Stanford Tech Club: Fireside with Jessica McKellar, Founder & CEO of Pilot

​As AI rapidly transforms enterprise software, the real question is not whether workflows can be automated, but which companies will build durable, trusted systems that last.

​Join us for an intimate fireside chat with Jessica, Founder and CEO of Pilot. Pilot is a category-defining platform modernizing back office financial operations for startups and growth-stage companies, backed by Sequoia’s Pat Grady and other top-tier investors.

​Jessica has spent her career building infrastructure that quietly powers modern work. She is the Founder and CEO of Pilot and previously served as the company’s Founder and CTO. Before Pilot, she was Director of Engineering at Dropbox, joining through the acquisition of Zulip, a group collaboration tool she co-founded and led as VP of Engineering. Earlier, she was an Engineering Manager at Oracle and a Software Engineer at Ksplice, which was acquired by Oracle for its technology enabling Linux systems to update without rebooting.

​In this conversation, we will explore how AI is reshaping financial operations and workflow software, and what it takes to build a defensible company in an era where core capabilities can commoditize quickly.

​We will cover:

​• What durable defensibility looks like in workflow software in the age of foundation models
• Where AI creates real operational leverage versus shallow automation
• How to build trust in systems that touch mission-critical financial data
• Product and go-to-market lessons from scaling a deeply operational platform
• How technical founders evolve from engineering leader to CEO

​Expect a candid discussion on long-term value creation, trust, and the next generation of enduring workflow platforms.

​Location: M109
Time: Friday, Feb 27, 12:00 PM – 1:00 PM
Speaker: Jessica McKellar, Founder and CEO, Pilot
Moderator: Catherine Li