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Checkbox AI CEO Evan Wong: How to Build Enterprise Software That Scales.

February 23, 2026 · Hosted by Dexter Cousins

How Checkbox AI CEO Evan Wong Built a $100M Legal AI Company in 9 Years

Checkbox AI CEO Evan Wong just closed a $23 million Series A at a $100 million valuation. The journey from bootstrapped startup to serving over 100 enterprise organizations—including SAP, PepsiCo, Telstra, and Woolworths—took nine years, three funding rounds, and a strategic pivot that changed everything.

On this week’s Fintech Chatter podcast, Evan shared the lessons learned building Checkbox AI from stealth mode to becoming the “AI Legal Front Door” for Fortune 500 companies.

The Strategic Pivot: From Multi-Sector to Legal AI

When Checkbox AI launched in 2016, the vision was broad: a no-code platform that could automate workflows across any business function—legal, HR, compliance, procurement.

The product worked. Early customers found value. But scale remained elusive.

“At some point, we made the decision to go from being a platform that could serve multiple functions to focusing purely on legal,” Evan explained. “That’s not easy—you’re essentially choosing to walk away from potential customers and revenue.”

The pivot unlocked growth. By positioning Checkbox as the AI Legal Front Door for enterprise, the company found product-market fit with in-house legal teams struggling to manage increasing volumes of requests from business units.

Today, at Hitachi, 83% of routine legal and compliance requests are partially or fully automated through Checkbox’s platform—freeing legal teams to focus on high-value, strategic work.

Building for Enterprise From Day One

Most SaaS companies start mid-market and struggle to move upmarket. Checkbox AI took the opposite approach, targeting enterprise customers from the beginning.

“We dealt with the pain upfront,” Evan said. “Had to do SOC 2 early. Had to build robust features for enterprise at the get-go.”

The strategy paid off. Today, Checkbox’s average sales cycle for Fortune 500 companies is approximately three months for six-figure USD deals.

But building for enterprise requires discipline around product development. With large customers comes the temptation to build what they ask for—not necessarily what the broader market needs.

“Take everything from a customer as a data point, not as an instruction,” Evan advised. “Customers are experts in the problem. You’re the expert in the solution.”

The $23M Series A: Touring Capital, Peak XV, and Strategic Angels

Checkbox AI’s Series A round was led by Touring Capital, with participation from existing investors Peak XV (formerly Sequoia Capital India) and Tidal Ventures, plus new investors Conductive Ventures and Five V Capital.

The round also included Jerry Ting, VP and Head of Agentic AI at Workday, who was formerly Co-Founder and CEO of legal AI company Evisort.

The capital validates Checkbox’s approach to legal AI: rather than building standalone chatbots, Checkbox embeds AI agents directly into enterprise workflows—email, Slack, Microsoft Teams, Salesforce, and intranet portals.

“As more legal work becomes AI-assisted, the winners will be the platforms that can route requests intelligently, integrate across the legal tech stack, and turn institutional knowledge into scalable workflows,” said Evan Wijaya, Principal at Touring Capital.

Competing in a Market with $5B+ Valuations

Legal AI is attracting massive capital. Harvey raised at a $5 billion valuation. EvenUp hit $1 billion. How does Checkbox compete?

“It’s actually a good sign,” Evan said. “Higher tides raise all boats. There are billions of dollars in productivity to be unlocked in legal.”

Checkbox differentiates through its focus on workflow orchestration and enterprise integration rather than broad AI assistants. The company was named in Gartner’s 2025 Hype Cycle for Legal Tech as category-defining infrastructure.

The Nine-Year Journey: Bootstrapping to Series A

From founding in 2016 to Series A in 2026, Checkbox raised only $6 million USD before this latest round, remarkably efficient for a company generating eight figures in annual recurring revenue.

The timeline included:

– 2016-2018: Bootstrapped in stealth mode, founders not drawing salaries

– 2018: $1.77M angel round

– 2022: $6.3M pre-Series A led by Sequoia India’s Surge and Tidal Ventures

– 2026: $23M Series A at $100M valuation

“Australian companies are really good at building with a frugal mindset,” Evan noted. “Coming to the US, investors are always impressed with how efficient we are.”

Building with AI-First Mindset

As Checkbox scales from 75 to 100+ employees, the company is embedding AI-first thinking throughout the organization.

“Do you first jump to hire someone when you need bandwidth, or do you consider what AI tools can give you leverage?” Evan asked. “That order of operation in your brain—that’s the mindset we’re building.”

AI proficiency is now a hiring criterion. Every team member is expected to leverage AI tools to increase their output and impact.

“There’s companies like Cursor who have gone to really big scales of revenue with very lean teams,” Evan said. “The tools are there now. It’s about leveraging them.”

Lessons for Enterprise Software Founders

On Product-Market Fit

“People think achieving product-market fit is a moment in time. But there’s a key word—market. And markets change constantly. You have to keep chasing it.”

On Customer Development

“Customers often explain what they want in solution form, but they’re not the solution experts. You’re the solution expert. The customer is the expert in the problem.”

