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