When Steve Holm walked back through Copper's doors in August 2023, he wasn't walking in as a stranger. He'd been employee #4 - the first person to own product and design at a scrappy San Francisco startup then called ProsperWorks. He'd watched it go from a Google Workspace integration with a big idea to a $25M ARR business over five years. Then he left.
He went to scale. First Dropbox, where he led the ecosystem team - building APIs, building a marketplace, learning how a company with real infrastructure actually runs. Then Podium, a Utah-based CRM for local businesses, where he became SVP of Product Design. He was doing well. He wasn't supposed to come back.
But he noticed something from the outside. Copper had shifted. The product soul that made it different - the deep Google Workspace integration, the zero-input data entry philosophy, the obsession with simplicity - had gotten buried under enterprise ambitions and a team hired to execute a strategy that didn't fit the company. Churn was outpacing growth. Three departments were pulling in different directions.
So the board called. And this time, he came back as CEO.