On Strategic Focus

“Who are NOT your customers is just as important as who ARE your customers. That gives you clarity in who you want to build for.”

On The Long Game

“Most startups either scale much faster or they die. We sustained the business through a longer timeline by building efficiently and staying focused on enterprise customers who could deliver meaningful contract values.”

What’s Next for Checkbox AI

The Series A capital will fund two primary areas:

1. Engineering, product, and design: Expanding the team primarily based in Sydney, Australia

2. Go-to-market: Scaling sales and marketing to compete globally

“We want to become the cornerstone technology for enterprise legal teams,” Evan said. “You wouldn’t start a sales team without Salesforce. You shouldn’t start a legal team without Checkbox.”

Hiring Enterprise Software Leaders?

At Tier One People, we specialize in placing executives who can scale enterprise software companies from Series A to market leadership. 

Whether you need a Chief Revenue Officer who understands enterprise sales cycles, a VP of Product who can balance customer demands with strategic vision, or engineering leaders who can build for scale we connect you with the 1% who define what’s possible.

Contact Dexter Cousins: Contact

About Evan Wong

Evan Wong is Co-Founder and CEO of Checkbox AI. A serial entrepreneur who founded Hero Education at age 17, Evan has built Checkbox from a bootstrapped Sydney startup into a legal AI platform serving 100+ organizations including Fortune 500 companies. Named to Forbes 30 Under 30 in 2019, Evan recently closed a $23 million Series A at a $100 million valuation.

About Fintech Chatter

Fintech Chatter is Australia’s leading fintech podcast with 350+ episodes reaching 30,000+ fintech professionals in 40 countries monthly. Hosted by Dexter Cousins, the show features conversations with fintech CEOs and founders about how they’re building category-defining companies.

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Full transcript.

Lightly edited for readability — filler words removed, wording otherwise unchanged.

Dexter Cousins
Fintech Chatter, the conversations fintech leaders actually listen to, presented by Tier One People, executive search for fintech.

Today I’m joined by Evan Wong, co-founder and CEO of Checkbox AI. Evan just closed a 23 million Series A led by Touring Capital. Checkbox serves over 100 organisations, including SAP, PepsiCo, Telstra, Woolworths, Macquarie Group and Hitachi, and they’ve been named in Gartner’s 2025 Hype Cycle for Legal Tech. Evan and I first met in 2017, when Checkbox won RegTech of the Year, and I’ve watched the entire journey unfold. Evan, mate, congratulations, and welcome back to Fintech Chatter.

Evan Wong
Oh, Dexter, thank you. It’s a pleasure to be here, and congratulations on 10 years.

Dexter Cousins
Yeah, we’re not quite there. I think it’s going to be in June this year, the official celebration. But I’m sure you went through exactly the same experience. You look at a blank laptop and go, what do I do now?

Evan Wong
Well, 10 years, well, almost 10 years on, both you and I are still here. And that says something, mate.

Dexter Cousins
That is something. And look, one of the themes that we’re running with the podcast this year is those enduring businesses. And this is why I wanted to get you on: not just to celebrate the Series A raise, but to talk about what it takes to get to that point, and the 10 years of blood, sweat and tears to become the 10-year overnight success.

Evan Wong
That’s right.

Dexter Cousins
So before we go through that, if you want to share with the listeners and the viewers a little bit about Checkbox and what you do.

Evan Wong
Yeah, absolutely. So Checkbox is an AI legal front door. We work with enterprise legal teams to help them better receive requests from the business, triage, automate and report on everything that comes into legal. So when you think about any of the customers that you’ve listed, let’s just say it’s Telstra for a moment, right? Telstra has their legal team in-house, but they also have their sales team, their marketing team, their regulatory compliance team. There’s many, many different teams that actually come to legal for help. We are effectively that front door for how people come to legal, and then how legal actually manages and sorts that work out. Kind of like Zendesk for legal, or Jira for legal, if you will.

Dexter Cousins
Yeah, awesome. So, as I mentioned in the intro, there’s some pretty impressive customers there. Walk me through what one of those customers might look like and how you’ve gone in and helped them.

Evan Wong
Yeah. So we tend to work with larger companies, and that’s both in Australia but also globally. We work with a lot of the Fortune 500 as well.

Dexter Cousins
And look, the reason I ask this is, there’s a lot of complexity to work with these businesses. Hence why I’m keen to dig down a little bit deeper with that.

Evan Wong
Yeah. And that’s exactly why we tend to work with the larger companies, because there is that inherent complexity that happens when you hit a certain scale of organisation. The way that I think about it… I don’t know if you’ve seen this diagram before, Dex. You’ve got how communication gets increasingly complex with more people that you add. It’s like a node; two nodes, you draw a line between them, they just communicate with each other. You’ve got three nodes, there’s a triangle. Four nodes, it’s a square with an X in it. And as you add more and more nodes, it becomes this sort of 5D where the complexity just exponentially scales. And that’s exactly what happens in larger companies, where you have a legal team of, let’s say, even 20, 50. Some of our customers have legal teams in the hundreds. When you have that size of a legal team working with tens of thousands of employees, the ability to efficiently come to legal for the concerns that you have just becomes impossible without a system.

