How Checkbox Went from Pivot to "Legal Front Door" for Corporations

Hey everybody, welcome to this Founder Institute event. I'm Jonathan Grecian, co-founder and CEO of the Founder Institute. Really excited today to welcome to the stage Evan Wong, who's the co-founder and CEO of a really awesome startup called Checkbox. And I don't want to spoil the story too much, so I'm going to let Evan kind of take the stage here for a minute, but then we're going to get into some questions from the audience. And I know we have a lot of people joining in from today. From all over the world. I know we have a pretty strong Australia contingent here as well because Evan is originally from Australia, now a New Yorker. I'm from New York originally, so, um, and, uh, so that's exciting. But, um, but if you are here, let us know where you are joining in from. This is a totally live event, so we try to get as much interaction and feedback from the crowd as possible. Evan has a really interesting story on how this came to be and how he honestly has built this company now to be at the forefront of this amazing AI revolution that's sweeping all types of industries, but in particular, the legal industry. And I'm seeing here, so, all right, we got an international audience, Bay Area, Palo Alto, San Francisco. So not super international, the first 3 people, but there we go, Pittsburgh. All right. So Canada, all right, there we go. So I know we have people from all over the world here, which is amazing. All right, Melbourne. So we got our first Australians here as well. So like I said, guys, don't be shy. Any questions you have, put them into the chat. Evan's gonna start us off with a quick presentation and then we'll get into a conversation and really start to dig into his journey. All right, so Evan, I'll let you, I'll let you take it away here.

