Checkbox has raised a $23 million Series A round to accelerate development of its AI Legal Front Door platform, positioning the product as a single entry point for legal teams to capture, manage, and measure enterprise legal work. The round was led by Touring Capital, with participation from Peak XV (formerly Sequoia Capital India), Conductive Ventures, Tidal Ventures, Five V Capital, and angel investors including Jerry Ting, VP and Head of Agentic AI at Workday and former co founder and CEO of Evisort.
The company is targeting a long standing operational bottleneck inside legal departments: rising volumes of requests from the business that arrive through scattered channels, often via email threads and ad hoc messages, creating heavy triage work and limited visibility into demand. Checkbox says its platform centralizes intake from where employees already work, including email, Slack, Teams, Salesforce, and intranet portals, then uses AI agents to convert conversations into automated workflows for routine requests while routing complex or higher risk matters to the legal team for direct handling in the product.
Checkbox reports adoption across more than 100 enterprise organizations, including SAP and PepsiCo, and says customers use the platform to reduce administrative overhead and improve service delivery. The company highlighted a case at Hitachi in which 83% of routine legal and compliance requests are now partially or fully automated, allowing legal and compliance staff to focus on higher-value work.
Investors backing the round framed Checkbox as a foundational layer for modern legal operations, emphasizing orchestration across the legal technology stack and the ability to route and automate work as more legal tasks become AI-assisted. With the new funding, Checkbox plans to expand AI capabilities, deepen integrations, and scale adoption of its Legal Front Door approach across in-house teams.
To mark the financing, Checkbox is offering legal teams a no-cost opportunity to build their first AI agent for legal intake. The company also noted it has been named in Gartner’s 2025 Hype Cycle.
KEY QUOTES
“We’ve seen tremendous demand for the Legal Front Door and the market is really resonating with how we’ve uniquely solved this problem. Our customers go from operating in the dark and spending time on things they shouldn’t be, to working on what matters and getting visibility into demand, workload, and cycle times, which enables them to do better resource planning and demonstrate their value to the business.”
Evan Wong, Co-founder and CEO, Checkbox
“The Series A funding will fuel Checkbox’s vision to build a system of intelligence for legal work, turning everyday requests into institutional expertise. This institutional expertise can then be leveraged by AI to help teams move faster, deliver more consistent work, and reduce dependency on outside counsel.”
James Han, Co-founder and Chief Product Officer, Checkbox
“Tech implementations often fall short of expectations, but Checkbox really surprised us and exceeded our expectations. Usually, you’re relying on IT, and it would be a multi-year initiative to stand up something as robust as the legal front door, but with Checkbox, we were able to do it in just months with minimal IT support.”
Jeannine Moran, Director of Legal Operations, Hitachi
“Checkbox is defining the category for legal service management, a purpose-built orchestration layer that makes it possible to capture, manage, and automate legal work end-to-end. 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. Checkbox is building that future, and we’re thrilled to lead this round.”
Evan Wijaya, Principal, Touring Capital