And so what our customers do before coming to Checkbox is working out of email, Teams messages, spreadsheets, if they’re as advanced as using a spreadsheet to track their stuff. But it’s all siloed data. There’s no automation, and there’s no sense of prioritisation. It’s just drinking from the fire hose, like a queue of legal work coming in. And so what we’ve done is we’ve helped build AI agents that live in these native business mediums like Slack, Teams, email and even Salesforce. And we basically auto-categorise the requests that are coming into legal, and then we might solve it with self-service, or the AI might answer questions. It kicks off workflows, and it might create tickets, effectively, what lawyers call matters, so that the lawyers can actually work on just the most important, interesting work.

Dexter Cousins
Cool. So that help desk notion that you mentioned, it’s almost like bringing startup workflows into the legal world.

Evan Wong
Yeah, it’s a tried and tested model. It works in all these other functions. IT has their version of it with their ITSM. Support teams have it with their support management systems. Even HR has their own system of record in tools like Workday, et cetera, right? But legal somehow has gotten this far without having that version of software, that foundational operating system. So that’s what we’re building.

Dexter Cousins
Got you. So when we first met, the focus of the business was very much on no-code building. You mentioned the AI agents, which take that no code to the next level. And I always remember you first pitching Checkbox AI to me, and the thing around no code was, and I’ve benefited from it myself, whether it’s building a website or whatever, is that I still struggle to see a lawyer getting into even no-code tools. I was pretty fortunate: I was a graphic designer before I was in recruitment, and so whilst I hadn’t used maybe web tools, I’d used stuff like Photoshop and layout tools and click and drop and WYSIWYG, and so I was familiar with all of those ways of working. How have you found now the evolution of AI agents in helping you build out the proposition?

Evan Wong
Yeah. Well, first of all, we love no code. We’re still a no-code product. We haven’t changed from that. And our customers still love it; we still differentiate in the market.

Dexter Cousins
Talk about Claude, right, and what they’ve just released. It’s no code, right? I mean, it’s incredible, right?

Evan Wong
It’s quite funny: the same concept still exists, it’s just taken a different form. No code, back when we were building it way back many years ago, was in the form of drag and drop. It’s like, okay, let’s take coding into a visual medium. And we had a lot of success with that, and our customers still do that today, and surprisingly, lawyers actually do use our no-code product to do exactly that. But no code has also taken a new form today. I think in the latest form it’s called vibe coding, if you will, right? But it’s effectively still automation, building software, creating digital assets without having to write hard code.

But for us, the world has moved, and so have we. We now have AI as being very, very core to our product. We have AI agents that solve very specific workflows. And we found a way to really thread the no-code workflow product that we started as together with this sort of agentic way of solving this, and it’s almost like the AI is now a new user experience layer on top of the workflows. So whilst you may build the workflows, rather than the old way of having to fill out forms as a human, very forms-heavy experiences, how do we now use agents to turn that into conversation? But not just have that as a separate standalone chat tool. That was more the trend maybe two years ago, in 2024, 2023. Rather, how do you actually embed that experience into existing enterprise tools?

I think that’s actually where a lot of the opportunity lies when you think about GPT wrappers and these tools that are coming out. Or even Claude, about two days ago, I think, announced that they’ve launched their own legal add-on, right? It sent all the SaaS market’s stocks downwards. People always freak out when the foundation models move into the application layer. It’s like, oh, they’re going to come for us. But where you get a lot of the value in B2B enterprise application of these LLMs is really how well you can be embedded within the enterprise workflow, the enterprise systems, and being cross-functional in the way that it’s applied, rather than just a point system. And that’s why even what we’re building at Checkbox is really threading the workflow concept with that AI agent concept.

Dexter Cousins
Got you. And I was going to ask as well: obviously Harvey raised, I think, at a five bill valuation, EvenUp as a unicorn business. So there’s a lot of money that’s flown into legal AI right now. So how do you think and how do you feel about operating, and having raised now, alongside those kinds of expectations of valuations? You’re competing against people who’ve raised hundreds of millions, and now all of a sudden, as you mentioned, Claude released something and their valuations tumble. How are you managing through that?

Evan Wong
First of all, I think it’s actually a really good signal. I’m very happy that there are companies out there raising with such vigour, and investor sentiment is so high. It really, truly…

Dexter Cousins
Mate, and I’m with you, right? Media kind of reports the exact opposite of what is actually going on.

Evan Wong
Yeah. It’s one of those situations where all the boats rise with a higher tide. Butchering that phrase, but it’s good to see that. I think from a competitive landscape perspective, we’re all going to be indirectly or even directly competing for attention, budget. But there are so many problems to solve within the legal space, which is why there are so many companies, both incumbents as well as emerging, that are building in the legal AI space. It is just one of those industries that has been so underserved for so long, and has so much inefficiency in its service model, that there’s billions of dollars in productivity to be unlocked.