Well, thank you so much, Jonathan. Let me first start by saying it's an absolute privilege to be able to share my story with this forum, with the audience here. As founders, we spend so much time head down building, and it really is a privilege to be able to share the story. So thank you everyone who's tuned in live and anyone who's watching this in retrospect. Whether you're dialing in from Australia or the US or other parts of the world, I'm super excited. I do want to just spend a few minutes here giving you some visuals of the story of Checkbox before we dive into a live fireside chat Q&A with Jonathan here. I won't be able to see the chat while I'm sharing my screen, so you'll have to forgive me. We may have to park the questions after the slides are done. But I want to share a bit of like how Checkbox started and really focus on like where were the pivots that we made along the way. A very, very visual sense. All right, so, you know, Checkbox started, um, all the way back when I was coming out of law school. I, uh, I graduated from a university out in Australia. I grabbed my best friend of many years— we've known each other since the 7th grade, uh, we were 12 at the time— and we decided that sleep was optional. Yeah, we basically didn't sleep for a big part of building the early stage of the company, and we ended up joining the Founder Institute. This is me with the, the then directors of the Sydney chapter, and I was one of the very happy people that graduated from this very challenging program. And we built this company called Checkbox. And the question here is like, how did we get to what we're doing today? It definitely wasn't the first idea that we started with. I think a lot of people have the misconception that you start with some sort of brilliant idea and off you go. No, actually, a lot of times you start with the wrong idea and you make very strategic pivots to get into something that is worth building and buying. So how do we start? Well, before Checkbox, I started a company called Hero. It was in the education space. It was not tech. I wouldn't call it a startup, but it taught me a lot about company building and in particular it gave me an insight that I wanted to build for. I basically found that legal and compliance content was very manual, very static, very painful, and no one liked to do it. And so I came up with an idea. This is the idea that I walked into Founder Institute with many years ago. It was called Compliment. The idea was to have small business owners provide their business and employee data on one side and have, uh, the rules of the labor laws built into the other end. So on one end you have the laws, on the other end you have your specific business data, and you combine the two together and it would create these real-time checklists for you to determine whether or not you were compliant. So gone are the days where you had to read government websites, click into links, try to figure out what you were doing. This tool would basically help you, like, match your specific situation with the regulation to teach you how to be compliant. I thought it was a great idea, and I took it out into market, spoke to a lot of small business owners, and they said, yeah, this is a great solution for a problem we were facing. But I learned very quickly that small business owners, the ones that I was speaking to in Australia at the time, really didn't want to pay for something like this. And it's really interesting because we often, we often think about product market fit, PMF. Actually, there's an extended version of that. It's called the 4 Fits Model: product, market, channel, and model fit. Model meaning how you make money. And in this iteration of Checkbox, the very first iteration, we had decent, like, solution problem fit, but people didn't want to pay for this. It just wasn't the right model. And so we had to pivot. Can't build a company that doesn't make money. So I thought to myself, who is big enough to care for compliance and pay for it, but small enough to still struggle? And so we ended up solving for, for franchises. We thought, oh, franchises has like a head office, they have corporate But at the, at the, you know, at the store level, it's really still just small business owners looking to operate. And so we were working with franchises for a little bit and realized that they weren't that passionate either. And so then we pivoted actually to the tax base. We got a bit of a tip-off to say, well, if you apply tax rules in the system and have people put in their information and for it to automatically tell you how to apply the tax law, that would be super valuable. And so we were building tax software for a while. And really what I was doing at this point was I was reading tax legislation, which for those of you who have never had the, the punishment of ever having to read tax legislation, kind of looks something like this, right? It's like you read a rule that says, hey, this rule applies and this applies but not including these things, and, and, or, and, like, there's a bunch of, like, rules that basically just layer upon themselves, and it bounces you from section 1 to section 200 to section 33, and it was pretty chaotic. And I said, okay, this is a pretty poor user experience. What if we turned all of this into decision trees? And so I mapped all of the tax law into a sequential decision tree where someone could just start at the beginning and flow all the way to the end to an answer. And I would slide this across the table to my co-founder who had just picked up coding at the time, James, and he would code every question, every logic into software. And we built these tax tools that for the first time ever, accountants were really excited. They were like, oh my God, how much does this cost? When does this come out? Can we be an advisor? You know, this was probably a 9-month-long journey to go from the very first idea of employment, pivoting through franchises, and tax to land somewhere where people actually for the first time said, I see value here. But even in the face of traction, we decided to pivot again. We pivoted again because at the time we were both very, very young, inexperienced. We weren't by no means experts in tax law, and we were worried that even though we managed to convince a whole bunch of professionals that this is legitimate software, we knew for a fact that if we launch this into production, there's going to be things that we got wrong, the way that we interpreted the tax law, and we didn't want that liability. We didn't want to build a business that also wasn't scalable because tax law in Australia is different from tax law in the UK and different from the tax law in California, different from New York, and so on and so forth. It's a very non-scalable business because we had to effectively hire armies of lawyers and accountants just to power the content of the software. And so we pivoted. We thought to ourselves, how can we push the ownership and the obligation of the content to the customer so that we as the software company didn't have to own it, didn't have to be liable for it? Is it possible to give that responsibility of the content to our users? And would it be possible so that when the users own that content, they can also create this software automatically without having to code? Basically, could we make my job redundant in mapping out the processes? And could, could we make James's job redundant in having to code any of that? And that's when we conceptualized this idea of a no-code product, this drag-and-drop platform where experts who do this already for a day job that, that run these manual processes use drag and drop and they download their knowledge onto a digital canvas. But this is not just something like Visio or Figma. The moment you map out your mental process, each of these represents a user interface. A business logic, a calculation. It was basically vibe coding before vibe coding existed. How can we create the highest abstraction of coding up to the point where it is visual? And we got really excited about, about this idea. We actually ended up spending about 2 years building this, uh, and eventually launched a product that looked like this, much nicer than the mockup. And we had this really broad vision of solving all problems, not just compliance, not just HR problems, not just tax, but really everything from finance to operations to everything in the enterprise. But any sound founder will tell you that building for everyone means that you're building for no one. And that was very true for us. We ended up getting to about, I would say, a million in ARR, which is pretty good. It's like enough to tell you that something's working, but we really started to hit a ceiling and it was because we lacked focus. And so again, we self-pivoted. We said, how do we actually get more velocity behind understanding our customer? And that's when we went on a journey of figuring out our ideal customer profile. Which ended up being enterprise legal teams. And people always ask me, like, how do you go from this really powerful horizontal tool to solving for legal? Well, we took a very scientific exercise. We actually scored and ranked 20+ of our different customers that were using our product at the time, from HR to it to finance to legal, and we scored them on a whole bunch of different qualities. From reasons to buy, competitive landscape, propensity to spend. And right at the top emerged really two winners. One was in-house legal teams and the other one was actually compliance teams. They were pretty neck to neck with legal just in front. And we thought, okay, maybe we can build for both. But actually, when you look at what each of those parties were interested in, in terms of capabilities and integrations, we found this kind of crisscross pattern which showed us that what one customer cared about was actually what the other one didn't. And building for both meant that we would have to dilute our resources and focuses by two. And so we decided to go with in-house legal. And that kind of brings us to kind of almost where we are today because in-house legal still has a lot of problems to solve for. And in fact, that was one of the key issues. People kept asking us what exact problem were we solving for legal, and we couldn't really answer it until we came up with this really profound idea in an internal paper we wrote about 2 and a half years ago. Uh, we wrote this paper called LSRM, which is really this idea that Instead of using a platform to build thousands of different use cases for legal, which confused the market, like what problem are you actually trying to solve for? We inverted our positioning to say, could we start with the hero use case, legal service management, the legal front door, and back in from that into the power of the platform, but really act as the wedge into the market so that people didn't have to think about this complicated platform. They could just think about this very specific problem that they were facing and the solution that we had. And really things took off, right? I'll kind of skip kind of what the legal front door is just for a second, but like we really decided to then build this kind of service management platform and I'll summarize it here on this screen, which is like when a request comes into legal today, like an enterprise legal team, what Checkbox does is we have AI agents that live in Slack, it lives in Teams, it lives in email, and so on and so forth. And it meets the business where they work. Okay, so this might be a salesperson looking for legal help to review a contract. This might be marketing who's about to launch an ad on the New York subway and they need legal to review the product claims that they're making. They can send an email or a Slack message to legal, and our AI agent will monitor it, categorize it, and say, okay, well, lawyers are pretty expensive people. Let's first solve it with self-service. And if it's a simple answer, the AI will answer that question right within Slack as a reply or an email reply within Outlook or Gmail. And it will read upon the company's policies, playbooks, you know, documents, and just give the answer right there and then. Quick turnaround, 24/7. Sometimes it's more than an answer, it's a process. And so what the AI does is it kicks off the workflow tool, which is really interesting for us because today so many products are AI-driven, and AI is probabilistic, it's non-deterministic. Right, kind of figures things out. Workflow is the opposite. Workflow is rules-based, point A to point B to point C. It's deterministic. When you're working in a large enterprise and with legal teams, some things shouldn't be solved with AI. They should be solved with hard, cold rules. And so we have this ability for the AI to create this fuzzy kind of non-deterministic answer, but at the same time kick off these set deterministic processes. It can generate NDAs, it can register conflicts of interest, handle a whole slew of different compliance and legal use cases. And then finally, if you need people to finally be escalated to, we also have this ability to create what we call matters, which is a fancy word of saying tickets. It's basically ticketing for legal. And this is really what our customers do. It's what Zendesk and Intercom did for customer support teams. It's what, uh, uh, you know, like ServiceNow and Jira did for engineering teams. Checkbox is doing the same thing for legal teams. We're setting up the delivery model across these different modules, and this turned out pretty well. We ended up raising a whole bunch of money across a few different rounds, Sequoia being one of our lead investors in one of our earlier rounds, and then Turing Capital in the round that we just raised end of last year. We found ourselves in front of Times Square painting the streets green, Checkbox green. That's James and I, much older than we were in front of the school canteen, but celebrating Checkbox. This entire cube, three-sided, was playing all day in Times Square. And we found ourselves in Times Square again when the NASDAQ congratulated us on our Series A just at the end of last year here with our New York City team. Today we serve many legal teams, hundreds, many in the Fortune 500 globally. For those of you dialing in from Australia, we service companies like Telstra, Woolworths, Wesfarmers. And then here I have more globally recognized companies that work with Checkbox as well, from your Disneys to your Profounds and your SAPs. So yeah, that's kind of the pivot story. I thought I would make it a bit more visual for you as a start. And then Jonathan, like, I very much look forward to back and forth Q&A with you.

