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The Official SaaStr Podcast: SaaS | Founders | Investors
SaaStr 785: The Playbook for Going Upmarket with Stripe's CBO, Jeanne Dewitt Grosser, and Checkr's COO, Lindsey Scrase
Feb 12, 2025
Join Jeanne Dewitt Grosser, Chief Business Officer at Stripe, and Lindsey Scrase, COO at Checkr, as they share their insights on moving upmarket. They delve into effective strategies for startups transitioning to enterprise markets, discussing key indicators for this shift and the need for company alignment. Their experiences highlight the importance of understanding customer demand and managing unit economics efficiently. With actionable advice, they guide listeners on navigating the complexities of targeting enterprise clients successfully.
24:14
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Quick takeaways
- Recognizing key signals from existing customers is vital for determining the right moment to target enterprise clients.
- Successful enterprise transitions require holistic internal alignment and effective collaboration between sales, product, and engineering teams.
Deep dives
Identifying Signals for Moving Upmarket
Determining the right time to transition from serving startups to targeting enterprise customers is crucial for growth. Key signals include existing customers pressuring your company to provide more sophisticated offerings as they mature. Early wins in the enterprise sector are also essential; securing significant clients is more valuable than minor accounts, which is illustrated by the term 'whale' versus 'fin.' Stripe's experience in 2017, when they began engaging with enterprise clients like Amazon and growing startups, exemplifies the importance of recognizing these signals to effectively strategize for an upmarket shift.
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