And the reason why it’s taken them so long, you can’t truly blame the industry for being laggards, because the technology just didn’t offer the user experience that was required for something as relationship-driven and complex as legal to adopt. But that changed with AI, because with Gen AI, all of a sudden you can dramatically improve time to value, dramatically reduce the friction of use of the user experience. And also there’s this reasoning and judgment that AI can do that really bodes quite well with legal analysis and work. So I think the time is now. I’m glad there’s a lot of money going into the space. It’s a great sign for anyone building in this space, but there’s a lot to build for.

Dexter Cousins
I think one of the other things as well is, you look at legal, you look at financial services, that’s heavily regulated. Legal, you’re always under scrutiny. One error, if you’re a legal firm, can bring you down; if you’re a business, it can bring you down. And hence I think there’s a way higher degree of scepticism in any technology evolution for these businesses. They’re always going to be the last adopters, because they’re going to want to triple check, quadruple check that it’s not going to get them into trouble.

Evan Wong
Yeah. Well, there is something of that. I think once you’ve got a really big organisation that you’re managing, you’re probably juggling between protecting the farm that you’ve built versus growing more crops, if you will. So I think it’s sensible, and it just means that if you’re building in this space, and particularly for enterprise and legal, you just have to take that into your product design and consideration and the maturity of your business.

Dexter Cousins
Yeah. I remember having somebody on the podcast last year, and they’re building a banking solution, and they said the conversation that they keep having with banking CEOs is, hey, we’re in a race to be number five, your number five customer, right? We want to see how the other four go beforehand. I think the challenge for anybody who’s building a tech solution, particularly for your business, where you do have enterprise customers, is limited time, because of capital. You can’t spend 18 months building a POC for a Telstra or whoever else; you have to move fast. How have you guys been able to win so many enterprise clients and keep the lights on? Because it’s 10 years now, and you’ve got to the point where you’ve raised a 23 million Series A. So it’s not like you’ve raised a lot of funding to actually get to this 10-year point. So how have you managed to navigate that?

Evan Wong
Yeah, I mean, the 23 million is not even capital we’ve deployed. It’s just capital we’ve just raised. And so we’ve raised up till this point, I think, a total of about 6 million. I’m measuring everything in USD, by the way. So 23 is USD, and so is the six.

Dexter Cousins
Let’s say 10 million Aussie dollars over 10 years.

Evan Wong
Yeah, exactly. It’s not a lot for the size of business we’ve grown to. We do eight figures now in annual recurring revenue, right? So pretty efficient in terms of amount raised to revenue growth achieved. A few things. I think this is what Australian companies are really good at: building with a very frugal mindset, and we build very efficient businesses. I mean, coming to the US and meeting with investors here, they’re always really impressed with just how efficient we are. And that’s something to be proud of, and I think we build high-quality businesses for that reason.

But in terms of winning large companies quick enough, I think you just get better at that over time, because your products mature, you’ve just had enough at-bats at this, and it’s like, oh, it’s the same pattern. We know exactly the process. We know this takes this long. And you come up with little tactics to compress the sales cycle. Our average sales cycle today is around three months, and that’s for companies like the Fortune 500 that are handing us six-figure USD deals, right? And so we’ve been really good at compressing the sales cycle for these large companies.

Dexter Cousins
So I remember the first time we did this, I didn’t even have a podcast. I had a blog, and I came to your office and recorded it and then transcribed it. And I mean, it took me, what, like two years to figure out, why do I transcribe it? Just put the thing on and let people hear it for themselves. But there was something that really struck me, and I still remember this like it was yesterday. We talked through the process of how you were getting customers. And it’s something I saw David Brear put out about 11:FS and their podcast, a thousand episodes now, and the recurring theme of every single one is every successful business has built with their customers, built with their customers in mind, talked to their customers. And I remember your approach, correct me if I’m wrong, but it was something along the lines of: you would reach out to people who were decision makers, who had the problem that you thought you could solve, in these organisations like Telstra, and said, hey, we’re building this, we think we might have the right idea, but we really need to hear from the end user. Would you be willing to have a look at it and let us know what you think? And that kind of approach.

Evan Wong
Yeah. Yeah.

Dexter Cousins
And it was like, yeah, sure. And I remember you would have been, what, like 23, 24 at the time?

Evan Wong
I think, yeah.

Dexter Cousins
Like, wow, this is awesome. And then getting in and getting the meeting, and not messing around starting at the bottom, having to spend 12, 18 months doing this dance, and people having their ego fest, or never really getting to talk to decision makers, or getting to talk to one person when there’s five decision makers. Are you still following that process now, to an extent, and building with your customers?

Evan Wong
That never changes. I think any company that stops doing that will lose, because ultimately that’s why you exist. It’s to serve your customers, and whatever their needs are today are not necessarily the needs tomorrow. Especially in today’s world, where the business environment is moving so quickly. You and I were just talking about this right before we went on air, right? The business world is just… things are moving quicker. AI is applying pressure. It’s just a bit hectic. And so when the market and the business world is so dynamic, your understanding of the market, your competitors, your customers, it changes day by day, and you have to keep a finger on the pulse, and you have to be building constantly towards finding PMF, product-market fit.

