How Multiple Pivots positioned Checkbox as the Legal Front Door for Corporations

Hear how Checkbox's CEO pivoted multiple times over nearly a decade before landing on the positioning that unlocked enterprise clients and major funding.

Evan Wong has spent nearly a decade building Checkbox, pivoting multiple times before landing on legal automation and enterprise traction. In this fireside chat, he'll walk through what didn't work, how he evaluated each pivot, and the positioning shift that unlocked customers like SAP and Hitachi. You'll hear practical frameworks for assessing whether to pivot, plus insights from bootstrapping and raising $23M. This is straight-from-the-founder perspective on timing, persistence, and catching a market wave at the right moment.