How Checkbox funded global growth without giving away the company

For enterprise businesses, digital transformation has gone from a nice-to-have to a top priority — and for good reason. Automating manual processes can save large companies millions in operating costs, and it can sharpen the customer experience that so often separates market leaders from everyone else. The hard part has always been the build: traditional software development is slow, expensive, and gated behind IT.

Checkbox set out to change that. Founded in 2016 in Sydney by Evan Wong and James Han, Checkbox is a no-code automation platform that puts software creation in the hands of the people who actually do the work. Legal, HR, risk, compliance, and procurement teams can build and deploy their own workflow apps — with a simple drag-and-drop interface, no code, and no waiting on IT. What once took months takes days.

The team built the business with discipline and capital efficiency, raising funding strategically rather than constantly — and the approach worked. 

Within a few years of launch, Checkbox had won over some of the largest enterprises in the world, its customer list boasting Forbes Global 2000 companies including Allianz, Telstra, Woolworths, PwC, and Coca-Cola Europacific Partners, and earned recognition as a Market Leader in No-Code Automation by Gartner Digital Markets.

How did they turn that early momentum into a $100 million valuation?

More runway, less dilution

By 2022, Checkbox had a clear window in front of it. Enterprise demand for digital transformation was surging, and the company had a genuinely differentiated, globally applicable product in a fast-growing category. The opportunity was to expand aggressively — into the US, Singapore, and Malaysia — while the market was wide open.

That kind of expansion takes capital. Checkbox had just closed a $4.5M USD pre-Series A equity raise led by Sequoia India's Surge and Australia's Tidal Ventures, giving it real firepower. But funding an ambitious global push on equity alone comes with a familiar tension: burn through a fresh round too quickly and you're back to fundraising, diluting founders and team again — often before the business has fully capitalized on the very momentum the money was meant to fuel.

Wong and his team wanted to make that early equity raise go further. 

A modular approach to capital 

Checkbox constructed its own capital stack using both debt and equity. The modular approach gave founders maximum flexibility to scale the business and maintain capital efficiency on their terms.

Following its pre-Series A round, Checkbox raised $1M AUD in non-dilutive debt financing from Lighter Capital. The debt complemented the equity: it extended runway, funded continued investment in go-to-market and product, and let the team keep scaling — all without additional dilution at a stage when ownership heavily influenced outcomes.

It's a hybrid funding model more and more high-growth SaaS founders have embraced. Using debt and equity together, a startup can move fast, preserve valuable ownership, and deploy the right capital exactly where and when it counts.

That fiscal discipline compounds. Every dollar raised as debt rather than equity is a dollar of ownership the founders and team hold onto — and as the business grows and its valuation climbs, that retained equity can become life-changing money. Non-dilutive debt isn't just cheaper, faster money; it's how founders build enterprise value while keeping more of it.

The payoff: a $100M-valuation Series A 

The strategy paid off. On the strength of its combined capital stack, Checkbox accelerated its global expansion, opening up the US, Singapore, and Malaysia and winning new multinational customers including Danone, Telefónica, SITA, and Glencore. It shipped meaningful product innovation, too — an in-product workflow template library and integration connectors with core enterprise systems like Salesforce and SharePoint — while co-founder and CEO Evan Wong was named LegalTech CEO of the Year.

From there, Checkbox kept sharpening its focus. The company doubled down where its no-code automation delivered the most value — enterprise legal teams — evolving into what Wong calls "the AI Legal Front Door for in-house teams." Rather than leaving legal work stuck in siloed inboxes, Checkbox drives routing, automation, and visibility across everything a legal team handles. 

The impact has been striking: customers report cutting the volume of low-value, repetitive legal requests by 50–80% and improving turnaround times by as much as 85% — freeing lawyers at companies like SAP, Hitachi, and PepsiCo to spend more time on meaningful work.

That focus attracted serious backing. In January 2026, Checkbox raised a $23M USD Series A led by Touring Capital at a reported $100M USD valuation, with participation from Peak XV Partners (formerly Sequoia India), Conductive Ventures, Tidal Ventures, Five V Capital, and Workday's Head of Agentic AI, Jerry Ting. 

Today the platform is used by more than 100 enterprise organizations, including Telstra, Woolworths, Coca-Cola Europacific Partners, Xero, Hitachi, and PepsiCo. For Wong, the recent raise is driving the mission rather than a change of course — funding, he says, that lets them "go further, investing in product, AI, and our team, so that legal teams can focus less on managing demand and more on the work that matters."

Wong is candid that the milestone came from years of deliberate capital execution and efficiency. By his own account on the Fintech Chatter podcast, Checkbox raised remarkably little before its Series A — even as it grew to eight figures in annual recurring revenue. 

"Australian companies are really good at building with a frugal mindset," Wong said, noting that US investors are consistently impressed by how efficient the team is. 

Where many startups either scale at all costs or run out of road, Checkbox sustained itself over a longer timeline by building lean and staying focused on enterprise customers — and by using non-dilutive debt to complement its equity at a pivotal moment, its founders reached a nine-figure valuation with more of the company still in their hands than a conventional venture path would have left them.

It's a trajectory built on momentum captured at exactly the right moment — and on a capital strategy that, from early on, treated equity and non-dilutive debt not as either/or, but as better together.