People think, and this is me too, I actually thought the same, I’ve learned so many lessons in these last nine years, people think that achieving product-market fit is a moment in time. You achieve it, you’re there, you’re good. But it’s not true, because there’s a key word in product-market fit, and the word is market, and the market changes all the time, which means it’s dynamic. So you can have PMF in a moment of time, and then you have to constantly chase it in order for you to maintain it as well. So yes, that’s what we still do today. We are very close to our customers, and we build very closely with them.

Dexter Cousins
One of the challenges that I’ve noticed, and it’s been reflected in a lot of the briefs that I’ve worked on, probably for the last two or three years now: it’s predominantly been SaaS businesses who have started off with a product. They then get success, they get investment. There’s then more pressure to go and obviously scale the business, and scale usually means go to the US and/or build more products. And what they tend to fall into, Evan, is this trap of: they start building products based on customer complaints, not on what the customer really needs. And then there’s another added complexity, in that usually most businesses start off not enterprise, but go after the easy wins. Enterprise is a really hard win. And they then start to get enterprise clients as they get momentum. But that then totally changes their model: their sales model, their operations model, product. And what tends to happen then is this recognition that, we always thought we were a product-led business, but we’re not, we’re sales-led. They then have to bring everything, almost like product being the central hub, the engine room of the business, and then everything else, technology, sales, marketing, operations, everything has to revolve around that central node of product. And it then becomes almost like an enterprise-style transformation for a business that’s meant to be scaling. What have you noticed about that journey? You obviously had enterprise clients from day one. Have you been able to bypass that and skip it?

Evan Wong
So you’re right, we never went through that trend that most SaaS companies go through, because we started at the top end of town. We started with enterprise. So I know a lot of founder friends who built really great mid-market businesses and want to move into enterprise, because it’s stickier, it’s bigger contract values, you can add growth much more quickly. But then they struggle, because their entire product, their DNA, their go-to-market motion, is all built on this mid-market approach. It’s really hard to go up. It’s funny, because it’s easier to start mid-market and move up and deal with the pain later. We dealt with the pain up front. So we had to do SOC 2 early. We had to build really robust features for enterprise at the get-go.

But I think one of the things you mentioned there is having your roadmap completely derailed or determined by your enterprise customers. And that was definitely something that we were very conscious about at the beginning, when we had very few customers, very few data points, but they were very big customers that wanted certain things. And this comes down to really good product design and product management, which is always taking everything from a customer as a data point, but not as an instruction and not as gospel. You have to take it as a data point, and then you have to ask yourself questions around what is the broader market view of this. This might be really important to this one customer, but is it important to 500 other customers, 10,000 other customers? And then having your own viewpoint as well.

Customers often explain what they want in solution form, but they’re not actually the solution experts. As a software company, you’re the solution expert. The customer is the expert in the problem. And so what you don’t want to do is ask your customer for solutions. You want to ask them for problems. Why do you suggest that feature? Why do you suggest that we need to build this? And you understand the problem. And that’s really where you get the foundational, universal understanding, and then you should design the right feature to solve it in the best way, as a product company.

Dexter Cousins
A mentor of mine once said to me, a camel is a racehorse designed by committee. And I think it perfectly summarises the trap that you can fall into when you want to please customers so much that you listen to them. And I think without that rigour and discipline around collecting the data and then analysing it and then going, hey, where’s the commercial opportunity here… You see so many businesses… we’ve got terms for it, like the valley of death, right? And it’s usually those businesses that are trying to get from mid-market to enterprise that fall into it, and they end up being nothing to nobody, because they’ve ended up designing a camel rather than the racehorse.

Evan Wong
Oh, yeah. And the dangerous thing about transitioning that segment is, when you start to build for enterprise, that’s inevitably going to add more drag onto the product that your mid-market customers don’t actually need. And to your point, you’re trying to be everything to everyone, and so you end up being nothing to any particular group. That’s another big thing I’ve learned in these years: being very clear on segmentation, your ICP, your ideal customer profile, and deciding who are not your customers. Who are not your customers is just as important as who are your customers, because that gives you clarity in who you want to build for, and the kinds of cycles you want to even spend your time on as an executive, or your sales team’s time, and right through to the rest of the business.

Dexter Cousins
So a lot of my founder network, particularly in this last 12 months, as I’ve been having conversations with them, whether it’s been dinner, drinks or whatever, they’ve confided in me something along the lines of: if I was starting the business now, instead of back in 2016, I would do things so differently. And I think there’s a general consensus… there might be some variation on the number, but most of them are of the belief that, hey, I could build a billion dollars of revenue with like 30, 50 people. And I truly believe that as well, right? I think now the technology is at the point where, if you get the right people in, you can build something… we’ve never had more power at our fingertips. Where are you at now in terms of the size of your team? And you touched on this earlier, about the differences between Aussie startups and the US, and how we’re a lot more efficient. What’s your vision for the business from a people perspective, and how big you can get revenue-wise, but how are you going to actually get there in terms of building a thousand-person organisation? What’s the thinking around that?

