Ryan Wang made a SaaS pricing mistake that nearly killed his company. As CEO of Assembled—a workforce management platform for support teams—he chose usage-based pricing with no minimums. The result? Eight months without a single dollar of revenue while burning through runway. In this episode, early-stage B2B SaaS founders will learn the brutal reality of SaaS pricing mistakes and how to fix them.

Ryan breaks down exactly how he fixed his SaaS pricing model after the initial failure. You will learn why usage-based pricing needs guardrails, how he convinced Stripe to become his first paying customer, and the "shadow org chart" approach to enterprise sales.

In this episode, Ryan also shares why Assembled hired senior leaders earlier than most startups recommend, and how his background at Stripe shaped his approach to building enterprise software.

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🔑 Key Lessons

• 💰 SaaS pricing without minimums is dangerous: Usage-based models need floors to ensure revenue predictability—Ryan learned this after 8 months of zero revenue.


• 🏢 Hire senior leaders earlier than feels comfortable: They bring playbooks and credibility you can't build alone.


• 🗺️ Build the "shadow org chart": Map decision-makers and influencers before pitching to close enterprise deals faster.


• 🎯 Your first customer shapes your product: Choose someone who represents your ideal future customers—Stripe set the standard for Assembled.


• 🤝 Trust compounds in enterprise sales: Early champions become references for future deals.

Chapters

• Introduction and Ryan's background at Stripe


• The pain point that led to Assembled


• Why usage-based SaaS pricing with no minimums failed


• Eight months without revenue—surviving the runway crisis


• How Ryan fixed the SaaS pricing model


• Landing Stripe as the first paying customer


• The shadow org chart approach to enterprise sales


• Hiring senior leaders early


• Scaling to 8-figure ARR


• Lessons learned and advice for founders

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Resources

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