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From 0 to $5B: Scaling Enterprise in the AI-Native Era with Lindsey Scrase, Checkr
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:
https://www.linkedin.com/in/lindsey-scrase-0702442/
Checkr | LinkedIn
https://www.linkedin.com/company/checkr-com/
Checkr | Website
https://checkr.com/
https://www.truework.com/
“Working Backwards” by Bill Carr and Colin Bryar
https://www.amazon.com/Working-Backwards-Insights-Stories-Secrets/dp/1250267595