Evan Wong
Yeah. So we’re a 75-ish person business at this point, but we’re scaling, so we’ll be at about 100 next quarter. In terms of how we think about people and how far you can scale, I think it would be silly to build under the traditional model of expecting a lot of people to support a growing business. I think every business leader has been thinking about, or has been advised by their board or by consultants, to leverage AI today to scale much, much further, because it is possible. There’s actually great case studies. There’s companies out there like Cursor who have gone to really, really big scales of revenue with a very, very lean team. So you’re absolutely right, the tools are there now. It’s kind of like what the internet did many years ago for creating a business. Starting a business was much harder pre-internet, and when that happened, that lowered the bar, if you will. And AI is doing the same, the next generational shift. So for us, we’re scaling, but we are telling every single person in our company to be leveraging AI wherever they can. And with roles that we’re hiring for now, AI proficiency, an AI-first mindset, the ability to think about resource allocation with AI in mind, becomes really important, particularly for leadership.

Dexter Cousins
Yeah. What does AI first look like to you? Because, we talked about this before we started recording, certainly my observation is I’m seeing a rapidly increasing disconnect between what an employer’s expectations are and what an employee thinks is expected of them. How do you define AI native, an AI-first mindset, and what does it look like in terms of a set of behaviours and experiences that you’re looking for when you hire people?

Evan Wong
Yeah, it is a mindset. So it permeates across multiple things. I’ll give you some examples. Do you first jump to hire someone when you need more bandwidth, or do you first consider what sort of AI tools you can use to get more bandwidth? Which order of operation happens in your brain? It’s okay to still hire a human, right? But is your first thought to jump to that, or is it to think about, can we get some leverage with technology? Another example would be in the hiring: how much inherent curiosity and experimentation and hands-on experience have you already had with AI? This doesn’t have to be in the context of work, though obviously that’d be nice, because it’s better aligned in an interview context. But it’s also, are you just natively using AI in your day-to-day, whether it’s creating images or videos, or how you use ChatGPT? Because all of this teaches you what AI can do and what it can’t, and it teaches you, just through practice, best practices when it comes to prompting and working with AI tools. So it’s a level of curiosity, it’s a level of hands-on experience. I think there’s always the ability to talk at a high level about AI, but are you really in the tools themselves? And there’s so many free tools today that you can just use to get acquainted with AI. That’s what I mean by AI first: it’s having that proficiency, but also the curiosity and the mindset to solve things with AI.

Dexter Cousins
Yeah. And look, I think it ties in really to the qualities that have always been required to be successful in an organisation like yours, right? Ultimately, the wrapper that we might have been using back then, when we first met, was growth mindset, right? It’s just this hunger to learn.

Evan Wong
I think the world is going to keep spinning, and technology is going to keep moving forward, and as a single person you’re not going to be able to stop that. And so if you’re not the one that’s acquiring the skills to understand the future… and if you feel like your role and your skill set is under existential threat, that is even more the reason to be the person that actually gets ahead of that, because then you acquire and you evolve into the next level of talent. It’s a technological cycle. You look at when people said, hey, you’re not allowed to use calculators. And people would say, oh, well, you shouldn’t use calculators, because you won’t have one on you all the time. Well, that’s changed. You’ve got a calculator on your phone all the time; it’s always going to be available on your computer. And the same thing happened even as you transitioned from the typewriter to the internet. And again, AI is going to be that next wave, where it really is a tool. And yes, there’ll be a lot of old skills that will be challenged, but there’ll be a whole bunch of new skills and professions that’ll be created as well. It’s just the nature of, I think, human evolution. There will never be a shortage of…

Dexter Cousins
And you think of the narrative, right? Every narrative about AI is you’re powerless, whereas we’ve never had a greater opportunity in the history of humanity, right? People talk about how funding’s unfair, and I say, well, it is, right? But the reality is you don’t need funding now. If you’ve got an idea, you can go and build it and have a prototype up within a weekend. If it’s that great, you’ll be able to make money from it, and you won’t need to get investors, right? Let your customers decide whether you validate your idea or not. And I think that level of power is just being totally pushed aside, and it’s creating this victim mentality, this fearmongering that we’re all going to be slaves, and every single AI reference is Terminator, Blade Runner with replicants. None of it’s actually about the great stuff that’s happening.

Evan Wong
Yeah. Well, I think fear sells, and it travels further. And it’s valid. I’m not saying that it’s a one-sided coin. I think it’s a two-sided coin, like most things in life. Again, tools can be used for… I mean, it’s probably not as dichotomous as good and evil, but there’s always going to be different applications of tools.