No, it's an amazing story. Can we go back before you, before you close that out? You close it, but can you bring it back? I want, I want you to bring it back because I thought it was a really interesting slide, was the customer scenario checklist slide.

Yeah, yeah, let me bring that up.

So that was— and we got some great questions in the chat. Thank you, Aaron. Thank you, Sean. If anybody else has questions in the chat, please throw them in there. I'm collecting them here, right? But I thought it was super interesting, right? So because this is, this is the part of startups where there's no like one right way to do this, right? So you had And, and for anybody that didn't catch like the whole story there, right, and I, I obviously know the story pretty well, but you know, Checkbox was doing quote-unquote workflows for— and this was back before AI, right, so like no-code workflows for all types of businesses, right? And like you said, you were doing a million ARR a year. It's a pretty decent business. Um, but then you got to the point where, you know, you guys weren't satisfied with set, right? And we can get into some of those decisions in a second, but I thought this was a really interesting way where you started to see, okay, well, we have— I mean, how many different— okay, you had 20 different scenarios is basically what you're saying.

Yeah.

Across all different kinds of industries, across all different— not even just industries, but departments within those industries. That's right. Yeah. And it was probably like spreading you guys super thin, and then you basically fired up the spreadsheet and you said, okay, let's start to score these. And what I thought was, it was super telling here, right? It's not just like scoring them, okay, how much money are they paying us or anything like that? It's more, yes, pricing is part of it, but it's like how distribution channels, how easily can I reach them? Right? How competitive is the space? How positioning? I'm assuming when you say positioning, it's like sort of your ability to kind of speak to them really easily with your positioning. Is that kind of what that column was?

Yeah, exactly, exactly.

Yeah, so I think this is a really interesting thing, and it's, it's something that happens at— it's funny, right? I mean, you guys have been around for 9 years, but this is something that you see a lot of like very large companies do all the time, right? Because people think of this product-market fit thing as like a destination, but, but the market is constantly changing, guys, right? So literally, you could have— you tomorrow, you may be like, we got product-market fit, but don't like pop that champagne because the world's going to change the next day, and then you're going to have a little bit less and a little bit less until you continue to pivot with the market, right? So I thought this was super— did you grab this template from anywhere, or was this just something that you kind of hacked together?

I think we created it from first principles, if I'm being honest. Um, we tend to be a very first principles company, so a lot of the frameworks and the thinking we create just inwards.

Okay, yeah, I thought this was really interesting, guys, because it's, it's the same kind of thing. Like, even— so you guys were 9 years in, you had paying customers, but it's very similar exercise that we see too with new founders when they're doing initial customer customer development, right? Because I always see in the beginning, it's, it's a very common mistake for founders to— they always try to go a little bit too broad, right? Now, you guys had paying customers, so I, I can't fault you for that, right? But it's like a lot of people will in the beginning, it's like, oh, I want to help, you know, businesses do X, Y, and Z. And it's like, no, you, you gotta try to niche it out a little bit, right? But yeah, so that was— I wanted to bring that up because I thought that slide was really, really interesting. And people were asking like, yeah, where can I get this template? Because I think that's— it's an important thing. It's really, really hard to discern if somebody is paying you money, right, to start to say, you know what, I don't want your money.

Yeah.

Right. I mean, you do want their money, but you know what I mean.

It's so hard. It's really hard though, Jonathan, because You know, like if you just reach far and far enough, someone at some point will want to give you money for your product. But that's not necessarily good because, and it's the hardest thing truly at the beginning to walk away from revenue because you need to find revenue that actually compounds, right? That actually scales. And that comes with focus. Yeah.

