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
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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.
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Timing the Enterprise Move
- Don't pivot to enterprise just for a bigger TAM or higher growth rate.
- Wait for genuine signals from the market.
Signals for Upmarket Move
- Two strong signals indicate it's time to move upmarket: existing customers' growing needs and meaningful enterprise wins.
- Winning small, experimental projects doesn't count as true enterprise success.
Stripe's Enterprise Entry
- Stripe began its enterprise journey in 2017 as clients like Shopify and Lyft matured.
- Winning Amazon.com in Singapore solidified their enterprise potential.