Todd Olson went from two failed startups to building Pendo, a SaaS platform now generating $200M ARR with 880 employees and nearly $500M raised.

In this episode, Todd reveals how early mistakes shaped his obsession with product-market fit, why he refused to hire salespeople until he validated the sales motion himself, and how creating an entirely new category forced him to abandon inbound marketing for manual outreach. He also explains the controversial pricing decision—raising the minimum from $99 to $1,000 overnight—that changed the company's trajectory forever.

🔑 Key Lessons

• 💡 Product-Market Fit Obsession: Why Todd refused to scale until he had undeniable fit, unlike his first two startups.


• 💰 The 10x Price Hike: How raising the minimum price from $99/mo to $1,000/mo filtered out bad customers and accelerated growth.


• 🤝 Founder-Led Sales: Why Todd personally sold the first $500k in ARR before hiring a single salesperson.


• 🏗️ Building the MVP: How Pendo launched with critical features (Auto-Track) that competitors like Segment ignored for years.


• 🚀 Category Creation: The challenge of selling a product nobody was searching for and why "Product-Led Growth" didn't work early on.

📖 Chapters

• Introduction & Favorite Quote


• What is Pendo? Product Overview


• Company Metrics


• Todd’s Early Coding Career


• First Startup Failure & Lessons


• Missing Product-Market Fit


• Inspiration for Pendo


• Building the First Product


• Landing First Customers


• First Paying Customer


• Pricing Evolution


• Hardest Challenges Scaling


• Lightning Round

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Resources:

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