#48, Vishal Sunak, Founder and CEO of LinkSquares — Decision-making frameworks, the most potent management technique, how to build a fierce network from scratch

Welcome to From Startup to Grown up, the podcast. My name is Alyssa Cohn. I'm an executive coach, an angel investor, and the author of From Startup to Grownup. Each week I talk to founders, creators, advisors, investors and builders of all kinds about their insights and experiences in going from startup to grownup. Welcome back to From Startup to Grown up and today my episode is coming to you from Collision, the tech conference in Toronto. I spoke there in June and I interviewed Vishal Sunak, the founder and CEO of Link Squares, a web app for legal and finance teams to automate the search and reporting process around company contracts. Now, you may not think this is a sexy business, but a SaaS business that goes from 1 million to 10 million annual recurring revenue in two years does not lie. Vischel and I had a great chat talking about how we did that and also covering topics like mentorship and how important that is for all founders and I would say all professionals really. And actually how important shadowing is the idea of someone being in the room when decisions are made to see how it all works, even if they don't have a role in it, and how much he got out of that in his prior companies. Vishal also shares his frameworks for decision making, the specific steps he used to learn about this business and about the legal ecosystem, which he knew nothing about at the beginning, and how he built an incredible network to help him succeed. Vishal is a really impressive founder and professional who's thought deeply about the way he leads and you're going to get so much out of this discussion. So please enjoy my great conversation with Vishal Sunak, founder and CEO of Link Squares.

Vishal, welcome to the show. I'm so excited to have you tell us about Link Squares. What is the founding insight about Link Squares?

Well, it's software for legal teams, in house legal teams and we saw a big business problem to solve. I was working at a tech company that got bought by a bigger tech company and the bigger tech company asked us what was in all the contracts we had signed with our customers. Like very specific questions, couldn't answer them. And then my co founder and I, who worked at the same spot, we said this is really interesting, like why is this so hard? Like we're nothing special, we're just like a regular run of the mill B2B software company growing fast. And that was a moment of genesis to go and figure out if other people didn't know what was in contracts they had already signed but had no way of ever understanding them in whole, what they agreed to and then we built this company.

Yeah, it's like a really unsexy business. Right? Contracts, I think are unsexy. But you said, oh, we're going to find out what's in these contracts and make it sexy.

I think contracts are sexy.

They do, yeah.

They're the lifeblood of the business. Right. You're in a contract with everyone, your employees, your suppliers, your vendors, your customers. Everything is a contract. Even to throw a great conference like Collision, you're in a contract of some sort.

Yeah, I guess that's a good point. By the way, we're at Collision. I should have said that in Toronto, doing this live. Why did you decide to come to Collision, by the way?

Yeah, it's really important to me to give back to the startup community and help people on their journey. A lot of people help me too. And so much of it is wrapped up in the day to day of running this giant company that we have now and managing our investors and all that. But making opportunity in my year to tell people the journey and teach them. A lot of people taught me. I asked hundreds of strangers to help me. Like, with no context for who I am, I just like, will you help me? And so many people did. And I kind of feel the responsibility to kind of rebalance that and give back.

I love that. I think that's amazing. And I was going to ask you anyway about mentorship, so maybe it's a good time to talk about that because I know that you something that you're really committed to is mentoring others and your advice you have for other CEOs is to get mentors. Can you talk about maybe the early days of your journey and how mentorship or even just advice and counsel helped you? Yeah.

Mentorship for me has never been something that was truly like formal in some way. I was never offered. Like, you're going to be in a mentor's program and you're going to get assigned a mentor and you're going to be its mentee and you're going to ask them questions. But it was kind of more like organic in the sense that I have worked with so many subject matter experts across so many different disciplines. Product engineering, legal, finance, marketing, go to market strategies of an executive level running the business. That when you're orbiting around someone who's a real expert, and you usually figure it out by title, VPC level, board member, investor, you're orbiting around someone who's like a real expert in something, the more time you spend orbiting around them, you're going to gain knowledge which is like third hand. Just by watching them make decisions every day, you're going to then get that much closer to being able to say, I've seen this problem before, we had a solution or a way of thinking about it. And I've collected these people in every arc of my career. Even before I was in technology and in my first job out of college was in the defense industry, just finding people who just knew a lot. Like 20 years of doing this and you hang out with them enough, it rubs off. And we love that. I call it the expert apprentice model. And we built the company that way. We built Lin Scores that way. In the early days of like, my job was to hire the greatest executive team that could then recruit people who want to become just like them. And that model is so powerful. And I've seen it in my own career and we've seen it in Lin squares too. It's just like a beautiful thing.

