Pilot came directly out of the pain the three founders felt doing their own books at their first two companies, Ksplice (acquired by Oracle) and Zulip (acquired by Dropbox). During the Ksplice acquisition, Oracle's own finance team noticed the internal bookkeeping tooling the founders had built for themselves and told them it should have been their actual product; that comment, combined with their own first-hand frustration, is what they credit with planting the idea for Pilot.

“we experienced the pain points of bookkeeping first-hand”

Pilot's very first users were friends of the three founders. Jeff and Waseem called them directly and signed them up as paying bookkeeping clients while doing the books by hand in QuickBooks, before the automation software existed.

“We called up all our friends, signed a few as clients, and got to work.”

Jeff and Waseem directly called friends and signed them up as Pilot's first paying bookkeeping clients, doing the books themselves by hand in QuickBooks while Jessica built the software.

“We called up all our friends, signed a few as clients, and got to work.”