Pilot Software, Inc.

About Pilot Software, Inc.

The story of Pilot starts with a problem every founder knows: bookkeeping. Waseem Daher, Jeff Arnold, and Jessica McKellar, three MIT computer club members, felt this pain firsthand through two previous startups. After selling their first company, Ksplice, to Oracle and their second, Zulip, to Dropbox, they decided to tackle the problem they wished someone had solved for them. In 2017, they founded Pilot to automate back-office tasks like bookkeeping, tax, and CFO services, aiming to give startups 'big-company superpowers'. Pilot’s approach combines smart software with human expertise, offering a service rather than just a tool. This model resonated with the startup community, attracting over 1,000 customers within a few years. The company provides financial reports, tax-ready statements, and strategic advice, allowing founders to focus on their actual business. A significant milestone came in January 2021, when Pilot announced a $60 million Series C funding round led by Sequoia Capital, which doubled its total funding to $120 million. Just a few months later, in March 2021, the company raised another $100 million, with investors including Jeff Bezos's firm, Bezos Expeditions, pushing its valuation to $1.2 billion and cementing its unicorn status.