And it's a beautiful thing. I love the idea of apprenticeship and just sort of sitting next to someone and being in the room and listening to how they approach problems. But when you say that you hired the best people. So take us back to the early days of link squares. Honestly, early stage startups can't hire the best people. Like no one's ever heard of them. They can't pay them any money. They have to hire believers in a way. How did you think about hiring those first people? And how have you thought about kind of, let's say, as you've grown, earning the right to hire different kinds of executives?

Boot camps and an educational, kind of certificate type of programs attract individuals that have high intellectual curiosity and also a lot of grit and determination. One of those boot camps was called Boston Startup School. It rebranded to Startup Institute. When I wanted to make a career change, I left my job in the defense industry. I did this thing which was called Boston Startup School. And it was free. It was seven weeks of your time from there.

Wait, and just to clarify, it taught people how to be in a startup. Like, what did you do?

Functional discipline. So like, you could learn about web apps, you can learn about UX and products, you can learn about marketing, you can learn about sales. And so if you wanted to change your career, you could spend seven weeks just learning the lingo and making connections to kind of make that leap. And that's how I got into working at backupify, which was the place that got acquired, that it came up with the idea. And so our early hires were all graduates of this program, Startup Institute. And what was really Cool is like some of them were former founders. They had given in a rip and it didn't go great. But like they had that kind of founder determination and founder grit and perseverance. People that were highly intellectually curious but never complained. And my first employee is still with me. My third employee is still with me. My fourth employee is still with me. My second employee just moved to California and so that's what he wanted to do. But those folks that we hired in the early days, they're still here six years later, seven years later, like and it's still that intellectual curiosity that keeps them here and that grit and determination, now that they've seen it, basically, basically get grown from nothing. My first executive hire was cto. I was running product and engineering casually. I have some background in IT and I, and I had to go raise capital. Like I decided I wanted to go raise capital, do like an angel round. I couldn't run it so I hired two guys, Andrew and Eric. I hired Andrew to be product manager and he had been a founder of like an e commerce company. He had that grit and determination. I taught him everything I knew about software development and managing it from high level. Eric I had worked with previously at backupify. Eric's the best engineer I had ever worked with. I didn't do a big executive search. I said to myself, well, Eric just knows everything about everything. Front end, back end, DevOps, AWS coding, best practices tests. Like I don't think he'll ever have a boss that's not like, you know me as a CEO. I said like, come on guys, let's go do this. And that triad we call ourselves internally is a joke. The triad of the three of us had just been together building and innovative products for a long time. And Andrew grew up in the business. Eric was already an executive, kind of like Andrew grew up in the business too. And it was just about people who could see the opportunity ahead and weren't afraid of hard work. And in the early days we put in a 12 hour day every day we'd leave. It was in office back then this was like 17, 18, 19. We were just going to our office, cranking out a 12 hour day, coming home, couple hours off, back on the laptop at nine, work till midnight, do that for three or four years and that is still the same drive we have. Even the company is much bigger.

How big is the company now?

It's about 420 employees. Started with zero, just started with Chris.

And I. I know. So wait, is Chris part of that triad? Will you Talk about the triad.

It's the engineering, product, innovation triad. So unfortunately, there's only room for three of us, and that's a triad. Me and like, my quote unquote, Chief Product Officer Andrew, and my cto Eric.

Okay, so what does Chris do?

Oh, no, Chris has been a huge part of the business. He basically run every department in the. In the business over time. I was the engineering side and the product side. In the early days, Chris was like the sales and customer success. And we kind of co shared a little bit of doing a little bit of marketing, and we had a great union as co founders. Just kind of split the work down the middle. You take that stuff, I'll take this stuff and then sync up when we need to.

Got it. So you were an engineer and now and you, I guess, decided, or you and Chris decided together that you'd be the CEO. How did that go? Like, how did you as an engineer, learn to be the CEO? That's a very different mindset.

A lot of misconceptions of what CEO is, right? Is it wearing a suit and going on podcasts or whatever? And it's definitely not.

Just to clarify, Vishal is not wearing a suit, but he is.

