Leading with Values: Jessica McKellar, CEO and Founder of Pilot on Building Trust Through Personal Connection : Women in Tech San Francisco

Leading with Values: Jessica McKellar, CEO and Founder of Pilot on Building Trust Through Personal Connection : Women in Tech San Francisco

April 20, 2026 · 46 min · Episode 734

About this episode

Jessica McKellar discusses her journey as a tech entrepreneur and the importance of personal connection in leadership.

Welcome back to the Women in Tech podcast, where we celebrate incredible women accelerating in the world of technology. In today’s episode, we’re joined by Jessica McKellar, CEO of Pilot, a tech company dedicated to relieving the financial stress of small business owners through innovative finance and accounting solutions. From her early days as a engineering student at MIT to building three companies—two of which were acquired—and now leading hundreds of employees at Pilot, Jessica McKellar brings an inspiring perspective on leadership, resilience, and redefining work-life harmony as a founder and mother. She shares candid insights about the personal side of entrepreneurship, the challenges of scaling, and how passion for solving real-world problems motivates her every day.

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