Founders and Funders: Sarah Ahmad and Jessica McKellar - Women Founders & CEOs in Conversation
Join us for an evening of candid insight and real-world wisdom with Jessica McKellar, CEO & Co-founder of Pilot, and Sarah Ahmad, CEO & Co-founder of Stable. Presented by Pilot and Stable, this Founders & Funders Night brings together founders, funders, and operators for an honest conversation about what it really takes to build, scale, and sustain companies in today’s startup ecosystem. Hosted by Diana Nicholas, former Founder and current leader at Pilot, this event dives deep into the realities of leadership, resilience, and growth in the modern startup landscape.
We’ll explore:
The Founder’s Journey: What it truly takes to lead through early-stage chaos, growth plateaus, and market shifts
Building with Intention: Lessons in scaling teams, culture, and customer trust
Navigating Capital: How to build lasting investor relationships and decide when — or whether — to raise
Women Who Build: What it means to lead as a woman founder and CEO in today’s tech landscape
The Future of Founding: Where innovation, discipline, and authenticity intersect in modern entrepreneurship
Whether you’re a founder building your next venture, an investor seeking fresh perspective, or simply inspired by women who lead with clarity and conviction, this conversation will offer practical insights and unfiltered wisdom.
Come for the honest founder stories, stay for the lively discussion, drinks, and great company.
About Sarah Ahmad:
Sarah Ahmad is the co-founder and CEO of Stable. An alumna of Northwestern University and Y Combinator with a background in integrated engineering and economics, Sarah previously worked as a UX engineer at LifeLink. Since co-founding the company in 2019, Ahmad has led the development of Stable into a solution trusted by over 10,000 companies, from early-stage startups to enterprise organizations like DoorDash and GitLab.
About Jessica McKellar:
Jessica McKellar is the CEO and co-founder of Pilot, the leading provider of accounting, tax, and CFO services for startups and small businesses. Jessica is an MIT-trained computer scientist who has founded multiple companies and led two through acquisitions, by Oracle and Dropbox. Fun fact: she was a technical advisor to the HBO show Silicon Valley.
About Pilot:
Pilot provides expert bookkeeping, tax, and CFO services tailored to startups and small businesses. Headquartered in San Francisco and Nashville, Pilot combines U.S.-based finance experts with powerful software to deliver trustworthy financials and actionable insights — helping founders focus on what they do best: building their businesses.
About Stable:
Stable frees businesses to move forward faster with an AI-powered virtual mailbox. From the Stable platform, businesses can secure a permanent business address, act on mail, and use AI summaries, automated mail routing, data extraction, and more to automate mail-driven workflows. Stable empowers businesses of all sizes to eliminate back-office friction and focus on growth.