I'm in a T shirt. Being CEO is, yes, being like the figurehead of the company, but it's getting the strategy right about what we do next. I often say that, like, my. My job as a CEO is to worry about the future and think about the future, and there's really no one else I task with that other than myself. It makes a lot of sense that we wanted to become an AI company. So much of our journey is technical. It's like, can we build an AI pipeline that can process these contracts and read them? And can we invent the technology behind the scenes to be able to do it? And. And like now, I often tell people, running Link Squares is not running one company. It's actually running four companies at the same time. It's a company full of people and a best place to work and great benefits and fair pay and career laddering and performance reviews and dealing with all the issues that humans have. And do people want to work here? Do they want to tell their friends about it? All that goodness in the people, which is like a lot of the whole thing. And then the company is also like financial metrics and Unit Economics and SaaS. Unit Economics and burn rate and P and L and income statements. And you need to kind of learn that along the way. I mean, I hadn't even taken a basic accounting course in college. So I had to just learn it, like, practically with experts being like, okay, look at this and look at that, and this is this, and you can learn that. And there's enough published stuff on the Internet. The third is like, Lin Scores is an asset. It's asset. We're owners in the company. I'm owner of the company, and investors are owners of the company, and employees are owners of the company. So then we have to make decisions of how to run the company, what's best for the asset, the enterprise value of the asset. And then the fourth is like, we're running a company that's a brand, and people make brand decisions. Where you live, what shoes you wear, what watch you buy, what car you drive, Everything is a brand decision. Same with people looking for a job. Like, do I want to work here? Does this seem like a good place to work customers? Do I want to buy this software? Do I trust them, that they're not going to waste our money? So I actually have to run four of those at the same time. And then the tricky thing is that when there's ever a conflict between one or the other three, it's like a big decision. Sometimes all four light up into, like, every. Like, a decision we make is positive, like raising. We raised $100 million last year. Obviously, all four of those things go into, like, it's positive. But then, you know, you look at businesses that are doing layoffs and reductions, and, you know, they're. They're saving their unit economics and they're trying to save their asset, but it's hurting the people in the brand. So it's like a little framework, like I have, like, which one of these four is this decision going to hurt? And if it's more than one, it's like the biggest decision you've ever made in the company.

So what's an example of that? Where they were in conflict and how did you think it through?

Yeah, like, well, I mean, just generally with the macro economy being what it is, like, we have to protect the asset and we have to run the company on unit economics. And then it's really the trade off between, like, if we decide not to further invest in our operating structure and expenses, will it hurt the people who work here? Like, if we can't match insurance premiums at the percentage that we're matching every month, and we said, okay, well, we're going to reduce it by 12%. Like, that's going to have a huge impact on the whole workforce. But it's best for the unit economics. But it's in conflict with the people. And then as kind of decisions you make impact your brand and you get a reputation like, oh, that that place is just like a boiler room. Or like they don't care about anyone. Like, they don't do anything for us like, because, you know, people are trying to manage the finances in, in a, you know, hard economy right now, and the macro being what it is. So that's like the framework that I think about decision making now. I've thought about it that way for a long time.

Right. But I guess I would love, if you have it, an example of how like sort of a decision, an actual decision that you made that where you had to kind of take into account that framework and then where you landed on that decision and how you thought about it. This one come to mind?

Yeah, sure. We had raised $100 million and we had plans to like, you know, grow 100% year over year, which is what we do every year for the last four years. And, you know, starting to now think about, like, well, maybe we should cool off a little on the year over year because it's going to hurt the value of our asset. To be a company that doesn't look, quote, unquote, efficient at large scale, but then not investing in, you know, different expenses to make the company better, you know, puts strain and pressure on different parts of the business that are just expanding because we have more customers than we ever have before. Like, some months we add like 70, 80 new customers. Like, that's a lot. And there are certain parts of the business, like customer success or implementation, where the volume of the scale of customer acquisition is actually choking and suffocating the ability for us to work. And, you know, making a hard decision that's like, well, we can continue to not, you know, stand up a new department, but how long can it last? And then if that leads to, like, higher cancellations because people are not getting the value they need out of it, or they need us to go just an extra inch or two inches further for them because they can't do it because they're resource constrained, then like, that's what we've been dealing with, like, pretty much for the last nine months is, is just a balance between, like, when are we going to burn out the employees so hard because we're trying to tight manage the budget so tightly. And then it's like, well, we got to stop this now because, like, the people are what do the work in the company. And we can't forget that when they're like, Full crank every day. And they're like, well, I just can't even keep up. And stuff starts falling back. We actually need a team that's twice as big or three times as big to do this one thing, whatever it is, implementation, support services, whatever. Then it's like saying to yourself, well, I'm now making a trade off between the humans that work for us that we care about so much, and also what our P and L looks like. And you know, in most cases it's like, all right, yeah, how much do we need? What's the proposal to increase the budget? And. And you kind of have to calculate ROI like that.

