Startup
Pilot
Bookkeeping, tax and CFO services for US startups and small businesses, run by an AI Accountant with a US-based finance team.
| Founded | 2017, San Francisco; second office in Nashville |
|---|---|
| Founders | Jessica McKellar (founder and CEO), Waseem Daher, Jeff Arnold |
| Stage | Series C |
| Total funding | More than US$150m across Series A, B and C |
| Last round | Series C, 2021: US$60m led by Sequoia Capital, expanded to US$100m with Bezos Expeditions and Whale Rock Capital at a US$1.2bn valuation |
| Earlier rounds | Series A, US$15m, led by Index Ventures; investors include Patrick and John Collison, Drew Houston and Diane Greene; Stripe is also an investor |
| What it does | Monthly bookkeeping, business tax filing, R&D tax credit claims, CFO services, outsourced operations and stock administration. Its AI Accountant runs bookkeeping from onboarding to monthly close |
| Recent moves | Launched the AI Accountant; a Local Partner Program that gives independent bookkeepers its platform and refers clients to them; and Meridian, which sells its month-end close automation to accounting firms |
| Traction | 3,500+ startups and small businesses as customers; bookkeeping for more than 7,000 businesses over its history and 187,000 closes |
| Pricing | Bookkeeping: Essentials US$99 a month; Core from US$299 a month billed annually; Custom on quote. Tax from US$1,000 a year (single-member LLC) to US$2,450 a year (C corp); CFO services from US$1,750 a month; R&D credit fee 20% of the credit |
| Markets | US |
| Peers | Digits, Fondo, Kruze Consulting, Collective, Truewind, Finaloop |
Why it matters
Pilot has kept the books for more than 7,000 US businesses and was valued at US$1.2bn in 2021 with backing from Sequoia, Index Ventures, Stripe and Bezos Expeditions. Its AI Accountant and Meridian show a services firm turning its own automation into software for other accounting firms.
Updated October 2026.
Part of Accountio’s accounting technology coverage.
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