BEYOND THE CHAIR

Reimagining Retirement with Penelope

In a country where over 30 million small business owners are overlooked by traditional retirement platforms, Penelope is flipping the script. In this Beyond the Chair spotlight, we sit down with Jean Smart, Founder & CEO of Penelope, to talk about why the smallest businesses deserve the biggest innovation in retirement and how Penelope is delivering just that.

Penelope is a retirement savings platform designed for sole proprietors, micro-businesses, and the intermediaries who serve them. The company’s mission is simple but powerful: make retirement plans accessible, affordable, and ridiculously easy to implement for those who have historically been left out of the conversation.

“There are 34 million businesses in the U.S. Only 700,000 401(k) plans. That math is a problem we’re here to solve.”

Jean, a former Wall Street executive and now a mission-driven fintech leader, has built Penelope to remove the friction—technical, administrative, and emotional—that prevents small business owners from planning for their future.

An Intentional Path with TFC

Jean’s journey with The Founder’s Chair began at the Irvine event, where she immediately felt a different kind of energy. From the due diligence process to the in-person experience, Jean recalls the value of having investors truly listen—not just to her pitch, but to her data room, her story, and her strategy.

That connection led to more than investment. It unlocked strategic partnerships, pitch opportunities, and access to the broader insurtech ecosystem.