Yeah. It is so complex. Like, I think people don't really understand the levers in running a business and especially in dealing with those people. Those people. How did you as a leader learn to manage? Like what, what are the moments in time that you can think about that helped you learn how to manage?

Being CEO is a little different than, you know, I don't know, being a manager of, you know, individual contributors. The thing that I learned about executive level management is I only really tell the executive team what is important, what the goals are, what we're trying to do for whatever reason, what we're trying to do to make the company look as sexy as it possibly can from a unit economic perspective, because we're going to go do a capital raise in a year and then I only prescribe the what at a high level and I'm not really in charge of the how. And that, that's my style and how I run my executive team. Shame on me. I'm trying to tell my cmo, who is an expert, she is an expert in all aspects of marketing. Shame on me if I'm trying to tell her how to run our demand gen function, you know, but it's like, wherein we're in constant collaboration and communication. I end up, you know, being a cheerleader, being a therapist when things aren't going well or breaking conflicts that, that, you know, mostly are impossible decisions that no one knows the answer to.

Is there an example of a conflict that you brought, like a tie that you had to break? Because that's a very important role as a CEO.

Yeah, sure. It's, it's like, well, we've assigned whatever budget that we have this year to say engineering and we require, let's say 10 or 20, what we call enterprise features that appeal to the implementations of larger companies, like user permissions and audit logging and various security type stuff that can be embedded in the app. And we're now in conflict because our sales team that's dedicated to hunting bigger deals, we have a dedicated big deal team. Enterprise team need the features to win much larger accounts, but we don't have the resources inside of engineering without increasing the budget. So then it's that ROI calculation of the longer we wait not increasing the budget of the engineering department, the longer the enterprise team is going to not be as effective at closing six figure deals. So if we don't do anything, we are not going to get these big deals. But if we do something which is increase the budget, build the features that the enterprise team needs, then good things can happen and we can probably for whatever we spend yearly, let's say we spend a million bucks on a team of six or seven people or whatever, we could generate that into tens of millions of dollars of wins. Then like that's like a conflict that you know, I broke recently which is like just do it. Yeah, just do it. Like, I don't know, like just do it.

Like what made you say just do it? That was just your gut or I'm.

An, I'm an engineer. I mean it's like everyone's obsessed with growing their ARR. It's ARR. I grew this, I do that. You know, we're at this stage, we're trying to do this this year and ARR is a lagging indicator of how great your software is and how awesome your brand and marketing engine is. It is the reflection of those two things. You don't hire a new sales rep and get ARR. That's not how it works. You hire a new sales rep which has the ability to work leads turn into opportunity and pipeline to then become a customer. But it's really dependent on the fact that the software meets the buyer's needs and the marketing is tuned in such a way that the buyer believes they're buying the best system in the market. And in. Too many people are obsessed with ARR modeling. But there's two inputs that go into that and if you're short on either one of those two, you're not going to get the results you want. And this is that exact problem. Like the software is deficient for the needs of a customer that wants to give us half a million dollars a year and we would win that half a million dollar deal if we had three more features, five more features, 10 more features that appeal to them. So that's how you break it. That's how I think about it.

Yeah, you sort of think it through in that way.

I only get the hardest problems. Now, Alyssa, like all, we've hired so many experts that they take, they take care of the easy and the medium problems. I only get the giant, hairy, ugliest problems that have the most uncertainty. And if you get it wrong, there's massive consequences. I'm the only person who can make decisions like that.

Yes, true.

It's, that's a hard job. That's, that's the job of being CEO.

I love that.

That's what it becomes. Really.

It's, it's so true. And I love the way you say that. And also you say with a lot of confidence, do you ever experience like self doubt imposter syndrome as you're, as you're dealing with these difficult problems and also which direction to go and whatever.

It's certainly hard when you don't know what the right answer is. But we can measure it and analyze it enough times. Predicted, forecasted, if we can run models, run simulations, create more like rollback plans. Like, okay, if we go do this thing and it doesn't work and we're tracking metrics and these metrics are not improving, then we know what to do next to then use whatever is not working as an input and to keep iterating on it. Try to take an iterative approach. There are no real situations where it's like yes or no. Like if you decide wrong like that the journey is ended. Like, I don't like to do that. And there's, I've never really been asked to do that, but it's more like these decisions on strategy. You know, at the end of the day, it's hard to, it's hard to be an imposter on something that no one really else can tell you what the answer is. You wake up one day and it's like, how many people are subject matter experts in ling squares? Like, okay, well they all work for us. They all work for me. There are people I've worked with for five or six years now, and essentially we're just by ourselves. I, I can't go to another CEO and be like, solve this business problem for me. There's 100 hours of context that they would have to have and historical context, all the decisions we made. And so you kind of got to be confident enough to be like, there is no one else left in the world who can make this decision. It's me and a handful of others. And let's measure it and do it and if it doesn't work, we'll just fix it. It's like keeping a level Head and a fixer attitude. Even when things are going great, just like, keep an eye on it, make sure it continues to go great. It can move on to the next thing.

