From classmates to legal AI pioneers: The UNSW alumni founders behind Checkbox

We actually met long before university — in Year 7 of high school where we became close friends. By the time we both attended the University of New South Wales, we already knew how each other thought, worked, and handled pressure. But it was really at UNSW where that teenage friendship evolved into a professional partnership built on years of trust, shared ambition, and complementary strengths. We were exposed to new ideas, diverse disciplines, and an environment that encouraged big thinking. We were both active in UNSW’s rich student life and extracurriculars, including pitching start-up ideas together at leadership camps and the Peter Farrell Cup. That long history is something we don’t take for granted. It meant that when we eventually decided to start Checkbox, we weren’t just co-founders figuring each other out, but were partners able to dive head first with an incredible amount of understanding and trust in each other. – Evan Wong 

Our degrees shaped the way we approach problems but in very different ways. James studied Engineering, which deeply influenced how we think about systems, infrastructure, and scalability. Engineering trains you to break down complexity into structured components, identify bottlenecks, and design something that works not just today, but at scale. That systems mindset has been foundational to how Checkbox is architected both as a product and a company. I studied Law, which built effective communication, risk analysis, and structured problem solving, which are skills that make me an effective leader today. We both also did a double degree in Commerce which gave us a foundation in the language of business, understanding accounting, finance, marketing, markets, and economics. But the craziest fact that almost no one really knows about Checkbox is that the very first idea for the company came from a submission I made for one of the assessments in a law course I was taking in my final year at UNSW. It has evolved a lot since that initial idea though, of course. – Evan Wong 

We started with the belief that business users should be able to build software without writing code. But after speaking to customers, one pattern stood out: legal teams were overwhelmed by manual intake, scattered processes, and zero visibility into their workload. The turning point was realising that automation wasn’t the only thing legal needed — it also needed infrastructure. That’s when we shifted focus and began building what we now call the “legal front door” — a structured way to capture, triage, and manage all legal work for in-house teams. – James Han

The biggest shift was learning to act before feeling ready. We worked unpaid for over two years alongside early co-founder Paul Wenck, learning everything from product to sales to hiring. We became comfortable with uncertainty and focused on listening obsessively to customers. We’ve always believed the best founders are great learners — curious, open-minded, and willing to adapt quickly. – Evan Wong

Raising capital is a by-product of building a high-quality business. So the process started years ago and rather than focusing on raising money, we focused on building a great business with great metrics. Having said that, raising capital is also about conviction and future growth potential. Investors are betting on the size of the problem and the team’s ability to solve it. One of the biggest challenges fundraising was articulating why legal operations is a massive, underbuilt category — and why now, especially with AI, is an inflection point. - James Han

Our journey has been anything but linear. There were years of uncertainty, product pivots, tough conversations, and moments where progress felt invisible. People see the funding headline or valuation, but they don’t see years of sacrifice, the failed experiments, and long periods of things just not working. But we loved every moment of it. You have to love the game and you have to love the journey. It’s too difficult otherwise. – James Han

Relocating to New York two years ago was a defining moment. It signalled our commitment to building a truly global company and placed us closer to customers and investors. But more meaningful than any single milestone is actually seeing real life customers and users completely improve their quality of life at work, transform their careers, and make a meaningful impact in their businesses, because of Checkbox, something that was nothing but just an unproven idea in our heads a few years ago. – Evan Wong

History definitely helps as James and I have known each other since we were 12. But beyond that, it’s clarity of roles, mutual respect, and shared values. We also have complementary skill sets but with enough understanding in each other’s strengths to bridge empathy both ways. We challenge each other directly, but we’re aligned on the mission. When pressure rises, we come back to first principles: what’s best for the company? – Evan Wong

Legal has historically operated reactively. We’re building the infrastructure for legal operations that makes it proactive and data-driven. Checkbox centralises intake, triage, and reporting — and with AI, we’re enabling smarter routing, faster decision-making, and greater visibility, allowing legal teams to finally operate like other business functions — measured, strategic, and deeply integrated in the enterprise. Over the next five to ten years, lawyers will no longer start any piece of legal work from scratch. It is likely that they will not be the ones doing the legal work in the traditional sense that we understand it today. Instead, they will be managing and orchestrating teams of AI Agents that start, iterate, and complete legal work. The lawyer in this future focuses on relationships, real-world human interactions, and applies sharp judgment to review and quality control to maintain trust and governance in the delivery of AI-native legal services. – James Han

Honestly, there is no better time to start than now. The stakes are low. The ceiling is high. The worst thing that can happen is you fail and you walk away with learnings of a lifetime. You’re still young. The best way to learn how to build a startup is to go build one. What matters is curiosity, resilience, and an incredible and insatiable appetite for learning. – Evan Wong