What startups get wrong about enterprise | Lindsey Scrase (COO, Checkr)

About this episode

In the latest episode of Executive Function, Brett sits down with Lindsey Scrase, COO of Checkr. Before joining Checkr as CRO and later stepping into the COO seat, Lindsey spent nearly a decade at Google Cloud as global managing director for SMB, mid-market, and startups. In this conversation, she breaks down why moving upmarket into enterprise trips up so many startups looking to scale, how Checkr rebuilt its sales compensation model to keep pace with growth, and where AI is already reshaping her operations and go-to-market teams. In today's episode, we discuss: Why operators who thrive at massive-scale companies often struggle when they join a startup The hard-won lessons from Checkr's early enterprise push that nearly failed Why Checkr’s C-suite meets every morning with no specific agenda The surprising challenges moving from CRO to COO How Checkr turned AI experiments into operating systems References Amazon: https://www.amazon.com Checkr: https://checkr.com Claude: https://claude.com Daniel Yanisse: https://www.linkedin.com/in/yanisse/ DoorDash: https://www.doordash.com Google: https://www.google.com Lovable: https://lovable.dev Micr