I love the way you think about that. That's great. So to your point, you're an expert on link squares. Absolutely. And I think now you're an expert on your customer market. But it wasn't always that way. When you started the company, you'd never met a lawyer, court chief legal officer.

I had no context for the general counsel. I had no idea who they were. The companies that had worked at didn't even have a general counsel. So, so much of the early journey and all the people I mentor and, you know, people who are going to listen to this podcast, it's like, get obsessed with the buyer Persona. Don't get obsessed with the solution. Very rarely is it a piece of software is going to change your life more. Is like, you understand me so well and you understand who I am. Like the general counsel, who are they? Well, they mostly study, like English, history, philosophy. They, they like reading. I'm an engineer, so, like, I don't even really enjoy reading. Like, I like excel in math and I'm just different from them. So you gotta understand them and you gotta understand, like, what their motivations are, what their job role is. Like, where are they in the executive team? Are they the inner circle on the power line with the CEO? Are they on the outskirts? Are they viewed as a cost center? Are they viewed as a business enabler? What. What were they in the past? What do they want to become in the future as baby boomers are retiring? How does that make a wave to like a new, modern general counsel who wears all birds and use an iPhone? And how are they thinking about technology? You have to understand all of this stuff to build software effectively.

Yeah.

You can't rush it. And in the early days of founding a company, it's like, don't rush to build software.

Yeah.

It's not problem software. So software solution and then customer last. It's like, problem, Put the customer next to it. Validated. Do you have this business problem? Are you feeling this pain? Like, tell me about it. How do you. How would you solve this business problem inside your company if I wasn't talking to you? How do you do it today? Then you can form this, the foundation for like, what the solution can be, but like, if you do it the other way, it'll never work.

Yeah.

Even if you're a subject matter expert, then you're putting too much bias into Your view of the world. And there's definitely, you know, different ways to make a cake. Figuratively.

Yeah, I love that. And I love that conceptually, but like, walk us through, step by step. Like, you woke up one day, you're thinking, we're going to do the link squares thing, and you realize you need to get to know your customers step by step. How did you do it?

Woke up one day, Linq squares. Yada, yada, yada. Enough people told us the general counsel has this problem. They're the ones responsible for this problem. We use cold email.

Cold email.

We bought 25,000 emails of a LinkedIn kind of parameterized search. Like, hey, I'm interested in these 20 industries. I'm interested in these titles. If you can get me the email for these people that have these titles, I'll buy 25,000. I'll buy 30,000 right now. Got the list. Wrote a 4email drip campaign. Very short, very tight. Hey, I'm Vishal. You don't know me. I'm the founder of this company. We're talking to companies that look just like you. By the way, I worked at a company that looked just like you. We had this pain, this business problem, pain around contracts. Will you talk to me? That was it.

How many people said yes?

Hundreds.

Hundreds. How come? Cold email? Why they would say yes?

Because no one emails the general counsel for anything good except for, like, law firms that want them to do their work with them.

Right.

Or bad things going on in the company. So they were just kind of like a nascent hanging around, like, department that no one really emails them to do anything. And here I am just coming. A lot of people were like, please never email me again. That's fine. But, yeah, a lot of people were like, sure, yeah, what's going on? I'll take 15 minutes with you. It's like, hey, 15 minutes. Like, I'm not even asking you for your whole day.

Yeah.

And I said, hey, we're researching this thing and they don't even have anything. But then those discovery calls turned into like, we made a clickable prototype then. So, like, the next people that raise their hand, we could say like, hey, we can show you something. It's a web app. Wink, wink, nudge, nudge. It's not a web app. It's nothing. It's a clickable prototype.

Right?

