SaaStr 785: The Playbook for Going Upmarket with Stripe's CBO, Jeanne Dewitt Grosser, and Checkr's COO, Lindsey Scrase

SaaStr 785: The Playbook for Going Upmarket with Stripe's CBO, Jeanne Dewitt Grosser, and Checkr's COO, Lindsey Scrase

SaaStr 785: The Playbook for Going Upmarket with Stripe's CBO, Jeanne Dewitt Grosser, and Checkr's COO, Lindsey Scrase

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.

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SaaStr hosts the largest SaaS community events on the planet.

Hey everybody - thanks to the 10,000 of you who came out to SaaStr Annual. We had a blast and big news -- we'll be back in MAY of 2025. That's right, the SaaStr Annual will be a bit earlier next year, May 13-15 2025. We'll still be back in the same venue, in the SF bay area at the 40+ acre sprawling san mateo county events center. Grab your tickets at saastrannual.com with code JASON50 for an extra discount on our very best pricing.

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Episoder(886)

SaaStr 879: Stripe's CRO of AI on The New AI GTM Playbook

SaaStr 879: Stripe's CRO of AI on The New AI GTM Playbook

175% Growth, 120 Countries, Agents as Buyers: Stripe's CRO of AI on The New AI GTM Playbook The fastest-growing AI companies are rewriting every rule in the GTM playbook, and Stripe has a front-row se...

23 Sep 43min

SaaStr 878: We Doubled Revenue with Agents. Here's Exactly How. (The Agents #014)

SaaStr 878: We Doubled Revenue with Agents. Here's Exactly How. (The Agents #014)

In the last 12 months, SaaStr went from a contact form and a generic follow-up email to a fully agentified revenue stack spanning inbound, outbound, and renewals. The result? Revenue doubled, new busi...

18 Sep 57min

SaaStr 877 CRO Confidential: 0 to $600M in Under 4 Years. The ElevenLabs GTM Playbook with Carles Reina

SaaStr 877 CRO Confidential: 0 to $600M in Under 4 Years. The ElevenLabs GTM Playbook with Carles Reina

CRO Confidential: 0 to $600M in Under 4 Years. The ElevenLabs GTM Playbook with Carles Reina (Partner @ Baobab Ventures and Former VP of Revenue at ElevenLabs). Hosted by Sam Blond, CEO and Co-Founder...

9 Sep 41min

SaaStr 876: Shipping Enterprise AI Agents with the CPOs of Rubrik, Glean, and Harvey

SaaStr 876: Shipping Enterprise AI Agents with the CPOs of Rubrik, Glean, and Harvey

SaaStr 876: Shipping Enterprise AI Agents with the CPOs of Rubrik, Glean, and Harvey Building AI agents is one thing. Shipping them to enterprise customers who will hold you responsible for every mis...

2 Sep 43min

SaaStr 875: Who Owns Your Data Now? Agents vs. System of Record, ServiceTitan vs. Podium, Headless Salesforce, and Agentic Renewals on The Agents #013

SaaStr 875: Who Owns Your Data Now? Agents vs. System of Record, ServiceTitan vs. Podium, Headless Salesforce, and Agentic Renewals on The Agents #013

SaaStr 875: Who Owns Your Data Now? Agents vs. System of Record, ServiceTitan vs. Podium, Headless Salesforce, and Agentic Renewals on The Agents #013 The agents are writing data faster than any human...

28 Aug 53min

SaaStr 874: From 0% to 83% AI-First Customers in 2 Years. How Owner's CEO Rebuilt a $100M Vertical SaaS Company

SaaStr 874: From 0% to 83% AI-First Customers in 2 Years. How Owner's CEO Rebuilt a $100M Vertical SaaS Company

What does it actually take to rebuild a $100M vertical SaaS company around AI - not just add AI features, but make AI the core of how your customers run their business? Adam Guild, CEO of Owner, share...

19 Aug 43min

SaaStr 873: Agents Are Your New Power Users: How Klaviyo CEO Andrew Bialecki Is Remaking a $1.4B Business for the Agent Era

SaaStr 873: Agents Are Your New Power Users: How Klaviyo CEO Andrew Bialecki Is Remaking a $1.4B Business for the Agent Era

Before AI, Klaviyo had an insight that changed e-commerce marketing forever: don't show merchants how many emails they sent, show them how much money those emails made. That single shift helped Klaviy...

14 Aug 43min

SaaStr 872: Our AI Agent Rewrote Our App Without Telling Us (The Agents #12)

SaaStr 872: Our AI Agent Rewrote Our App Without Telling Us (The Agents #12)

A year ago, running our agents took 30 minutes a day. This week: eight hours. Here's what changed - and why it's both thrilling and terrifying. In this episode, Amelia and Jason break down the week...

5 Aug 1h 4min

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