. This is my fifth early-stage startup. And I’d worked for the founder once before. One of the biggest things in evaluating any job is one of the toughest parts to evaluate. We keep coming back to teen here and leadership and founders is the founder, right? You spend a couple hours with a person in an interview. But to really know, how are they going to react when things aren’t going? Well, because it’s only a matter of time, right? We’re going to hit a point where things are not going well. We’re going to lose a big customer. We’re going to have an outage, like we’re going to have a problem at some point. How are they going to react? Are they going to pull themselves? Right when that big Series C comes around, right? Are they going to, they’re going to take some off the table and think they’ve made? Right? Like, how are they going to react? And so, that’s one of the biggest risks you take in signing up for an early-stage startup, I had worked for Ian, who’s the founder once before, at his last company, a place called sailthru. That would very well, and, and we’d stayed friends. And so the chance to work for somebody and you trust that is product-centric. And then you can evaluate the addressable market yourself and check fell out of the box straightaway. So I was third employee, there were just a few of us sitting in a glorified the kind of closet that only we work could make sound appealing credit to their marketing team there. And, and then it’s been we’ve kicked on from there are a little over 200 employees at this point. And, yeah, it to your point, we’ve, we’ve sort of checked all of the boxes, in terms of kind of growth and Arr, and those sorts of things. So, for me, it was about being able to work with somebody that I know and trust and truly believe and to get to here. And I guess there was that, that that feeling was mutual. We actually were out for brunch and I said, I think are you looking for a new job, and he said, I think I’m gonna raise a $5 million seed round from Andreessen and our eyes kind of locked and that was it. You just knew right in that moment that we were gonna go do it. And here we are.
Pete Thornton 26:28
And that’s cool. That’s a fun little story right there, too. I can just like see the moment happening. Yeah. And the fact that your fifth, your fifth like, there is something that happened there are a few cases, there are a few cases there are two folks in this maybe like 200-ish interview cycle that this path I’ve been blazing and, and they have come from SAP and been like, Wolf, I’m ready for something different after about a decade. And they went and they’re like, they’re like seed series A CEOs, very product heavy CEOs. Because they’ve seen it there. And they’re like, they wanted to see if that how far they could build it from scratch. And it was just like this flip. And then and then otherwise, most people have been very—it maybe it was coincidental, the first one, but after that they’re just running this cycle.
J.T. Levin 27:17
Yeah, it’s a sickness. Yeah, I yeah, you just, I remember I interviewed at a very large company. This was maybe five or six years ago, couple before it took a couple of rolls, rolls back company with a few 1000 employees. And it was a senior account executive job. Are you gonna make a bunch of money and all of that, I remember what I got off the elevator, I walked in the door closed. And I just sort of looked out and just thought, well, this is an odd for me, right? And then you go into the interview. The sales process sounds very robotic, and everything’s figured out, everything’s well-defined. And you have to do these things. And here’s the sort of the support team and it’s but it doesn’t sound like it has much creativity involved. And interestingly credited to that to that VP of sales, he figured it out at the end of the interview kind of went, I just don’t get the sense here that into this. And he was right, I was not into it at all. At that point, you can’t cancel the interview, you’re standing in the office, but I had already sort of decided in my head that I didn’t think this was for me. So yeah, I’m just kind of a junkie for this thing. I really like it. I like the advising work, as well help people sort of figure out this stuff because it is, it’s a completely different challenge than then trying to go from 25 to 100 million in revenue, the skill set, the problems are all very different. And I just like these problems.
Pete Thornton 28:41
Yeah. Okay. I understand this. Just, it’s interesting to hilarious with that one. What are the problems then? Like, what are those problems? Because they’ve got it figured out there? They have resources at their disposal. But so what are maybe if we can limit it to a few Yeah. Problems of not only like being small, but moving fast as well.
J.T. Levin 29:04
Yeah, everything’s a problem. You start with nothing, that everything’s a problem where everything’s an opportunity. The biggest problem, the first problem is nobody knows who you are. That’s the biggest initial sort of day-one challenge and you have some semblance of a product that the further along it is, the better, but nobody really has a clue who you are. So you got to get out there. But you also have to get out there in a way that’s going to generate some sales, which means you have to balance creating a bit of brand awareness with really the in-the-trenches, sort of head-to-hand combat of making an actual sale. So in a lot of cases, you’re doing bulk. You don’t have the marketing cover of making sale of people getting some brand awareness and then you being able to sort of go and talk to them about you have to do both pieces of that when I started to ChartHop or website consisted of a Google form that said something cheesy as hell like see the future of HR, then you could just put your information in, and I would get an email when somebody filled that out. Right? Not a lot of people filled that out. So that’s number one. Number two, building and generating trust, right, making sure that people are confident that you’re actually going to deliver, and that they’re excited about what you’re going to deliver, they’re willing to get vested in what you’re going to deliver, is the next part, figuring out the story, who wants to buy it? And why? Or what problems do we solve? And who has those problems? We think about it the other way. And that there’s a bunch of questions that people ask that, that fall on the salesperson to convey answers to, but ultimately fall on other people, it’s probably deliver at the organization. Right? Great, we’re gonna sign a contract, then what happens? And ultimately, they’re sort of testing you to see if you’ve got your stuff together, right? Well, we’re going to implement, we’re going to do this, there’s going to be these kickoff calls, this is the process. Do you have that stuff under control? Right? And can you articulate it in a way that’s going to really create competence from the buyers? Like, those are the biggest challenges right out of the gate, but I mean, I spent a good like three hours working on a decK. I bet they’re probably three weeks. And we needed a little bit of adapted to kind of tell our story. And I turned to the rest of the company, all three of them, and say, I’m really looking forward to the day that we look back on this deck and just think, Wow, that was silly, because I knew, I knew that after two or three weeks, there was no way that what I put together was ultimately going to be the thing and I figured I would get maybe two, three months out of this deck. I got one call out of it. And just thought, boy, that thing is crap. That did not resonate. So that made the sale anyway, but that decK was awful. And it didn’t hit on the problems. It didn’t do it in a cohesive flow. Right, it was just way too sort of Scattershot and learning that and doing it in a way that you have to do it quickly. But that ultimately you don’t pay too big a price for the mistakes mitigating the mistakes is another kind of key problem.
