Pilot
AI-assisted bookkeeping, tax and CFO services for US start-ups
Overview
Pilot provides bookkeeping, tax, CFO and outsourced-operations services to US start-ups and small businesses, with its in-house AI Accountant handling categorisation, reconciliation and month-end close. It was started in 2017 by Waseem Daher, Jeff Arnold and Jessica McKellar, who earlier sold Ksplice to Oracle and Zulip to Dropbox. Prices are published and scale with monthly expenses.
Pricing
Pricing shown for reference only. These figures reflect RECATOOLS research as of 12 Oct 2026 and may be out of date or incomplete. This is not financial or purchasing advice — always confirm the current price on the provider’s official website before making any decision.
- AI categorises transactions, reconciles accounts and closes monthly
- Standard chart of accounts; year-end package for your tax preparer
- Instant AI answers on past transactions and cash flow; in-app support
- US-based bookkeeper who handles, explains and reviews your books
- Cash or accrual basis; up to 10 vendor bills a month; custom chart of accounts
- Reports on the 10th business day; support in-app, by email and phone
- Keep your existing QuickBooks account and history
- Full AR and AP; payroll administration; reports on the 6th business day
- CFO advisory, financial planning and fundraising support
- Single-member LLC from $1,000/year (just formed: from $750)
- Partnerships and S-Corps from $2,000/year, including Delaware franchise tax
- C-Corps from $2,450/year, including Delaware franchise tax and up to 10 1099-NECs
- Basic $1,750/month: financial model, budget vs actuals, monthly CFO call
- Essentials $3,150/month: runway, investor and board reporting
- Custom from $5,250/month: 13-week cash flow, weekly CFO calls
- Starter $750 one-time: incorporation, banking and payroll setup
- Essentials from $850/month: HR, payroll and benefits, invoice collection, bill pay
- Custom: high-volume AR/AP, state payroll compliance, stock administration
Use cases
What you can produce with Pilot
- Monthly bookkeeping handed over: the AI Accountant categorises, reconciles and closes, and on Core a US-based bookkeeper reviews the books
- Plain-English answers from Pilot AI in the portal about spending and cash flow, plus hiring and cash-flow scenarios
- Federal and state income tax returns, Delaware franchise tax and 1099-NECs filed by Pilot, bought alongside bookkeeping
- The US R&D tax credit claimed against future payroll taxes, for 20% of the credit received
- Fractional CFO work: a financial model, budget versus actuals, runway planning and investor or board reporting
- Bill payment, invoice collection, payroll and HR administration outsourced on Pilot's operations plans
- Bank accounts, cards and tools such as Stripe and Gusto connected so transactions flow into the books
Pilot is a managed back office for US start-ups and small businesses: bookkeeping, tax filing, fractional CFO work and outsourced operations, delivered by Pilot staff on top of its own AI Accountant software. Essentials, at $99 a month, is AI-run cash-basis bookkeeping; Core adds a US-based bookkeeper and accrual books from $299 a month on annual billing; tax and CFO services are priced separately and published, which is rarer than it should be in this market.
It fits US-incorporated, venture-backed companies that want one accountable provider for books, taxes and investor reporting. It does not fit companies whose only entity is in ASEAN, because the service is built around US filings. Public reviews are thin and mixed, with complaints centred on tax-service communication.
What we found
Pilot is a US bookkeeping and tax provider for start-ups and small businesses that runs on its own software. The core service is unchanged: a Pilot team closes your books each month, prepares federal and state tax returns, and can add fractional CFO work, R&D tax-credit claims and outsourced operations. What has changed is how much of the close the software now does. Pilot's AI Accountant categorises transactions, reconciles accounts and flags duplicate charges or new vendors for review, and a portal assistant answers questions about past spending. In June 2026 the company launched Meridian, which sells the same close engine to other accounting firms; Pilot says the system has closed more than 187,000 months of books for over 8,000 businesses.
The price list is unusually open for this category. Essentials costs $99 a month for businesses with up to $100,000 in monthly expenses and covers cash-basis books closed largely by AI. Core adds a US-based bookkeeper, accrual accounting and reports by the tenth business day, starting at $299 a month on annual billing and rising with expenses; an earlier version of this page put Core at $499. Tax filing starts at $1,000 a year for a single-member LLC and $2,450 for a C-corp, sold only alongside bookkeeping, and CFO plans begin at $1,750 a month.
Public feedback is mixed. Trustpilot shows 2.9 out of 5 from only 20 reviews. One complaint, from May 2026, says the reviewer paid nearly $2,400 for tax work and received only an extension, and another describes weeks without replies from the tax team; positive reviews credit transparent onboarding.
Pilot fits US-incorporated companies, particularly venture-backed ones, that want bookkeeping, tax and CFO work from one provider. Every plan is built around US federal and state filings, so a company incorporated in Singapore, Malaysia or elsewhere in ASEAN will only find a fit for a US subsidiary.
Compiled by RECATOOLS from public sources: vendor documentation and pricing, code repositories and published reporting.
About this listing
This entry was compiled from publicly available data including Pilot's official website, press releases, documentation, and reputable third-party publications. RECATOOLS is not affiliated with Pilot unless explicitly stated.
Third-party AI tools update their pricing, features, availability, and policies frequently. Information here may be outdated by the time you read this — we make reasonable efforts to keep listings current, but cannot guarantee absolute accuracy.
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