Episode
From 0 to $5B: Scaling Enterprise in the AI-Native Era with Lindsey Scrase, Checkr
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- Traction Podcast
- Published
- Jul 23, 2025
- Duration seconds
- 2822
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Summary
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…