Pilot was the third company for the same three MIT friends: Jessica McKellar, Jeff Arnold, and Waseem Daher. Their first company, Ksplice, was acquired by Oracle. Their second, Zulip, was acquired by Dropbox.

The Oracle Moment

During the Ksplice acquisition, Oracle's finance team noticed the bookkeeping software the founders had built internally. They said: "Oracle is the most sophisticated financial technology company in the world. We don't have anything like this. Why are you even doing your company? This should have been your product."

Starting with Pain

In early 2017, the founders decided to tackle bookkeeping. "Bookkeeping isn't sexy. But we experienced the pain points first-hand."

Founders Doing the Work

The early company was Jeff and Waseem doing their clients' bookkeeping by hand in QuickBooks while Jessica built the tech. "We called up all our friends, signed a few as clients, and got to work."

They time-tracked everything and prioritized automation based on: how error-prone a task was and how long it took.

The Insight

"What's really good at taking highly structured data and robustly transforming it according to well-defined rules? The answer is definitely not a person." Their software does repetitive work so humans can focus on high-value client support.

Growth

Pilot raised over $160M in funding and became the largest startup-focused bookkeeping firm in the US, valued at $1.2B.

• Previous exits: 2 (Oracle, Dropbox)
• Total raised: $160M+
• Valuation: $1.2B
• Model: Expert bookkeepers + software automation