Pilot.com, Inc.

Pilot.com, Inc. operates an outsourced financial back office for startups and small businesses, delivering bookkeeping, tax preparation, and CFO advisory services that pair dedicated human accountants with proprietary software for real-time reporting. The company was founded in 2017 by Waseem Daher, Jessica McKellar, and Jeff Arnold, three MIT-trained engineers who had previously built and sold two companies together. It is headquartered in San Francisco, with a second office in Nashville, Tennessee.

Pilot's platform automates transaction categorization and monthly close while assigning each client a finance team, targeting venture-backed technology companies, ecommerce sellers, and professional-services firms that outgrow entry-level tools. The founders previously created Ksplice, a Linux software-updating firm acquired by Oracle in 2011, and Zulip, a workplace chat product acquired by Dropbox in 2014; that track record helped Pilot attract early startup clients. The company has since expanded into R&D tax-credit filing and added AI-assisted bookkeeping features.

Pilot has raised roughly $222 million across six rounds from investors including Sequoia Capital, Index Ventures, Bezos Expeditions, Stripe, and Whale Rock Capital, alongside founders such as Patrick and John Collison and Drew Houston. A $100 million Series C in March 2021 valued the company at $1.2 billion. Pilot employs approximately 420 people as of 2026 and remains privately held.