It started with conversations that Wendy Cai-Lee described as "free therapy sessions" with Jennifer Docherty, a friend who is general counsel at Performance Trust Capital Partners, an advisory firm that focuses on banks.
At Docherty's suggestion, they started inviting more women leaders to participate. Over the last 18 months, the sessions have grown into a circle of roughly 20 female bank executives in the New York area. They gather regularly for food and off-the-record conversations, providing something of an alternative to the Wall Street boys club. They discuss everything from the best way to strengthen relationships with board members to managing regulatory expectations.
"It's as organic of a thing as you can imagine," said Cai-Lee, founder and CEO of New York-based Piermont Bank. "But it says a lot about the need."
Cai-Lee, for example, reached out to chief risk officers in the group when she needed recommendations for vendors that could assist the $596 million-asset Piermont with recent regulatory challenges. "It's made that process exponentially easier and more productive," she said.
As it has with other banks, the Federal Deposit Insurance Corp. entered into a consent order with Piermont in early 2024 that requires the bank to improve oversight of its fintech relationships. The bank has been a leader in providing banking services and infrastructure to fintechs.
Despite the regulatory headwinds, Cai-Lee remains committed to innovation. "That commitment is actually even more important when you're being criticized," she said.
Banks aren't innovating for fun or because they want the "latest, shiniest toy," she said. Innovation is critical for the financial industry's evolution. Rather than backing off in the face of regulatory scrutiny, she said, banks can address what needs to be corrected, make regulators comfortable and then figure out how to move forward.
With that in mind, Cai-Lee remains convinced that Piermont must take a leadership role in supporting women entrepreneurs, who often struggle to attract capital and investors.
Roughly 2% of all venture capital funds go to women-led startups. The challenge has grown steeper following last year's collapse of Silicon Valley Bank and Signature Bank, which made it harder for smaller VC funds focused on women and minority founders to find banking partners.
Piermont, which opened in July 2019, is tackling the issue by creating events and products for founders and investors. "It's not one or the other," Cai-Lee said.
She worked with the Piermont team, for instance, to shift more resources into lending to smaller investment funds, with a focus on funds managed by women and minority founders. The bank also strengthened efforts to lend directly to those founders. As an example, the bank extended a $10 million line of credit to a tech-enabled real estate investment fund founded and led by an Asian American woman.
Cai-Lee brings more than banking experience to the effort. She started and sold her first company when she was in her 20s. As a result, founders see her not just as a banker trying to pitch them loans but as someone who understands what it's like to get a startup off the ground.
"I always feel like there's so much more to do" for underserved entrepreneurs, she said.
