The Woodard Report Podcast · 2026-06-24 · 30 min
On this episode of the Woodard Report podcast, Joe speaks with Jessica McKellar about her journey from studying computer science at MIT and building successful software startups to founding Pilot, a bookkeeping and accounting technology company. Jessica shares how Pilot evolved from solving the financial back-office challenges faced by entrepreneurs into a platform and explains how automation, AI, and value-based pricing are reshaping the economics of accounting firms. She also introduces Meridian, Pilot's new platform that enables autonomous bookkeeping, month-end close processes, and AI-assisted accounting workflows designed to help firms scale while improving both client and employee experiences. About Jessica McKellar Jessica McKellar is the co-founder and CEO of Pilot. She started the company with a simple conviction: small business owners shouldn't have to be their own bookkeeper, accountant, and financial advisor all at once. Today, Pilot serves more than 3,500 businesses, from neighborhood restaurants and retail shops to growing service businesses, helping owners get books off their plates so they can focus on what actually grows their company.
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