And I found in the beginning too, right? Especially in the early stages of entrepreneurship, if people are willing to kind of return your phone calls and talk to you and stuff, right, you start to almost feel like, oh, like I owe it to them, like, oh, like they get me, like they're, they're a, they're an early adopter or something, right? But it's— but you have to have that laser focus, like, like you showed on that document, right? It's not just about who will pay you, it's about, okay, like, are these people reachable at scale? Um, do they actually have the budget? Um, are they you know, really fitting into something that's kind of neatly organized that I can build a business around, right? And I, I'm going to get to a couple of the questions here, and anyone else in the chat, please do put your questions in. But another thing that I also just wanted to point out too that I thought was really brilliant was, you know, you said that to start with the, the hero use case and then build a platform from there, right? And that hero use case for you, and I just know this from, from obviously following you guys for years now, right? You guys were all about, okay, like, we have— we'll use our software and you can automate your workflows, right? So that, like, all types of workflows, right? So then you started thinking about, okay, not about all the workflows, what is like the workflow? Yes, essentially. Yes, right? And In defining the workflow, that was basically saying, okay, who, in what scenario do we become like this hero to our customer? And that was essentially where, I mean, was that like, what, what spurred that decision for you guys to really go into that level of focus that led to the pivot towards enterprise legal? Um, was it like, was it pressure from investors or was it just, you know, conversations that you were having? I mean, I'm just curious of how that urgency kind of came up?

Yeah, it wasn't from investors because you have to remember that ultimately you are the operator and you have the most context of the market, more than the investor. And so these kind of critical strategic pivots, you're not going to get from your investors, right? They can give you feedback, but it comes from within and it comes with really being in tune with the market. It came about because For us as a very powerful workflow tool, like we were in this weird situation, as you said, Jonathan, where we had a million ARR and that's enough to give you some false sense of signal. But I would say that if when you're building the company, whether you're at $100K ARR, a million ARR, $10 million or a dollar ARR, if you're feeling like the acquisition of customers is extremely painful, that you're like literally like really just forcing through brute force the next dollar, you probably should question your like, like the actual approach that you're taking because there are definitely— it's kind of like there's always a, there's always a smoother way, there's always a faster, easier, lower resistance way to revenue. And so if it feels very high resistance, you need to challenge your underlying assumptions. For us, like we kept getting the same signal. We love the product. It looks very interesting. I just don't know how to use it. I don't know what problems to solve with it. Like there was this disconnect between excitement and buying. And so we really had to challenge ourselves in the same way that we went from multiple departments to just legal. Even within that shell, we said, well, within legal, instead of hundreds of use cases which we know the product can solve— and that's a hard thing, it's walking away from opportunity— even though we know that it can solve hundreds of problems, we said, what's the one problem that simplifies what we build so that the buyer can very easily associate that with a problem and just simplify it for them? You actually— it's crazy how simple you need to make products and positioning for enterprise buyers to, to buy.

And that workflow that you described there, where it was literally like, okay, this type of user, they get this type of thing, then they, they send it to here, and then it treats it like this, right? Then I really liked at the end, right, it was probably followed, I'm guessing, your discovery process, where then you started to see, oh, like, we're literally doing the same thing for in-house legal that, like, our ticketing systems did, right? So then you start to see those parallels, right? And that story is really what helped you connect to that audience. And it's, yeah, I don't, was it an aha moment for you? Was it like conversations that you had? And, and because I, I know it's, and I've been in the scenario before, right? It's not easy to get that, you said that juxtaposition where you start to, you're selling something and people are like, oh, it's super cool, right? And you're probably focused on features and you're showing them, oh, our platform, we can do this, this is cool, this is cool, right? And then they're in their head like, wow, this is super powerful, but it's still that disconnect between, okay, well, like, how does it exactly make my life easier or get me closer to my KPIs, right? But you were able to finally get there by just simplifying, it sounds like.

Yeah, you, you get that insight by literally speaking to as many customers as you can and doing, and doing pattern recognition. And not holding onto your idea too tightly. I think too many founders hold onto what they believe they should build and the market's basically screaming at them, telling them what to actually build and they can't hear it cuz they're holding so tightly onto what, what they thought they should build. And so I'd say like, you can't go wrong if you just speak to like 200 of your prospective customers and you just literally listen to what their pain points are and you map it and you, and you summarize and you synthesize and then The answer is there. And it's crazy because as you kind of drill down, you might be thinking, well, I wanna build a really big business and you drill down from multi-segment to just legal and then multiple workflows to just one. As we're building for this one workflow, I mean, oh my God, the depth of just this one thing is so deep that we genuinely think we can build an incredibly large business just from this one use case. And to think that we were trying to do like macro levels of exponential you know, magnitudes larger. I mean, that's why we weren't successful. Like we are solely focused on this one thing and it's already so deep and has such a big market size. And so you need to get to that level of clarity and you get there by speaking to customers and synthesizing their feedback.

It makes perfect sense. And it is, it's still like, it's one of these things that you hear as like literally what we're going through something similar at Founder Institute right now where we were, we had a product for like governments and again, it was the kind of thing where we were like trying to do too much and I were like, no, like we gotta do this, right? So even at Founder Institute, like it's something that you constantly hear people telling you and you're like, yeah, yeah, I know I gotta do it, but you really have to kind of break through there. And so Sean was asking a question like, as you were going through the pivots, how did you know the difference between the signal to stay the course versus to actually change direction? And I think you answered this a little bit where, okay, if you're going through the sales process, And you said it was painful, right? Like, how would you quantify the painful? Like you said brute force. So it's like, okay, you're constantly the person following up. Like they're not following up with you, you're following up with them, right? Maybe you're getting a sale, but again, it's like maybe not at the dollar amount that you wanted and or to the level you wanted, but you've worked so hard at it. Maybe there's some personal relationships that they're saying yes and they're signing on the dotted line, right? But like, are there any other anecdotes you can give there as the see, like, you know, yes, it's— you, you have some form of traction, but how do you know that, like, maybe this isn't the right traction, or that you're not talking to the exact customer that's really going to make things that smoother stream, as you, as you mentioned?