Dexter Cousins
Yeah. Look, I mean, that’s the reality with technology, right? The irony, or the paradox, is that the innovation has been done through illegal means and organised crime, right? And that’s the reality, whether it’s crypto, whether it’s AI for fraud, the internet for porn. These were all the drivers of the innovation that we benefit from today for much more positive, practical uses. And I think that’s just a reality that you have to accept as humans, right? We’re flawed, right? We’ve gone totally off on a tangent.

But look, Checkbox isn’t your first rodeo. You had a start at the tender age of 17, which you successfully exited. Now you’ve got, what is it, 15 years of experience under your belt as an entrepreneur?

Evan Wong
Yeah, something like that.

Dexter Cousins
What’s your advice to… let’s say my 14-year-old daughter’s listening, what would be your advice to younger people? And what would be your advice to people like me, who 10 years ago decided to take the plunge?

Evan Wong
When you go out and you start your own thing and you build something, it is a lot of hard work, and so you have to be unafraid of that. There’s going to be a lot of adversity, things that go wrong all the time, so you have to be ready for that. And so there’s a level, I think, of even privilege, if you will. I’m not going to sit here and say, oh, everyone should go and start their own thing, because I think that would be bad advice. I think you have to understand that I’ve had the privilege to have a safe enough environment to go and do my own thing, to take risk. But if you’re as lucky as I was in being able to take some risk, then I would say go for it, especially if you’re young.

Because when you’re young, and this was my mentality, by the way, Dexter… People used to always ask me, a few years ago, Evan, how did you have the courage to go and just start your own thing, instead of going and finding a job like every one of your peers? I never really worked in corporate. I’ve done a total of four weeks in my entire life working for a big company; that was an internship at KPMG when I was still in uni. And people ask me, how did you just have the courage to do that? And I said, well, actually, to me it’s the opposite, which is: when we’re this young, you can take outsized risks and life will be okay. You start a business, it fails. Even if you spend two years on it, who cares? Now you’re, what, 20 years old, if you started at 18, right? You’ve got the rest of your life. You basically haven’t fallen behind. If anything, you’ve gotten ahead, because of all the lessons that you would have learned that uniquely come with trying to build something from zero to one.

So I think if you have the privilege to start something when you’re young… I’m a big proponent of it, if you have a passion behind it. Again, it’s one of those things where you don’t want to just start a company because someone told you to on a podcast. You have to have a passion for it. But if you have an itch, you have an inkling that you want to start something, and you’re young, it’s a no-brainer for me. The risk profile is super… you don’t have a mortgage, you don’t have kids to support. Go for it.

Dexter Cousins
Maybe I should do the advice bit for the older person then, because I’ve actually done it, right? And it’s actually the opposite of…

Evan Wong
Please tell me what you said. I would love to hear.

Dexter Cousins
I’ve got a load of little things that I read every morning, right? Beliefs and values and stuff like that. And one of my beliefs is: it’s much better to feel fear than shame, right? And I’d got to a point in life where I had everything to lose by doing this. And so there was a fear there, to not do it, but that was overridden by the shame of me getting to the end of my days and not doing it, and what kind of person would I be? And it ties into your passion thing, right? Mine was, I’d always dreamed of having my own business. And it had got to the point where the fear’s there and the shame was there, and that was the tipping point where I was like, I’ve just got to do this, right? And it was a big risk, and we could have lost everything, and thankfully we didn’t. And thankfully, to everybody that’s out there listening, and the support that I’ve had over the years, we managed to make things work.

And it’s kind of funny, I was just saying to somebody yesterday: had you told me 10 years ago this is where you’d be, I would have snapped your hand off. But sitting here right now, I’m not satisfied at all, right? I want more. So that shame thing is almost like the driver, right? And I think you’ve got to be careful with it, because it can only get you to a certain point, and then you have to find some other form of energy to get you to that next level. Which, look, I think you’re probably going to get to as you get older and the business gets bigger. It’s like, okay, right, what’s the next thing that’s going to drive you? And I think the trap is, it can be really powerful having anger or fear as an initial force, a driver, but you get exhausted after a couple of years, particularly if you’ve got your own business, and it starts to become counterproductive. And I found that a couple of years in, I had to find energy from different things, and fortunately I managed to do that.

Evan Wong
Yeah, good on you. I think it has to come from a place that’s deep within. Again, people always say, I want to start my own business. If you’re doing it for vanity, forget it, man, right? Vanity, get-rich-quick scheme, I don’t want to work a nine to five, I don’t want to have a boss. All these reasons are terrible reasons, because actually starting your own business is almost the inverse of all of those. You’ll work more than a nine to five. You’ll have multiple bosses, which is your employees, your customers, your investors. It’s definitely the harder path, but I wouldn’t do anything different. I am in love with company building, and that’s what you need to be. You need to be obsessed and deeply in love with the journey and the process and the building. Because I haven’t woken up a single day of these nine, 10 years, Dex, where I haven’t leapt out of bed ready to build, and I haven’t gone to bed wishing there were more hours in the day to build. I love building.

Dexter Cousins
Yeah. And look, I think that’s kind of the secret, right? It’s like, this stuff gives you energy.

