April 20, 2026

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

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.

Show Notes

In this inspiring episode of Women in Tech, Jessica McKellar, CEO of Pilot, joins us from San Francisco to share her journey from MIT computer club to serial entrepreneurship. She dives into her mission of democratizing finance and accounting for small businesses, the emotional side of entrepreneurship, finding purpose in work, family-life philosophy, and what keeps her striving for more. This candid conversation is packed with wisdom for women forging their own path in tech, emphasizing the podcast’s mission: “If She Can Do It, So Can I.”

Featured Guest

Jessica McKellar — CEO of Pilot

Key Topics Discussed

Entrepreneurship & Personal Growth:
Jessica McKellar discusses starting three companies, her long-time business partnership, and why she remains passionate about solving real problems for business owners

The Human Side of Bookkeeping:
The emotional and vulnerable journey that clients experience with their finances, including powerful customer stories about overcoming shame and gaining confidence

Career Acceleration:
How coming to computer science “late” led Jessica McKellar to push herself, embrace startups, and thrive in leadership despite challenges

Leadership & Team Building:
Jessica McKellar's values-driven approach to building and managing teams, emphasizing autonomy, high standards, and staying close to the customer experience

Work, Life, and What “Balance” Really Means:
Honest insight into how Jessica McKellar juggles life as a CEO and mom — rejecting prescriptive advice and carving out a deeply fulfilling routine

Resilience & Overcoming Obstacles:
Navigating leadership transitions, the emotional labor of managing a growing company, and building the “capacity” to support both teams and family

Fundraising & Profitability:
Real talk about inequity in fundraising, embracing sales as a superpower, and the importance of confidence for women founders

Mentorship, Support, and Thick Skin:
Building a network of personal and professional support, sustaining motivation, and learning to rise above gendered criticism online

Personal Recommendations:

Old-school edutainment games for kids (Math Storm, Reader Rabbit, Number Munchers)

Podcasts: Search Engine, Freakonomics Radio

Tools: Whisper Flow for AI dictation

Notable Takeaways

“The times in my life when I have felt burnt out were not related to how long I was working… It was about being in situations where I didn't like the situation that I was in and I couldn't get out of it, where I lacked the autonomy to resolve a thing that was causing stress or pain.”

“Your job is sales. So get ready to love it.”

“My goal in life is to leverage the capabilities that I have in the world to make it a little bit better.”