So first thing I'll say, and I don't, I don't know where everyone's stage is in terms of their company building journey, but if you're trying to still figure out PMF, this is founder responsibility. If you have someone in between that you're delegating this to, if you have a salesperson, a head of sales, a marketing person, like you have to be at the coalface of customers because that feedback loop and how tight you make it is how you're gonna find PMF. Okay, so that's the first thing. Like if you're not doing this yourself directly, make sure you're doing it yourself. Now once you're doing it yourself, because that's what you do first, and then once you find it, you scale out. Then you teach other people, you scale out. But finding PMF is a founder's job. Once you do that yourself, I can tell you what the right signals feel like because that's immediately obvious. If every person you meet starts to describe the same thing in the exact same words and you can literally predict what they're going to say before they say it, And this happens 99 out of 100 times of the people you meet, you found something. If you don't, keep pivoting. Because I can tell you now with Checkbox, we know exactly, exactly when a lead comes in, when we speak to a customer, we already know what they're going to say. We let them say it because that's how sales works, right? But we already know exactly what they're going to say. We already know their concerns. We already know everything about the customer and it's the same every single time without fail when they're describing the problem space that we're solving, that's when you know you've found PMF. If you don't have that, you gotta keep pivoting.

Now, yeah, that's— And you said it was, there was a quote here from a recent talk that you did people think that achieving product market fit is a moment in time, but it's the keyword, the markets. The markets are changing constantly, right? So for, for you guys now, like, so you found this, this product market fit, right? But again, it's always tenuous. Like, something could happen, a new model could be released tomorrow, it could be released right now, we don't even know, right? Um, so, and, and I, and I love that you brought up the point of always staying in touch with the customer. Um, like, I, I do calls with founders, with applicants, the Founder Institute, still to this day, for example, right? Just, just because, again, if I, I feel like if I, if I'm not talking to those applicants, then I'm just gonna like lose track of the customer, right? But so, are you— you're still getting on a lot of these sales calls all the time?

Like, oh yeah, yeah, yeah, yeah, it's so important. Conferences, sales calls. Uh, you have to be close to the customer. The moment you lose that touch, uh, you're screwed. So yeah, you got to be really, really close to the customer for sure.

Aaron was asking, so you're not an attorney, right? Are you? I don't think you are.

No, I mean, I went to law school and I came out of it, but I'm not, I'm not, you know, I never practiced. So, okay, well, you've never been my customer. I've never been my customer, correct?

Sure. I, I think her question was more like, how did you, did you find that as a as a detriment to getting into the legal market? You know, like, how did you break into the legal market? Did you feel like there was any kind of like credibility gap there as you, as you went into that market? And I think it's probably a good question that can apply to any business too, right? If you're not actually coming from that business, you're sort of an outsider, so to speak, trying to solve somebody's problems. Like, was that a, was that a gap that you had to cross?

I think it's a strength and a weakness. So like most things in life, you have to make most with your situation. It's a weakness because lawyers really do favor and immediately sort of respect other lawyers because they sort of understand each other from the get-go. So, you know, my law school background gives me like half a point in that direction, and I do leverage that a lot in presentations and customer conversations. It does still give me that half a point.

You might as well bring it up, it can't hurt, right?

Exactly. Uh, but the strength I would say is when you come— so here's the real, here's the real thing. There's something called founder, um, founder product fit, right? You talk about market, uh, product market fit. There's also founder market fit, founder market fit, which is are you the right founder to build for this market? And I wouldn't think of it as much as credibility as it would be empathy for your user, right? Like, if you were a software developer building a dev tool, the ability to build a great dev tool is going to be much higher than like a non-technical user trying to build a dev tool. Just, just that kind of just makes sense, right? So same thing happens if you're a lawyer building for lawyers. Naturally, the empathy is just going to be intrinsic. That comes as a double-edged sword. I was never an attorney. But I built a great product for attorneys because when you're an attorney, you have a very myopic view. Your own experiences color what you think you should build. And sometimes founders have pretty headstrong visions about how things should be built. Building a great company and product is not about building a product for yourself. Okay, that's kind of what vibe coding is today. You can build a fantastic productivity tool for yourself. But to build a great product for the market where you're gonna have 1,000 customers and $100 million in ARR, that is not your experience. That is the market's holistic experience. That takes a very disciplined mind to be able to synthesize again and be open-minded and, and think about all those things. And so it's a double-edged sword. Like I think that one of our strengths coming in was we were a clean slate. We were a blank canvas. and we would just be a sponge to learn as much as we could about this space and build the right product for, you know, 1,000 people, not 1,000 companies, not just, not just one. So, you know, pros and cons. But generally I think founder market fit is a good idea. We didn't have it, to be honest. So we were a bit of the underdogs coming into this.

