The Playbook for Going Upmarket with Stripe's CBO and Checkr's COO

SaaStr AI February 12, 2025
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Want to know when to move upmarket and how to actually pull it off? Jeanne Dewitt Grosser, Chief Business Officer at Stripe, and Lindsey Scrase, COO at Checkr, have done it multiple times at companies like Google Cloud, Stripe, and Checkr. They came to SaaStr Annual to share what they’ve learned about making the move to go more enterprise actually work. They dive into their professional histories, strategies for startups when targeting and pivoting to enterprise markets, and the signals to watch for before making the leap. Learn from their experiences, including the importance of an aligned company push, the evolution of pricing, and tips for managing unit economics efficiently. Don't miss their actionable advice on understanding unit economics and building a solid operating model to enhance your business success. 00:00 Introduction and Speaker Backgrounds 02:26 The Importance of Moving Upmarket 03:00 Signals for Moving Upmarket 06:22 Challenges and Strategies for Enterprise Transition 13:36 Pricing and Packaging for Enterprise 14:57 Efficient Growth and Metrics 20:26 Key Takeaways and Conclusion --------------------------------------------------------------------------------------------------------- Want to join the SaaStr community? We're the 🌎largest community for B2B software. Subscribe for weekly updates: https://www.saastr.com/subscribeform Twitter: https://twitter.com/saastr LinkedIn: https://www.linkedin.com/company/2724976 Quora Group: https://www.quora.com/q/cloud Facebook: https://www.facebook.com/SaaStr/ Instagram: https://www.instagram.com/saastr/ Our North American Event: https://bit.ly/2OXeAYh Our European Event: https://bit.ly/2OZTad8

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