From Capitol Hill to the frontlines of financial innovation, Penny Lee has never stayed still for long. Her career—forged in campaign war rooms and crisis rooms alike—offers a compelling study in how modern leaders must adapt and lead through change.
By any standard, Lee’s career trajectory is an ambitious one. She has advised governors and senators, helped steer the U.S. through the 2008 financial crash, and now serves as President and CEO of the Financial Technology Association (FTA), representing the voices of fintech giants like PayPal, Stripe and Chime, and advocating for gender equity in the workplace.
But while her résumé reads like a masterclass in public and private influence, Lee is quick to point out that the real story lies in the transitions and in the discomfort of learning how to lead when the rulebook no longer applies.
In Episode 15 of Pivot Points, she joined Founder Dave Allen to unpack the moments that defined her and the leadership lessons she carries forward.
Leading through crisis
In late 2008, Lee was serving as a senior advisor to Senate Majority Leader Harry Reid when the financial markets began to unravel. She had just returned from campaigning in Pennsylvania for then-presidential candidate Barack Obama when the full scale of the crisis became apparent.
“I’ll never forget being in the room when then-Secretary Paulson said, ‘The Lehman Brothers you know tonight will not exist tomorrow,” she recalls.
Suddenly, Lee was helping craft urgent legislation in a climate of fear and economic collapse. In those moments, there was no playbook—only instinct, pressure, and the need for clear-headed leadership.
She points to Reid as a pivotal influence. “He didn’t need to be liked. He needed to be trusted. That gave him the power to say no, and people respected him more for it.”
It was a formative period. Lee learned that leadership, especially in crisis, isn’t about certainty but about moving forward despite the unknowns. This led her to face a different kind of crossroads. Despite being offered a senior role in the Obama White House, she made the intentional decision to leave public service.
“I took the time to ask myself: what kind of job would motivate me? What kind of culture would allow me to lead and thrive?”
The transition wasn’t easy. Moving from government—where she had access, authority, and insider knowledge—to the private sector meant starting over. As she put it: “In government, you’re a buyer. In the private sector, you’re a seller. That shift requires humility and a complete change in mindset.”
This period of growth laid the groundwork for her biggest leap yet.
I took the time to ask myself: what kind of job would motivate me? What kind of culture would allow me to lead and thrive?Penny Lee
President and CEO, Financial Technology Association (FTA)
Building credibility fast
In 2021, Lee was approached to lead a new national trade association that would represent the fast-moving, often misunderstood fintech sector in Washington.
With no blueprint and no team, she began building the Financial Technology Association (FTA) from the ground up. The timing was not without challenge. Fintech was drawing increasing scrutiny from regulators, and trust in new financial technologies was far from guaranteed.
Lee’s job was to build credibility—fast. That meant aligning members, influencing policy, and making the case that innovation and consumer protection could coexist.
“This job brings everything together: my policy background, my campaign experience, and my belief in creating something bigger than yourself.”
Leading the Financial Technology Association has given Lee not only a professional platform but a personal mission. At the FTA, she can advocate for responsible innovation, influence meaningful policy, and create space for underrepresented voices—all while building an institution from the ground up. Now, she is a passionate advocate for gender equity, particularly in spaces where access to capital and influence remains imbalanced.
In 2013, she co-founded an angel investment group designed to address the stark funding gap faced by women founders in tech and beyond. The numbers, she points out, remain dismal: “It’s still 98 percent of funding to men, 2 percent to women. That doesn’t change on its own—you have to intentionally break the cycle.”
For Lee, equity isn’t a sideline issue. It’s fundamental to modern leadership. At the FTA, she has made it a priority to hire for potential, not pedigree, and to build inclusive teams that reflect the diversity of the people their work affects.
“Some of the best people I’ve hired didn’t have the perfect résumé. They just hadn’t had access yet. We need to look harder, not just look familiar.”
Her leadership is grounded in the belief that equity and excellence go hand-in-hand, and that it’s a leader’s responsibility to create opportunity, not just occupy it.
It’s still 98 percent of funding to men, 2 percent to women. That doesn’t change on its own—you have to intentionally break the cycle.Penny Lee
President and CEO, Financial Technology Association (FTA)
Leadership lessons
Lee distilled her leadership philosophy into a series of powerful takeaways:
1. Be consistent in your convictions.
Leadership isn’t about popularity, but predictability. In times of uncertainty, people want to know where you stand.
2. Learn to say no, firmly and clearly.
A strong ‘no’ is more valuable than a vague ‘yes.’ This lesson, drawn from her time with Harry Reid, is central to how she builds trust and sets boundaries.
3. Reflect before you pivot.
Lee’s decision to leave government was driven not by opportunity, but by intentional reflection—something she urges other leaders to prioritize.
4. Hire for potential, not polish.
Be passionate about equity and inclusive hiring, particularly in sectors like tech and finance, where homogeneity still dominates.
5. Extend grace when people stumble.
A culture of compassion that allows room for growth is essential for long-term leadership success.
Lee’s career is a masterclass in leading through change. It’s a model for any leader navigating uncertainty in a world that increasingly rewards not just resilience, but reinvention. Listen to the full conversation on our Pivot Points podcast—out now.
