Checkbox announced a $23 million Series A, 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, Head of Agentic AI at Workday and former Co-Founder and CEO of Evisort. The investment will be used to expand Checkbox's AI Legal Front Door to replace fragmented, manual legal intake with intelligent, automated workflows across the enterprise.