What startups get wrong about enterprise | Lindsey Scrase (COO, Checkr)

Lindsey Scrase, COO of Checkr, traces how a background in scrappy scaling at Google Cloud prepared her to join Checkr as CRO and then move to COO. She emphasizes humility about differences between mid‑market and enterprise selling: Google Cloud’s early GTM (a few hundred people, a few hundred million in revenue) taught her how to build ops, RevOps and systems from little, and at Checkr she found the company had more built but still needed the same operational rigor. Daniel (the CEO) hired her to be a hands‑on, data‑driven operator who could structure a multi‑segment go‑to‑market and lead the company’s push into enterprise accounts while avoiding the common mistake of assuming mid‑market playbooks will simply scale up.

The conversation pivots to concrete playbooks and tradeoffs for enterprise expansion. Scrase outlines what makes enterprise hard—year‑plus sales cycles, multi‑stakeholder decision processes, long tail product requests, and the need for targeted outbound and account‑based marketing—and prescribes focused vertical targeting, an embedded product manager on the enterprise team, and company‑wide commitment of engineering/product/legal/people resources. She recounts operational changes at Checkr: daily 30‑minute C‑staff huddles for rapid coordination, biweekly revenue reviews, a top‑20 silent‑read document cadence to problem‑solve, and twice‑yearly in‑person meetings for the top‑80 leaders to cascade strategy. On incentives, she describes shifting from bookings‑based rep pay to realized‑revenue comp for a consumptive pricing model to align rep behavior with customer success. Scrase also details practical AI deployments: generative AI for support and dispute resolution (goal: 90%+ resolution), measurable CSAT gains (~3x on AI interactions), an AI SDR/orchestration layer improving outbound pipeline, and ~8% of code written with generative tools. Throughout she stresses two consistent themes: get close to customers to supplement dashboards, and document decision rights (DRIs) so executives focus on the highest‑ROI decisions while pushing others down the org. The interviewer and Scrase broadly agree on the need for focus, cadence and aligned incentives; their only tension centers on calibrating process versus agility and how to set ambitious goals without destroying a sense of momentum.