Evan Wong
Yeah, absolutely. I think every person and every company’s journey is going to be… it’s not really that you’re running your own race, because there’s a lot of competitive pressures, particularly in software, but every company’s journey is unique. And I’ll give you a good example. Notion, funnily enough, had a very similar origin mission as Checkbox. They had this sort of no code, let people build software across the enterprise, but they went more into the documents and collaboration space; we went into the workflow space. But they also took, I think, six years before they started… they were plodding along for six years before they started to take off. And some companies start and a month later they’re shooting off, right? And some companies take a long time. Nvidia, by the way, took more than a decade. It’s always a meeting of the right product and the right timing in the market. And building a company is kind of like you’re on a surfboard on the ocean and you’re waiting for the waves. You basically just have to wait for the right wave to catch, but you don’t want to fall over and drown before that wave comes along. So yeah.

Dexter Cousins
If we all had 100 years, every one of us would be successful, right? But the problem is, in the world that you’re in, the world that I’m in, you don’t get 100 years. You don’t get 100 days, right? It’s literally working 100 days out, earning the right to the next 100 days, earning the right to the next 100 days, right? And it’s really hard to build something when you’re in that. Just ask any person: if they’re constantly in stress mode and survival mode, you can’t lose weight, you can’t get fit. Your body is just racked with hormones, right? So it’s impossible for you to be healthy if you’re always in that mode. And the same is true of organisations. And obviously when you get to the point where you raise 23 million, the stress, the cortisol, is going to drop, right? You can then go, okay, right, let’s start to get a healthy organisation, start to fix all of those things.

And it’s really interesting with that analogy, Evan. If I look at the experiences that I’ve had of helping businesses at this stage, there are so many who have just had to earn the right, earn the right, earn the right. And then you get to the point where you’re 50, 75, 100 people, you’ve got the money now, you do want to scale, and you lift up the lid and you go, ah, look at the mess, right? Culture is toxic, systems are all over the place, tech stack’s crap, you can’t scale it. And you get set back, and all of that money that you’ve raised goes on to fixing the problems that you’re now encountering, when really the expectation from your investors is, hey, where’s the growth? It’s like, oh, we’ve got the business on life support, because it’s been in this state the whole time. So it’s fantastic to hear that, on the journey that you’ve been on, all of those problems have already been addressed, so that now you’re at the point where those investment dollars can be utilised truly to help you scale and grow the business, not just to get it into a functioning state so you can then go and scale and grow the business.

Evan Wong
Yeah, I think in today’s climate, I would say it’s pretty hard to raise money if you’re in that life support mode anyway. Savvy investors are looking at trends. They’re looking into the trends of your business, I should say, and they invest at inflection points. So we’re quite grateful. We’ve built a very high-quality business with great efficiency metrics, and now very interesting growth rates as well. And we are very excited about putting dollars behind the organisation, because, exactly to your point, it’s not used to fix a leaky bucket. It’s really building forward.

Dexter Cousins
Got you. And what are the plans for the next 12, 18 months?

Evan Wong
In terms of scaling and investment, we have really two buckets. One is a lot of investment in our EPD team, so engineering, product, design. That all still basically comes out of APAC, with a very strong hub in Sydney, Australia, where our office is still based. So a lot of designers, product managers, engineers. This is an AI race. We’re competing on the global scale here in the US. And when you think about these foundational models moving into the application layer, like we just talked about with Anthropic, you have to earn the right to be an application layer well above and beyond these AI model providers. And so there is a speed of execution, there is a quality of execution, that needs to be in place, and so a lot of it is going into the product.

The other one is go-to-market. That’s a given. We have found product-market fit. People at scale really want to buy what we have, and so now it’s just a matter of helping them find us, and us find them, and then beating out the competition. So those will be the two big areas. But we really want to become the cornerstone technology for enterprise legal teams. In the same way that you would never start a sales team without Salesforce or HubSpot as your CRM, you shouldn’t start a legal team without Checkbox. And so we’re really building towards that vision, and that’s a pretty big vision to fulfil, and so that’s what we want to do in the next two to three years.

Dexter Cousins
Awesome. Well, mate, it’s been fantastic to have you on. Congrats to you and the whole team. We get some awesome talent listening to this show. If anybody’s interested in finding out more about how they could become part of the Checkbox journey at this really exciting inflection point of the business, what’s the best way for them to find out about careers?

Evan Wong
Yeah, go to checkbox.ai/careers and you will find all of the roles that we have open, and you’ll be able to contact us that way.

Dexter Cousins
Awesome. Evan, thanks so much for joining me. Mate, it’s been really heartwarming, this chat, obviously seeing the journey that you’ve been on. And I guess it’s a real inspiration for others: the light at the end of the tunnel for many has been a train coming full speed at them, and to know that the light at the end of the tunnel actually is the light at the end of the tunnel, I think is a great story to end on.

Evan Wong
Absolutely. Grit, resilience, perseverance. It pays off.

Dexter Cousins
Awesome. All right, mate.

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