What startups get wrong about enterprise | Lindsey Scrase (COO, Checkr)
Summary
The guest discusses transitioning from large-scale tech to startups, emphasizing the challenges of expanding into enterprise markets. Key topics include the necessity of focused vertical strategies, cross-functional alignment, and rigorous decision-making frameworks. The conversation also covers the enduring value of in-person events for building trust and the critical role of aligning sales incentives with actual revenue realization rather than just bookings.
Topics discussed
Background: From Google Cloud to Checkr's first CRO
Challenges of building enterprise sales at a startup
Why enterprise sales is harder than mid-market
Strategy for targeting and winning enterprise accounts
The role of events and trust in enterprise buying
Leadership dynamics: CRO/COO and decision-making frameworks
Aligning incentives and sales compensation models
Traits of top-performing sales leaders
Operational rituals and organizational alignment
Data-driven insights vs. customer intuition and metrics
Leveraging AI for operations, sales, and engineering
Career path from sales leader to COO
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