Scaling up an established company with active PE investors involved is a totally different sport than starting and growing a crazy bootstrapped SaaS company.
When you sell most of your SaaS company to private equity acquirers, a new CEO will eventually come in to run it.
Most founders don’t want to play the “grow big with big investors” game, so new CEOs come in who like this particular scale-up game.
Steve Oriola isn’t the founder of Unbounce. He’s the CEO that Crest Rock Partners brought in to run and transform it.
A sales-and-marketing software veteran who spent a decade at Constant Contact and even ran Act! for a spell. Act! is the product and company I helped grow and run myself 10 (and 20) years earlier!
Steve joined Unbounce in January 2024 and acquired the Insightly CRM six months later, merging the two into one company and one culture.
Today Unbounce is a roughly 200-person business combining a landing-page and conversion-rate-optimization marketing platform with a sales-focused CRM and integrated project management.
Owned by private equity (Crest Rock Partners) with the founders still on the board, the company had to get smaller to find its focus — scoping down to its core value before rebuilding around agentic AI.
Steve is now steering a full transformation toward “service as software,” which includes professional services and forward-deployed engineering that surface repeatable IP, then harden into managed services with governance for agents.
He is comfortable on both sides of the table, translating between investors who “operate in Excel” and the humans who run the business and have a different perspective.
As Steve describes it:
“The trickiest part of being a CEO is which side of the table you’re on. Are you on the side of the employees who work for you, with your investors and your board on the other side? Or are you on the investor side, looking at the company and making the rational decisions that are best for them?
“If you’re a founder, you’re on the team side of the table. But you’ve got to understand the investors’ perspective, because to some degree you’re managing them. They’re not running your business, and they’re very dependent on you.
“Really, it’s empathy. You have to understand what they’re dealing with, because they can make bottom-line decisions that don’t feel very human. They’re operating in Excel, and you’re dealing with humans. So you’re the mediator between humanity and cold-hearted business.”
After selling two companies I helped build and grow to much bigger software companies, I stayed on for a few years to lead those businesses inside each of those bigger companies. I played the big-company game as long as I could, then went back to starting and building new things again.
Check out this practical interview with Steve Oriola on the Practical Founders Podcast.
