One bold message can change your entire career trajectory and it doesn’t have to be perfect to be powerful.
We sit down with Trish Gillis, Director and Senior Product Manager for Cash Pro at Bank of America, to unpack what a real career pivot looks like when you start in traditional finance, jump into a high-growth startup like Glossier, and return to financial services with a stronger point of view and sharper skills.
We get into the practical mechanics behind a successful pivot: spotting what’s missing in your day-to-day, recognizing transferable skills, and choosing risk at the right time in life. Trish shares what startup culture taught her about scaling, moving fast without a safety net, and balancing excitement with responsible decision-making. We also talk about the creative side of technology and product management, from brainstorming “forward inventing” sessions to building a workplace where people feel safe enough to share ideas and challenge assumptions.
Trish also explains how innovation changes when you’re thinking beyond today’s problems, including her experience as a patent holder and how teams can plan for what’s next in fintech, digital banking, AI, and client experience. If you’ve ever looked at a job posting and talked yourself out of applying, this conversation will reset how you evaluate your own skills.
