Evan
Wong

Evan Wong spends his days on a problem most people outside a corporate legal department never see. Every large company has a legal team, and every legal team is buried under the same repeating requests - review this contract, approve this vendor, sign off on this policy, answer this question that someone already asked last month. Wong's company, Checkbox, sells the software that catches all of it at the door.

He calls it the "legal front door." An employee sends a request through a form, a Slack message, or an email; Checkbox reads it, routes it, and where it can, handles the work automatically using AI and no-code workflows the legal team builds themselves by dragging and dropping. The pitch to a general counsel is simple - stop drowning in intake, and let your lawyers spend time on the matters that actually need a lawyer.

In early 2026, that pitch pulled in a US$23 million Series A led by Touring Capital, at a valuation reported around US$100 million. The round put a number on something Wong and his co-founder James Han had been building quietly for close to a decade. Checkbox now serves more than a hundred organizations, including names like PepsiCo, SAP, Telstra and Woolworths, and the company has moved its center of gravity from Sydney, where it started, to an office at 99 Wall Street in New York.

It started with a homework assignment

The origin of Checkbox is almost too neat. In his final year studying Commerce and Law at UNSW Sydney, Wong turned in a submission for a law course - an idea about making legal and compliance content more automated and personalized. That assignment became the seed. He was not new to starting things. At 17 he had launched an education company, Hero Education, and by his own account got "hooked" on the feeling of building. When he left university at 22, starting a company felt like the natural next step rather than the risky one.

His first real attempt was not Checkbox at all. It was a product called Comployment, aimed at helping small businesses keep up with employment compliance rules. It taught him an expensive lesson: small business owners would not pay to manage a risk they could not see. He pivoted. The insight that survived the pivot - that legal and compliance work could be turned into software - became the foundation of Checkbox in 2016.

Bootstrapped, then focused

Checkbox did not arrive fully formed. Wong and Han met in high school, studied together at UNSW, and bootstrapped the early years with no salaries. The first product was a general no-code automation platform - the promise was that a business person, not an engineer, could build working software by dragging boxes around a screen. Legal, HR, procurement and compliance teams all used it. That breadth was a strength in the pitch and a weakness in the roadmap.

The decision that shaped the company was narrowing it. Checkbox cut away the other industries and pointed everything at legal. Wong has been candid that focus felt like shrinking the opportunity when in fact it sharpened it. Paired with an enterprise-first strategy - building SOC 2 compliance and heavyweight features early rather than chasing smaller, easier customers - the narrowing is what let Checkbox win the blue-chip logos it now runs on.

How he runs it

Wong's operating philosophy has a couple of lines worth keeping. The first is about listening to customers without being led by them: "Take everything from a customer as a data point, not as an instruction." A request tells you where the pain is; it does not tell you what to build. The second is a question he uses in the AI era before adding people: "Do you first jump to hire someone when you need bandwidth, or do you consider what AI tools can give you leverage?" For a company whose entire product is about replacing repetitive work with automation, that is less a slogan than a house rule.

The recognition has followed the work. Wong was named to the Forbes 30 Under 30 Asia list in 2019 alongside Han, has spoken on a TEDx stage, and has been named LegalTech CEO of the Year. But talk to him and the trophies are not the story. The story is a decade of understanding one customer - the corporate legal team - better than anyone else was willing to.

What comes next

The Series A money is aimed at scale: more AI in the triage engine, more of the routine legal request pipeline handled without a human, and a deeper push into the US enterprise market that the New York move signals. At one customer, Hitachi, Checkbox says 83% of routine legal and compliance requests are now partially or fully automated. That figure is the whole thesis in miniature. If Wong is right, the "front door" becomes the default first stop for every legal request inside a large company - and the lawyers behind it get their time back.