And I think like you said, if a founder can show empathy and we've seen this time and time again too, Right? If, if a founder can come in not as like trying to be some hotshot know-it-all, it's just like, no, I, I, I see your pain, I feel your pain, and I'm here to try to fix it. Um, it can— it, at least in the early conversations, it can really go a long way, right? Because sometimes that naivety in the beginning is, is— can be an asset. Now, over time, maybe it could, you know, but as you start to grow, then you things like compliance and things come into play. But that's sort of a, that's a tomorrow problem, right? You can, you can cross that bridge. Now I want to bring up another quote that I, that I saw that you gave, which I think is really informative too. And it's pretty related to this. It's just that like customers are experts in the problem, but you need to be the expert in the solution.

Yes.

Right. So I think, and I don't want to dig into that a little bit as well. Like, as you now— you've had 1,000 conversations, probably more, with your target market, right? To the point where now you know what they're going to say and all of that. How did you really dive in, understanding, okay, they're experts in the problem, right? And then to be Are there any tactics that you can give to any founders here as to, you know, just, I don't know, the different ways that you handled some of those conversations in the beginning, maybe when you didn't have credibility in order to then build this perfect solution that you guys have now created and then are creating?

Yeah, it goes back to humility and being curious. I think when you try to sell too early before you have credibility, before you have understanding of the customer, They can see through it, but also people don't like to be sold to. You know what people like to do though? They like to give advice. They like to help.

Yeah.

Right. It's just part of human nature. And maybe, you know, it's a break from their day job. Maybe it's a form of recognition that they have value to add outside of, you know, their career. And so as a founder, when you approach a conversation with a customer, like a potential customer, and you say, hey, actually I'm not trying to sell you anything, I'm just here to learn from you because I think you've done some great work, you've written some interesting things on LinkedIn, I'm actually building in the space, I'm trying to solve this problem, I have a hypothesis. When you approach with that angle, you'd be surprised how many people will give you their time. And there's little hacks that you can do in the early days as well. If you have just a little bit of capital, you can actually use things like LinkedIn ads but not display ads, like the kind that actually automates emails to a specific demographic, right? So you can set all of your parameters to say, I'm interested in talking to, let's just make it up, you know, directors of finance and CFOs of companies with 1,000 people plus, and you set your demographic parameters and then you basically write a templated message to the effect that I just described, which is I'm not here to sell, but I'm here to learn. And you, and you like, if you really wanted to do that scale, you could hit, you know, I don't know, like 200 people on LinkedIn. And, you know, I'd be really surprised if you did not land 20 meetings out of that with the booking link in there, or, you know, and then all of a sudden you have like people to speak to. And then if you run the meeting right, they will be invested in you so that the next time when there's development and you do a follow-up, you say, hey, thanks last time for the conversation. Learned a lot. In fact, I've made phenomenal progress since then. I've now gone ahead and built XYZ based upon your feedback. Would you like to take a look? They're obviously going to say yes because they're now invested in, like, you know, people love that feedback loop of I've given you advice and you've done something with it and you've come back to show me. I mean, at some point they're just going to say, how much does this cost? And you convert basically early conversations and signals into trust. Customers. Um, so, you know, that's, that's a little bit of a hack for the, for the early days.

But you got to do the work, you got to get on the calls.

Oh yeah.

And this is, this is where it's— I know now you've been in the founder game for so long, right? But it really is, it's one of the things that we see with early founders, they're trying to take shortcuts, right? They'll start to send out a survey or something like— no.

Oh no, oh no. You gotta get out there.

Yeah, you gotta get on those conversations, gotta have 20 of them before probably you can even start to spot any kinds of patterns, right? And like you said, then you start to see the patterns, you start to understand their language, the ways that they're phrasing things, right? And now you start to speak their same language, and then you can start to project, oh, I know what you're going to say, right? And then you can start to build those hero workflows. So Keith was asking, so Checkbox, if I'm right, Checkbox didn't replace any existing platforms. It's more of like an incremental spend. So how did you convince customers, you know, to find quote unquote like fresh budget? Right. And I think it's an interesting question when it comes to like enterprise sales, because it's not, you weren't going in saying, oh, we're going to replace this other thing that you already have earmarked money for. Right? This is a new concept, this is a new thing, but it's going to provide all of these values or all this value to you, right? But there is a different— it's a different kind of conversation. So I think it's an interesting question, you know, how did you get over that, that bridge?

Yeah, thanks, Keith. It is a very good question. And this is the challenge with category creation, okay? So some of you are going to build into existing categories. Maybe you're building the next AI-powered CRM. Every company's probably got a HubSpot or a Salesforce, and you're trying to displace that budget. When you're category creating a new category, you have to create new spend, new value. It's actually much harder. So how do you do this for enterprises? The answer is really twofold, I would say, right? So in a sales process for enterprises, I always think of it as two steps. One, you're convincing your immediate buyer, who usually you would tag as your champion, that they want to buy your product. Like, you want to— that first phase is about selling so that they want to buy and they're convinced they need your product. That sounds like the whole thing, but it's not. In enterprises, there's a second part, which is once they've decided that they want to buy your product, they then have to make the sell internally to the rest of the organization as a committee, it's almost like a proxy sell. Usually they have to sell it on your behalf internally to the CFO, to the CEO, to the CIO. So you got to sell twice. The first half to your champion and the second half your champion's doing the internal sell. Your question actually hits the second half, right? So when you get to that second half, how do you create fresh budget? The answer is you cannot rely on your champion to do this for you. You need to Build a business case. It's basically the answer, and you have to do it. You have to build the PowerPoint, the ROI model, the calculations. You have to collaborate with your champion so you make it business specific, and you basically say, hey, if you spend $100,000 on Checkbox— making this stuff up, by the way— if you spend $100,000 on Checkbox, you will get $1 million back over 2 years. That's a 10x, you know, ROI. and the numbers need to be defensible. And, you know, either you tie it to avoidance of cost, either you tie it to generation of revenue, or you tie it to increasing the velocity of revenue, reduction of risks that result in fines. Like, there's many ways to quantify the value of your product, but you effectively build that model for your champion. They sell it internally. And that's how you get fresh budget.

