In episode 177 of The Woodard Report Podcast, Joe Woodard sits down with Jessica McKellar, CEO and co-founder of Pilot, to discuss how technology is reshaping bookkeeping and accounting. From her beginnings as a computer science student at MIT to leading a company that serves thousands of businesses, Jessica shares how Pilot was built around a simple but powerful conviction: small business owners shouldn't have to be their own bookkeeper, accountant, and financial advisor all at once.
Jessica never set out to build a bookkeeping company. A graduate of MIT with a degree in computer science, she spent her early career building technology startups alongside her longtime co-founder, Waseem Daher.
The inspiration for Pilot came from a problem they experienced firsthand while building their own businesses. “So we literally bought a copy of QuickBooks for Dummies and bought a copy of QuickBooks desktop. And we did the books ourselves.”
As first-time founders, they found themselves responsible for bookkeeping, taxes, and financial operations without any accounting background. After experiencing the same challenge across multiple ventures, they began asking a bigger question: How could technology make financial back-office work easier and more scalable for small businesses?
When Pilot launched in 2017, the goal was not to create another general ledger platform. Instead, Jessica and her team focused on automating bookkeeping workflows while continuing to serve clients directly. “The way that you know that you build the right software is you serve customers.”
Jessica describes how Pilot's earliest days involved her co-founder manually performing bookkeeping work in QuickBooks Online while she simultaneously built software to automate repetitive tasks. By solving real client problems first, the company was able to develop tools grounded in actual accounting workflows.
Over the last several years, Pilot has grown to serve more than 4,000 clients. According to Jessica, that growth was only possible because technology allowed the company to scale differently than traditional service organizations.
“The world that we live in today is a world where a comparatively small team is able to steward a comparatively large portfolio because the work is largely executed in software.”
Joe notes that many accounting firms are watching developments like Pilot's with equal parts curiosity and caution. The question often becomes whether automation companies are competitors or collaborators.
Jessica explains that her broader mission is to ensure small business owners have access to high-quality financial support. “My goal in this world is that every small business owner has access to high-quality finance and accounting support.”
Rather than viewing technology as a replacement for accounting professionals, she sees it as a tool that can help firms serve more clients more effectively. “I want every accounting firm in the United States to have access to that platform if they want it.”
Her vision centers on giving firms access to technology that increases efficiency while improving the client experience.
One of the most thought-provoking moments of the conversation comes when Jessica argues that the traditional economics of accounting services are undergoing a fundamental shift.
According to Jessica, automation is changing the relationship between effort and value. As technology handles more routine tasks, firms must rethink how they structure services, deliver value, and build sustainable business models.
She points to Pilot's ability to generate significant revenue per accounting professional as evidence that new operating models are emerging. The challenge for firms is not simply adopting new software. It is rethinking the underlying assumptions about how accounting work gets done.
As artificial intelligence and automation continue advancing, the accounting profession faces both opportunity and disruption. Jessica believes the firms that thrive will be those that embrace technology as a force multiplier rather than a threat.
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This article was written with the assistance of AI and edited by a human.