Scaling without losing speed is harder than it looks — especially when you're chasing enterprise customers and building an AI-native platform. Lindsey Scrase, Chief Operating Officer of Checkr, Inc., reveals how her customer-first mindset, forged during her tenure at Google Cloud, is driving Checkr’s transformation into a core hiring infrastructure platform while scaling AI across operations. With a track record of building high-velocity GTM motions and a strong commitment to second-chance hiring, she explains what it takes to evolve into an AI-native enterprise.

Specifically, Lindsey covers:

(03:55) Early-stage Google Cloud, then called Google Apps.

(06:46) How a culture of wearing multiple hats inspired continuous improvement.

(10:40) Early execs need curiosity and first-principles thinking over fixed playbooks.

(15:57) A shift from gig-focused roots to strong SMB and mid-market segments.

(21:39) Strong leaders think long-term and dive deep into day-to-day details.

(27:16) Enterprise growth demands tight alignment across GTM, product and CS.

(31:25) AI will become table stakes as true adoption goes beyond branding and hype.

(35:25) Generative AI chat boosts CSAT by delivering instant, contextual responses.

(41:13) Take bigger swings earlier and don’t take things so seriously.

(45:01) Direct feedback builds trust and prevents conflict from turning toxic.

Resources Mentioned:

Lindsey Scrase

https://www.linkedin.com/in/lindsey-scrase-0702442/

Checkr | LinkedIn

https://www.linkedin.com/company/checkr-com/

Checkr | Website

https://checkr.com/

Truework

https://www.truework.com/

“Working Backwards” by Bill Carr and Colin Bryar

https://www.amazon.com/Working-Backwards-Insights-Stories-Secrets/dp/1250267595

“The Five Dysfunctions of a Team” by Patrick Lencioni

https://www.amazon.com/Five-Dysfunctions-Team-Leadership-Fable/dp/0787960756

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241: Alison MacLeod, The Blind Poet Dave Steele and Lisa Hall