And then you show the clickable prototype, and then more people are giving feedback like, oh, how does this work? And can you do this? And actually, I try to do this in another system. It doesn't Work, can you do that? Or like that other system doesn't have this thing that I needed to do. Can you do that? We're just meticulously taking notes and aggregating. I mean it's a long year, I mean it was a long year, year and a half of doing that. Then it got to the point where people were like, can I use it? And it's like, you can't use this. This is fake. But you don't know that this is totally fake. Then it's like, okay, let's build it. Let's build a web app. Hired a team offshore. I had experience in this. Hired a team offshore, got a UX designer, made some mock ups, kind of core thesis on the clickable prototype, but actually making it real. And we're off to the races. We started building it, raised some capital, friends and family. My dad, my dad gave us like 25k. It was awesome. We like evaporated it like so fast, like building this software with an outsourced dev team. But it was working. And, and then, you know, by the, by the fall of 2015 we were incorporated and by, by January of 2016, I had quit my job that I was working and my co founder had already gone full time because he was doing the kind of lead gen during the day and the discovery calls. I was building the product nights and weekends. And then we had a product and then it was like, can we, can we sell it to someone? And in April 2016, we got our first customer, pay us 12,000 bucks to use it. We just kind of kept going from there.

What was it like to get your first customer?

It was crazy. I mean, I mean my co founder and I had a lot of experience in sales. Like I had worked in sales ops, he had worked at actual sales customer success. And it was just like rapid learning on like, okay, well you have to go to procurement now and fill out this questionnaire. And it's like, I've never done that. I mean, I know questionnaires exist, but I've never been the guy that has to fill this out. And then we had to do security questionnaire, which was like one of the long ugly ones. It was like a thousand questions. And I just called on one of my friends who was an expert and I said, dude, you have to help me. You have to help me. You have to teach me how to do these like today. Like, please, I'll do anything, man. I'll. Anything. I'll, I'll buy you like a case of expensive wine. Like it doesn't even matter. I need you to help me. And he sat down with me and taught me how to answer every question. Then I probably went on and did three or four hundred security questionnaires. In the years that came, I became a subject matter expert. How to answer all these questions. Subject matter questionnaires.

I love it.

By absolute complete mistake, like I just, I'm then, then the volume is like happening so high at the ends of months and quarters. I trained my CTO how to do it. Eric and him and I are doing it. And I think our all time record is on one quarter and we did like 13 in one day.

Wow.

13 in one day.

That's a lot.

That was great. Yeah. And ye have to do it. And like you don't even know what you don't know about how to get another business to give you money, right? Like you need W9, like, which I was like, I don't know how. What do we just Google it? Like IRS W9, like fill it out. Like put our ein in there. Like you're just like doing it like just in the wild. It's not academic at all. You haven't read like a case study or a blog post. You're just like there. And they're like, well, of course you'll do the questionnaire. I'm like, oh yeah, of course, of course we'll do the questionnaire, send it over. And I'm like, oh my God, I.

Don'T know how to do it.

And it's just, you get better. And then one turned into five that year. We had five customers in 2016. We added another 25 the next year and just kind of kept going.

Incredible. I love that. I love two things about the whole story. First of all, the whole notion about like validating the customer and starting from zero and then how do you get to learn about their them and their needs? Starting from zero and doing it, like you said, meticulously and getting iteration and iteration at bath at. I love it. But then the other side of that, okay, you have a customer, they want to give you money. How do they give us money?

I don't even know what procurement does. And we know it really well now. But like back then, it's like there's just no one in this world. I mean, there's like not a lot of people in this world that will spend time with you teaching this. And that goes back to like the expert kind of model. Like so many people have helped me.

Also the network model, you know, you.

Don'T seem to being in the great ecosystem like Boston, it was just that for me. Yeah, I'm so lucky. I'm so fortunate. I'm so thankful. It's a really expensive place to live. Right. It's the opportunity cost is a lot. The personal burn rate is a lot to live anywhere near Boston. But if you can, then you get access to all these people. It's all about at bats. I mean, that's the greatest story I've ever told anyone. It's like when things aren't going well, just increase the denominator of whatever you're doing. Right. You know, you need 10 customers. Like you're trying to get 10 customers this year. You suck at sales in the early days. And if like I wasn't a sales leader historically and Chris had, my co founder had some experience in it, we weren't like experts in sales. So like, we're way worse than like a real sales expert is. Like, we may need to talk to 200 companies to get 10 out of. So it's abysmal. It's like you're getting a D in school and. And you hope that you could get a C minus. It would be amazing. Like, but you're never trying to make it an A. You're trying to get it to some point where you're like, convince someone to join to take it over for you.

And then making it the end.

