
Todd Olson, Pendo
How He Found SaaS Product-Market Fit After Two Failures
Todd Olson is the founder and CEO of Pendo, a product experience platform that helps software companies understand user behavior and improve their applications. In the late 1990s, during the dot-com boom, Todd started his first company which eventually led to a promising acquisition offer. But the board thought Todd and his co-founder were too young to handle negotiations themselves. So they brought in someone else. The deal fell apart, the company pivoted to services, and Todd ended up leaving. His next startup struggled from the start. Todd made what he now calls an idiotic mistake. He assumed CEOs had to be non-technical, so he gave the role to a sales guy friend. They couldn't find product-market fit. Rally Software eventually acquired them, which Todd describes as a good soft landing more than a success story. Todd stayed on at Rally as head of product. That's where he discovered the problem that would become Pendo. He had no visibility into how users were actually using their product. He couldn't guide them when they got stuck. So in 2013, he left to build the solution he wished he had. This time, Todd obsessed over product-market fit from day one. He built auto-tracking into Pendo so customers didn't need developers adding tracking code everywhere. But nobody was searching for "product analytics plus in-app guidance." The category didn't exist. With inbound marketing not an option, Todd went manual. He leveraged his VC network for introductions and started messaging heads of product on LinkedIn. For the first year, he focused on the number of installs as the most important metric. By October 2014, Todd noticed one company using Pendo constantly. He called them and closed his first paying customer at $500 a month. Today, Pendo generates over $200 million ARR with about 880 employees and has raised over $479 million to date. Todd's journey from two failed startups to product-market fit at scale is a masterclass in validating before scaling.






















