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 Microsoft: https://www.microsoft.com Where to find Lindsey LinkedIn: https://www.linkedin.com/in/lindsey-scrase-0702442/ Twitter/X: https://twitter.com/Lscrase Where to find Brett LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/ Twitter/X: https://twitter.com/brettberson Where to find First Round Capital Website: https://firstround.com/ First Round Review: https://review.firstround.com/ Twitter/X: https://twitter.com/firstround YouTube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast Timestamps 00:00 Introduction 00:06 Why big-company executives often struggle in startups 02:18 What Checkr's first CRO needed to accomplish 03:33 How to take on an entrenched category leader 06:58 Why leaders underestimate how hard the jump to enterprise really is 10:23 Separating a true deal-blocker from a customer's nice-to-have request 18:30 Why Lindsey hired enterprise-scarred sales leader over a market leader's résumé 22:08 The biggest challenges of moving from CRO to COO 28:03 Why Checkr names a single decision-maker for every major decision 34:42 Why Checkr rebuilt their sales compensation model 40:39 What actually separates a team's best seller from everyone else 45:03 Inside Checkr’s daily, no-agenda, c-suite meeting 50:23 How following data can sometimes lead you in the wrong direction 57:27 Why hitting 130% of a goal isn’t always a good thing 58:57 Where AI has changed how Checkr's teams operate day to day 1:04:33 Advice for all aspiring COOs

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