Pendo

Eric Bourne and Todd Olson met at college studying computer engineering. After graduation, Eric started a web-based consulting business building websites for clients and brought Todd on as his first employee. Recognizing Todd's value, Eric made him a co-founder, giving him 20-30% equity to normalize his position—a fair decision that proved foundational to Pendo's future.

The founding team (which grew to four co-founders) decided to pivot from consulting into product. They raised approximately $500,000 in angel funding to help kickstart the transition. Their initial product was minimal—just 1% of what Pendo eventually became—but it solved a real problem: helping companies understand user behavior within their applications.

On January 9, 2015, Pendo received their first check from ShowClicks for $5.97. Given their $99/month entry-level pricing, this likely represented a discounted or partial subscription. The payment came via physical check—a reminder that in 2015, some companies still operated this way. Interestingly, Pittsburgh became their biggest market initially, which surprised even Eric given it wasn't known as a major SaaS hub. But customer geography quickly shifted as they grew: Raleigh, then Boston, New York, and San Francisco.

By Q4 2017, when Pendo hit $13.4M ARR, their marketing machine was well-oiled. A webinar co-hosted with UserVoice generated 1,272 leads at just $5 per lead—compared to their pro forma expectation of 300 leads for $6,500 in promotion spend. While webinars produced smaller deal sizes initially, the sheer volume of qualified leads built their mailing list, community, and brand awareness. Website traffic and in-person events were the other top pipeline drivers that quarter.

Eric championed webinars despite skepticism from board members and advisors who thought the tactic was outdated. His response was simple: "Look at my numbers. When they stop working, we'll stop doing them."

Productivity marketing became another turning point. When they were losing 50-50 competitive bids against WalkMe, Eric's team didn't try to copy WalkMe's advanced guide features. Instead, they leaned into Pendo's unique strength: analytics. They built a compelling positioning narrative: guides without analytics are ineffective because you can't target them to the right users based on behavior. This messaging shift, combined with kill sheets for competitors shared across the sales team, swung win rates back in their favor—worth roughly $15M in enterprise value at their valuation multiples.

Brand building also proved crucial. Early on, they branded the color pink as Pendo's own. The payoff was unexpected: attendees at conferences they didn't even sponsor would see someone in pink and assume Pendo was there, generating impressions and awareness from shows they weren't even at.

By 2021, Pendo surpassed $200M in revenue—more than double the 2017 figure. Eric stayed through approximately $130-140M ARR in 2022 before stepping down (Todd remained CEO and majority shareholder). Eric's next venture is 24andUp, a venture studio model where he co-creates companies from scratch. Of the four studio companies launched so far, three have raised external funding. In 2022, when Eric left, Pendo had raised around $300M across multiple funding rounds, with the last public valuation at $2.6B. The company is now targeting an IPO, with Todd committed to building another public software company in Raleigh.