And that's, that's where things like pilots and stuff too, with that champion, smaller things to build, to build that, that business case. But yeah, it's, and that's, it is the harder thing to do, but that's typically where the most opportunity is as well, right, Evan? I mean, yeah.

Oh, absolutely.

I mean, even in the earlier iteration, were you guys displacing other budgets with when you were just doing more generic workflows, or even was that still new budget back then? I'm just curious.

Yeah, it was always new budget for us actually, so we had to get really good at that. You know, the thing I've learned about company building is the grass is always greener on the other side, but every path is really freaking hard. Like whether you're trying to displace or whether you're net new, it's just got different versions of hard. Because if you displace, then the compete is very different. There's already existing user expectations, feature expectations, there's an existing budget, so you're siloed into that bucket, right?

Like there's, there's all these other problems, but the rules, but the rules of that playing field are sort of defined like you said. So at least you know the rules and you can sort of, oh, okay, like if I just go, you know, 10% cheaper, I may win this deal, right? But when there's no rules defined, it is a lot more challenging. But it's a bigger— it's a— it's blue ocean in some cases, right? But yeah, it's just challenging. You're sort of making up the rules as you go along. Um, so Ash was asking here, um, you know, if you were starting over— and we're going to be coming up on time here too, so I want to go, you know, kind of get also a little bit back to the meta component of this where it's like 9 years in you guys, you've been— it's not like you've been struggling this whole time. I mean, you bootstrapped it for a couple of years, you've gone through a couple of different iterations, but you guys have had revenue and customers for a long time now, right? But now it's like the world has changed and you've done this pivot and it seems to be really, really well-timed. And it seems that, you know, there's a lot of reasons out there to be like super bullish on what you guys are doing right now. But Ash was asking, like, if you were starting over now, Like, I guess it's sort of a trick question, right? It's like, well, AI didn't exist back then, or at least not in its current sense. But you, you clearly had to kind of go through some of those early lumps, right? You wouldn't have all of this perspective and stuff that you have now if you didn't have all of those early conversations and worked with early customers that maybe weren't the right customer even though they were paying you, right? But in the long run weren't the right customer. But You know, with the experience that you have now, is there something else you would tackle first or that you would do differently or that you would approach differently in selling the product?

Yeah, I think the big, honestly, the biggest learning that I would have done differently in the early days is be more proactive about finding PMF and chasing it. I think founders, including myself, become very passive about, let's just build a product behind an inkling of an idea, and if I build a really cool product, then eventually it will work out. And what I found out, like, with the more recent years of our success is PMF isn't something that just, like, lands in your lap. You have to, like, you have to basically continuously pursue it, find it, and, and, and, like, really like just laser lock on sight of it. And I think we spent too much time trying to build a company and not enough time trying to find PMF so the rest of the company building journey would be easier. Like truly. And like you said, it's not a milestone. Well, it is a milestone, but it's not a static milestone. Like once you find it, the market is always changing. And in today's world, the products are constantly changing with how fast AI is developing. And so the P and the M are like changing.

So you constantly have to have faster than they ever have before with more competition than they ever have before. Someone's in their garage right now just like 5 coding a product and maybe pitching it. You know what I mean? Yeah. So it's, it's the stakes are just going up. But I, but I love that too where you said like a lot of time, like company building, right? So it's like, oh, building a team, trying to build a culture and all this kind of stuff, right? But at the end of the day, it's— if you don't have that product-market fit, like, you know, as a, as a founder, you need to focus on the things that have exponential impact. Yes, right. That product-market fit's going to have exponential impact on everything else in the business.

Yeah, we spent— this is the takeaway, which is like, we spent too long at certain points in our company journey building for the wrong thing, right? And it's not that it's zero results, it's just like enough results to be like, oh, maybe this will work. But no, like you want to basically continuously challenge yourself to make sure that you're building the right thing. So there's a compounded effect, you know, to what you're building. So constantly chase PMF, have a relentless like threshold for that. And yeah, it's like, again, if you're wondering, oh, but Evan, like how do you get there? The answer was in this webinar, continuously speak to your customers, listen to what they say, find patterns, synthesize, and just find the lowest resistance path to people wanting to buy and use your product. That's how you get there.

So I'm gonna cut up the— where Evan literally walked through, right? It was that one slide, couple components. Where it's like, here's the hero's use case, right? And that level of specificity. This type of customer does that, then they send it— I forgot, was it Slack or whatever the tool was, right? Then they send it here, then the platform does this, it helps them with these 3 things, right? Like that, I'm imagining there, that is probably— is that the core component now to your guys' sales pitch when you're talking?

Yeah. Yeah, yeah, that's a very—

that was refined over thousands of pitches, right?

That's right. Yeah, that's right.

To get to that level of clarity, that hero's use case.