And I'm like, thank God. I remember when we hired my CRO now Steve, he came in in 20, 2018. I was like, dude, you got it. And he's like, I got it, man. And I was like, thank God. I never have, I never really have to quote, unquote, think about this like the way that I used to, like I could just give it to you.

Right, right. I love that model and I love the way you think about that. But haven't you made mistakes in hiring? As in, we're going to do this. So tell us that story about that.

Yeah. So much of the early stage journey are like, you have to pick people that can just grid it out and grind and have some sort of built in determination and perseverance because it is terribly hard, you know, and shout out to everyone trying to do it. It's terribly, terribly hard. Because if it was easy, everyone would do it. And you have to remind yourself that. And you know, some of the mistakes we made are just like, we hired big company people too early who didn't get that. You're not going to sit around and manage people. Like you're going to like roll up your sleeves and stick your hand into a muddy problem, and it's going to coat all over you every single day. And there's a kind of a mismatch of, like, we didn't do a great job flushing out and defining because you're a startup and you're a knucklehead and, like, you don't, you know, you haven't written written job descriptions professionally for, like, the rest, you know, all of your life. And you make mistakes like that because you're also in a hurry all the time. Everything is a hurry. We're trying to do everything fast. Like, we need someone to help in customer success. Okay, who do we got? Great. Use a recruiter, get 10 resumes, make 10 phone calls, talk to them down, select. We're down to three candidates. Bring them into the office, chat with them. Like, can you do it? It's like everything behind the curtain is on fire and we're just out front. Like, yeah, no, yeah, it's a really great place to work. Yeah, no, we go out for beers every Tuesday. Like, but the urgency of, like, the needs are, like, it's so great that you make, like, silly mistakes, that it's so stressful and there's so much pressure to succeed and there's so many issues that another human. You're just immediately, like, the day you start, it's like, can you just take all these things? Because, like, I have to go do all these other things that are also in a bad shape or on fire or need fixing. Like, can you take it? And, like, you make mistakes like that when you're going real fast.

Yeah. So how do you recover from those?

Well, you obviously part ways. You learn, you do the whole thing again, but you do it slower. You ask the right questions. I mean, you don't even know what questions to ask, especially when you're hiring in roles that you really don't even really understand. Yeah, Like, I have an appreciation for customer success, but, like, I'm no expert in customer success. Like, I've built on it for a decade. I don't even know what to ask. Right. You just. I don't know. I used to read blog posts like, interview questions. Now you can do it in chat. GPT interview questions for a CS leader. Like, you know, that was the best we had. Right. Because everything is on fire all the time.

Right.

But then you recover, and then you understand that you're much more upfront with the next person you try it with. Like, hey, I want to. I want to let you know, like, this job is Like X, Y, Z, abc. And if this is not your cup of tea, like these are, what are we going to ask you on the first day you start like can you take over all this stuff? And it's good that people opt out that they don't want to do that. And then you kind of center in on people that want to do it. And in the early days you always kind of choose people who just want to grind it out over people you're trying to pay, I don't know, 300k base to that are a quote unquote expert. And then on the revenue side it's so important to pick a revenue leader that matches the selling price that you have. Like the dream is you hire this utopia revenue leader who just comes in and just crushes it. And the perception is like, oh, I picked them out of Adobe or workday or salesforce.com and man, this guy could sell $2 million deals. But if you ask them to sell $20,000 deals, like they, they may not have the right, what I call sales leader, average selling price type of fit. You don't want to make a stretch on either way. Like you're familiar with selling middle market type of software like 20 to 50k. And I'm asking you to sell $2 million deals which take much longer and require 50 touch points and procurement and multi department and a multi giant company. You got to hire people for what your business model is. And I got so lucky. I hired someone who's like a, you know, middle market, small enterprise type of expert and it just worked because it was just like very common for him. He had been doing it for like almost a decade. Like and, and it works. And like you see people make mistakes like that. You can't get obsessed with people work. It's more like forget about the place they work. Even if it's salesforce.com, gosh, wouldn't that be great? And get down into like can you sell at this price point? Tell me how the strategy that you'll put into place to sell higher velocity, lower sales cycles, like 30 days. Can you do $30,000 deals in 30 days? Is that your jam? And if it's not your jam and not your experience, it's not going to work totally because they're going to have to learn how to do it. It's not muscle memory for them. So like you kind of have to pick people like that in all phases of the company. Like what is the need of the company today? Yeah, what does it need in the next couple Years. Can you scale with it? I mean certain people don't scale with late stage companies. Like they're more like a zero to one type crew. There's a whole crew that just loves doing 0 to 1 million ARR. There's a whole crew that's really good, like one to ten. And then there's a whole crew that loves like 25 to 100 or 100 to a thousand million or whatever. Like you'll kind of go through that and some people will just never age out because they're just constantly intellectually curious, learning, leveling up new strategies, getting mentors themselves and. And like that's one of the bigger challenges now is like with the growth of the company there's just very. There's just not a lot of big pool of people that have seen growth from like zero to like, you know, almost 50 million ARR.

