Rob Woollen spent seven brutal years with almost zero revenue before finding product-market fit. Then, after finally hitting $1M ARR, he made the gutsy call to rebuild the entire product from scratch. In this episode, early-stage B2B SaaS founders will learn the reality of the long search for product-market fit.
Rob breaks down exactly how a single lunch with Snowflake's CEO changed everything. You will learn why founders must be "entirely irrational," how to recognize real product-market fit signals vs. polite feedback, and why he rebuilt at $1M ARR when most founders would celebrate.
In this episode, Rob also shares how losing two founding engineers after 10 months nearly killed the company, and why the quarter after they thought they had product-market fit resulted in zero sales.
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🔑 Key Lessons
- 🎯 Stay focused on the problem, pivot on the solution: Sigma never changed the problem they were solving—only the interface. Seven years of iteration finally led to product-market fit.
- 🧠Founders must be "entirely irrational": If someone can talk you out of starting a company, you shouldn't start one.
- 🔄 Rebuild even when you're winning: At $1M ARR, Rob made the controversial call to rebuild because the interface "still wasn't quite right."
- 💡 One passionate response beats a hundred polite ones: When Snowflake's CEO said "I want this—when can I start using this?" they knew they'd found something real.
- 📉 Product-market fit isn't a light bulb moment: After closing deals three days in a row, the next quarter was zero sales.
Chapters
- Introduction and what Sigma Computing does
- The tale of two companies: 7 years of zero revenue
- Raising $8M and the first seven years of iteration
- Building the team and the first "colossal failure" prototype
- Losing two founding engineers and shrinking to three
- Why founders must be "entirely irrational"
- The Snowflake meeting that changed everything
- The messy reality of product-market fit
- Building champion relationships and early traction
- Deciding to rebuild the product at $1M ARR
- Founder intuition vs. data-driven decisions
- The partnership flywheel with Snowflake
- How it feels after seven years of persistence
- Lightning round: books, habits, and advice
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