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.
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.
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."
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.
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.
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."
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."
"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."
"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."
"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."
"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."
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."
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.
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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.
Watch the full conversation:YouTube link
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