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