Yeah.

It's like you walk into a room and it's like, well, we are the guys now. Like we are the people now who have done it. There are people asking us how we do it. But like you have to. I have to work extra hard finding people who are further ahead of me and be like, will you spend 45 minutes with me and just like, can I just bug you like about how you run the company and what you care about? Because that's how I got here, right? That's how I got here. It's so important.

Yeah. That's how you learn how. How would you say you've grown as a leader, as a CEO, as you. As the company has grown.

Gave away everything. I used to do everything over the years. Not all at once, but over the years. I used to run the product roadmap. I used to decide what we build. I used to be hands on with features and what they're going to do. And I don't do that anymore. I used to work the deal desk at the ends of months and quarters. I used to help negotiate contracts with our outside counsel and be the middle point between my sales team and the outside counsel so we could get these deals in. And I don't do that anymore. Even though I miss it. I love that. That's like fun at the end of a month.

Yeah, I was gonna say, don't you. It's hard to give away things you enjoy.

It is security, the whole security questionnaires, doing security calls with prospects before they buy. And we gave all that up too. And over time that was the plan, is to just give it all away, transition it to an expert, pick a good expert, much better at hiring than we were in the early days. And mostly just think about the future. Like I have to live in next year, what's our next move, what's our next plan? And I can't put that burden on anyone else. I have to get the future right. But this quarter, like what's going on right now, that's something my executive team drew up, drew the plays up, drew the strategy up a year ago or in December of last year, November of last year. And they're executing on it. And I trust that they're going to execute on what they said they would do this quarter. I'm going to help them when they get stuck and poke them when I don't think it's working and use data as a way that we can have an intellectual conversation. And then I'm on to next year. And that's hard, especially when there are places in the business that I know I can help, but I really can't because it's seven layers below me on the org chart and I really shouldn't. But I can tell the executive in charge, hey, I don't like this thing going on in your department way down there. Can you, can you go fix it?

Yeah.

Like I saw this on the Internet and I didn't like it or like I didn't like the way this, you know, whatever blog post was written, can you go fix it? And like I do that. Like I assign like little projects, like go check on, double click on that thing for me. Because like I thought it was like wrong or incorrect. Like yeah, I'm like kind of everywhere and nowhere at the same time. And it's different. It's a lot different than it used to be.

Yeah. Just a few more questions. Two more questions. What do you wish you had known earlier on your journey?

I wish I had known that the perception of raising venture capital was not as highly likely and probable as people would make it out to be in TechCrunch. That you thought maybe venture, early stage venture capitalists would, you know, maybe fund 50, 50 first time founders and multiple time founders, but it's probably like 95. 5, like it's 95, like bets on people they know and have done it before. And you have to be really extraordinarily special to be a first time operator, first time CEO and walk in there and convince people to give money that they're borrowing from other people to invest it in the company. And no one really told me that. But then you gotta take like 100 at bats to get a Couple term sheets and you begin to realize, like, hey, I'm not good at this right now, but I have to get good at it. And I did. I got really good at it. We raised five rounds of venture capital funding. $161 million.

Incredible.

You just get better at it. So. Something no one can teach you.

Yeah. Last question. We're running out of time. 30 seconds. What advice do you have other founders to grow on their journey to grow into leaders?

Got to think about that. You got to think about that framework on the four companies. You know, think about that in the future. Don't give up. Success happens when you repeat things and get better at them. Sales is definitely the hardest if you're slogging your way through. You just gotta keep going. And don't. And don't give up and get obsessed with the solution the customer has. Like, ask people what they want and they will tell you. Ask enough people, you'll have a cohort of people that give you the answer if you're listening and just like, don't give up. Because any journey that's worth doing is gonna be hard. It's gonna be hard.

Beautiful.

But you can do it.

I love it. Thank you so much, Michelle. It was so great to spend time with you.

Thank you so much.

Thanks for listening to From Startup to Grown Up. If you like what you heard, give it a review on Apple Podcasts so other people can find it. And if you know of a founder or someone else who is meant to be on this podcast, drop me a line through my website, alyssacon.com.