Rob Woollen founded Sigma Computing with $8M in funding and a massive vision, but for the first seven years, the company generated almost zero revenue. They built products that failed, lost early team members, and struggled to find a working interface.

In this episode, Rob (Co-founder & CTO) reveals how they survived the "Valley of Death" to eventually hit product-market fit so hard they grew from $0 to $100M ARR in just 3.5 years. He breaks down why their early "AI Suggestions" product failed, how a lunch with Snowflake's CEO changed their trajectory, and the specific "Spreadsheet Interface" insight that finally unlocked the enterprise market.

🔑 Key Lessons

• 📉 The "Tale of Two Companies": How Sigma survived 7 years of stagnation before finding the fit that led to $100M ARR.


• 💡 The Interface Pivot: Why their initial "AI Auto-Analysis" product failed and why returning to a "Spreadsheet" interface won the market.


• 🤝 Strategic Partnerships: How piggybacking on Snowflake's growth (and solving their biggest user gap) fueled Sigma's explosion.


• 🧠 Founder Resilience: Rob's mindset during the "dark years" when the team shrank to 3 people and the office was empty.


• 🏢 Enterprise Sales: How they transitioned from founder-led sales (giving out personal cell numbers) to a scalable enterprise motion.

📖 Chapters

• Introduction and Favorite Quote


• Overview of Sigma Computing


• Company Growth and Milestones


• Founding Story and Background


• Early Challenges and Iterations


• Securing Funding and Initial Team


• Product Development and Prototypes


• First Startup Failure & Lessons


• Missing Product-Market Fit


• Inspiration for Pendo


• Building the First Product


• Landing First Customers


• First Paying Customer


• Achieving Product-Market Fit


• Rebuilding the Product for Broader Appeal


• Leveraging Strategic Partnerships


• Reflecting on the Journey and Key Milestones


• Lightning Round: Insights and Personal Reflections

This episode is brought to you by:

💖 Gearheart → Book a free strategy session + get 20% off select services

📫 Mailtrap → Get 20% off with code THESAASPODCAST

Resources:

🎧 Full Show Notes: saasclub.io/448

🎤 Subscribe to the Podcast: saasclub.io/subscribe

💌 Get weekly 5-minute SaaS insights: saasclub.io/email

💡 Join the SaaS Club founder community: saasclub.co/plus