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

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/