Totally. And look, I, because of the, you know, this audience is obviously not our customers as an audience, and so I skipped a lot of the slides, but really even in our sales pitch deck, a lot of the slides are around framing their situation, their problem, the market and how we fit in the competitive landscape. And like, you should know it so dang well that when someone goes through it, they're like— and we get this all the time— they're like, oh my God, are you sure you guys aren't a general counsel? Like, how do you understand us so well? I've never felt so seen before. These are the words that come out of people's mouths when they sit in our sales meetings, right? Like, that's where you want to get to.

Yeah. I never felt so seen before, right? It's like, wow, you're actually speaking my language. You understand my pain. And you're doing something about it. Right? So there is— and if anyone has a final question, please— and we will be doing a recording of this. We'll share that with everybody along with that presentation that Evan gave. Because I thought that was great. Evan, honestly, just breaking it down into that simplicity. And there's a lot of complexity in that simplicity, right? It takes a lot of time and hard work and conversations to get to that level of simplicity. But once you can, that's really where the light starts to come on for a lot of the customers that you're talking about. Is there, for founders that are starting up right now, okay, so you started up back in a time and wow, it's 9 years ago. Founder Institute's turning 17 on Thursday. Actually. So we're old as well. But yeah, 9 years ago in your space, right, where it was back— was Zapier around when you guys started? I'm just thinking like in terms of like the no-code tools movement. I might have been, right?

Yeah.

Yeah. But it was like, you know, it— when you guys started, it was a lot of, okay, it's like software as a service, but then it was a lot of drag and drop interfaces, right? It was kind of that time. Um, and now it's just like insane, like how— where all the leverage now is, is less. Like, like we said, somebody can vibe code a product super, super fast, right? So the real value that founders can bring to the table is exactly what you've been showing here. It's, it's just the, the grind. It's the ability to talk to the customers and to, to make them feel seen and to solution because the building is becoming easier and easier and easy. Now I know as a business you guys are, are, um, you know, you're in a super lucrative industry, you're becoming the legal front door for enterprise legal, right? So there's a lot of reasons where you guys are going to have a lot of staying power there. Um, but for, for new founders, I mean, do you have any advice on, you know, like let's say that you woke up today and you knew about this use case but you didn't have a product, right? Would you— how do you think that would kind of change your approach if you were starting this business today, um, based on just all the, the things now that founders have at their disposal that you didn't have 9 years ago?

Building software has become cheap and extremely rapid, and you need to use that to your advantage. So I would say like The ability to test and iterate is extremely fast. Also, product as a moat has eroded significantly. It's all about now knowing what to build. Because when product is cheap, when product development is cheap, it means that you can also have the risk of feature bloat, building just gunk into a product that ultimately is low quality because it doesn't actually solve a real customer problem in the best way. That I should. So what has changed? The speed in which you can develop software. What has not changed is how maniacal you have to be about understanding your customer, solving their problems, customer empathy, making good product decisions, making good user experience decisions, um, and being very good at just expressing what you want, because that's effectively how these AI agents, uh, are going to do their work. Is being very good at communicating now, not just to humans, but also to AI. And just leveraging that fast feedback loop that is in your hands. So that's what I would do differently and what I would do the same. Actually, a lot of the fundamentals still the same, but the way, the speed in which you can get there, that's different. And as you build and scale your company, that moat of product development needs to be shifted to things that AI agents cannot touched today, which is things like building brand, credibility, trust, relationships, data moats, like data flywheels. Think about your data strategy. Like all of this becomes the new moat in building software companies. So yeah, it is very different and the playbook's different now.

Yeah. But even like if with the ability for people, like you said, the feature bloat, right? For more products to come out, for people with existing products, you're like, oh yeah, we can throw this little nifty, you know, shiny ball on here, and this one too. Oh, one customer wanted this, sure, let's throw that on there, right? Yeah, like you said, that, that makes it even more important if you're trying to actually build a great product to have that level of focus to get rid of all that crap, right? Yes, people don't want all of it, they just want what they, what they need. And exactly, yeah, it's That's the founder's role, I think, now as we, as we move forward, is to try to not become like the next, like, Salesforce or something, right? Where it's just like throwing just things on things and things on things and things on top of things. Like, there's gonna— things are going to get, um, divided up across industries and stuff, but still there's going to be never-ending opportunities to just niche and just do one thing really, really well and focus on that one customer.

That's right, spot on.

Okay, well, thank you so much, Evan. Thank you everybody for joining. We'll, we'll send out the, uh, the recording in a couple of days here. Uh, if you guys don't follow Evan, please do. I, I put his LinkedIn in the chat here earlier. We'll share it again right now, and we'll share it in the, in the follow-up emails. But Evan's one of, one of the fastest growing companies in the Founders to Portfolio right now, Checkbox. Legal Front Door for the AI, or, uh, the front— the AI front door for the enterprise legal industry, uh, and doing amazing things from Sydney, now based in New York. One of the most supportive mentors of Founder Institute. Thank you, Evan, for everything that you do to support our network, and, uh, thank you for taking the time tonight, man.

Of course, Jonathan. Now, this is a really fun chat, and again, the Founder Institute was very much the beginning of our journey. And so wherever I can give back to everyone here, I would love to. So good luck with your respective journeys. This is, uh, this is a wildly challenging journey, but one that is just irreplaceably, uh, rewarding. So good luck building, my friends.

All right, appreciate it, Evan. Thanks everybody, have a good night. Talk to you all soon. Bye.