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

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.” Resources & Mentions Pilot — Providing affordable, tech-powered finance and accounting support for small businesses. Episode Highlights Timeline 00:01:18 — Customer stories and the personal side of accounting 00:04:16 — Engineering background, business partnership, and why bookkeeping 00:10:33 — Entering tech and overcoming imposter syndrome 00:14:04 — Leadership style and the importance of detail 00:17:17 — Surviving hard transitions and building capacity 00:23:37 — On work, life, and living without “balance” 00:27:28 — Burnout and agency 00:32:03 — Fundraising tips for founders 00:37:25 — Responding to gendered feedback and building self-trust 00:40:42 — Favorite podcasts 00:43:00 — Old-school educational games for kids Join Us Be inspired by more global stories of women accelerating in tech — because "If She Can Do It, So Can I."

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Leading with Values: Jessica McKellar, CEO and Founder of Pilot on Building Trust Through Personal Connection : Women in Tech San Francisco is an episode from Women in Tech Podcast, hosted by Espree Devora by WeAreTech.fm.

This episode is 00:45:53 long.

This episode was published on Apr 20, 2026.

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