Pete Thornton 32:24
Yep, okay. Okay. Yeah, I’m hearing like obscurity, like trusts getting the story. All the things that you’re the problems of building?
J.T. Levin 32:32
Yeah, no, I learned this lesson about obscurity and trust, in a most painful fashion. I was working at state Altru, we were probably about 40 people at the time, a bit. Arr was somewhere in the kind of the $6 million range. And I thought I had won the deal. With one of the largest, most complicated, we were an email service provider, largest, most complicated kind of email sending organizations on the planet, one of the sports leagues, which has all kinds of complexity, massive user base. And ultimately, I think I’ve won this deal. And a guy calls and says, Listen, J.T, I think you’ve got the best technology. But if I buy you, I’m getting fired, and it doesn’t work out, I’m getting fired. And I’ve got a pregnant wife, and I’ve got a fresh mortgage, and I just can’t take that risk. So I’m buying this other company instead. And it’s a fatal objection, you can’t handle it. No, Don Wesson, I think it’ll like, it’ll be fine. Just trust me in a workout. You just don’t have the track record for that. That’s another consideration as you’re moving upmarket is that you do deal with companies that have less appetite for risk that have more kind of political considerations internally. And that was a really difficult lesson in trust because in my mind, I’d already cashed that commission check. And it was sizable on a seven-figure deal. So the hard lesson in trucks and then you learn that you have to incorporate that be proactive about that. Because no matter how excited your buyer or champion gets, there’s a high likelihood that when they walk into the CFO or the CMO, or whoever it is that is ultimately your economic buyer, office. credibility and risk are going to be one of the first questions they asked about better informed than with a really good story.
Pete Thornton 34:22
Yeah, yeah. Yeah, that’s important. Great. Okay. Okay, then, then. Maybe like, what would be the hypothetical vision like, what would be the next steps from where you’re at today? Just if you were thinking it through, like, it was almost like January one or something like that, like, like, what would be the places it would go from here?
J.T. Levin 34:46
ChartHop? Where ChartHop will go from here?
Pete Thornton 34:49
Yeah, like, what would that vision look like?
J.T. Levin 34:53
How to get there is the challenge, right? At this point, if you’ve, we’ve hit a point where it becomes about process and scale and starting to expand. So, you talk about ICP from sort of that kind of mushrooming effect, you have to start to now expand outward, right? Broaden, broaden the scope, a lot of that is in partnership with product, who is for me product engineering most important functions in a real estate startup. They’re the biggest determinants of success and failure. But it is really professionalizing a Salesforce now starting to understand how to kind of train, develop, scale promote from within, right, those sorts of challenges. It’s much more of a team, sort of selling process now than that it is about sort of just plugging in great talent and doing everything we can to enable them. Yeah, that part’s really important, but you have to do it in a much more methodical fashion at our current size and scale.
Pete Thornton 35:53
Okay, okay. Yeah, makes sense. And that’s when you get the cornerstone and now maybe trying to start stacking out those brick after brick.
J.T. Levin 36:01
Exactly right. Yep.
Pete Thornton 36:04
Well, killer journey. You mentioned founder already he might be in part of this group. But if you had two or three people to kind of like offer some gratitude towards for any piece of this like wild like SaaS(ramp) of your own your personal like building block from one of these five companies? Anybody come to mind?
J.T. Levin 36:24
Wow. Yeah, I mean, he and certainly gets a lot of credit of. I’ve worked for him almost seven years now across two different companies. And it’s been great, how we’re learning Yext, which is where it started, for me, one of the brightest, most driven minds I’ve ever had the privilege of, of surrounding myself with that, that is another man that I hold it in the highest regard. And I think number three, I’ll make a group to so much of the amazing engineering and product talent that I’ve been lucky enough to sell products for, over the years, you can’t sell things that don’t exist. You can’t sell crappy things, either. Team product and addressable market. And if it weren’t for the fact that I’ve been able to work without standing engineers of CNE, CTOs, VPs of engineering, then the journey would look a lot, a lot rougher. A lot of sales reps are judged, they had a really short skid, they were only at that company for 13 months, or they were only there 18 months, why? Well, because the product stunk, right, the product stunk, and they couldn’t, they couldn’t make it go. And I’ve been really, really lucky and blessed to be able to sell a lot of great products and, and credit to all of the engineers and product folks that have built those and enabled that so much of this journey to happen.
Pete Thornton 37:53
Yeah, well said. That is totally true. Completely true. Yeah, that’s a great one. That’s a good one to wrap on. I really, really liked that. And, yeah, we’ll plug that in. And Live Live from San Diego today. That was a really well-put session. I know the audience will appreciate those insights.
J.T. Levin 38:10
I hope so. Hopefully it helps. Find me on LinkedIn, if there’s any more I can help. Like I said, I’m kind of a sicko for this just getting into it figured out how to help you be more successful. So I can do that for any of the listeners. Please don’t. Don’t hesitate to come find me. But thanks for having me. It’s been fun.
Pete Thornton 38:33
Brilliant. Thanks, man.