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What is Pilot?
Founded in 2017 and headquartered in San Francisco, Pilot combines finance software with accounting experts for startups and small businesses. The company says it has raised more than $150 million and serves 3,000+ companies.
Pilot is a managed bookkeeping and tax service rather than a do-it-yourself ledger. Customers connect banks, cards, payroll, payment processors, and other tools; Pilot’s software imports and categorizes transactions, while its finance team reviews the books, reconciles accounts, closes monthly reporting, and answers questions in the Pilot Portal. Essentials combines AI-assisted bookkeeping with human support, while Core adds a dedicated US-based bookkeeper.
The platform covers cash- or accrual-basis bookkeeping, financial statements, tax preparation, 1099 filing, Delaware franchise tax, CFO advisory, and selected back-office work. Essentials is AI-assisted bookkeeping with human support, while Core adds dedicated bookkeeping and broader data sources. Pilot Tax is separate from bookkeeping, must be purchased with bookkeeping, and does not include personal income-tax filing; complex entities, extra states, and international activity can add scope and cost.
Pilot is aimed at US startups, small businesses, and growing companies that want outsourced books instead of managing QuickBooks themselves. Essentials starts at $99 per month, while Core is custom-priced based on monthly expenses and service requirements; tax starts at $1,000 per year for a single-member LLC. Essentials is sold monthly, while Core and other services use annual or custom pricing depending on the plan.
Key features
Managed bookkeeping
Pilot categorizes transactions, reconciles accounts, and closes books monthly using connected financial data and human review.
Cash or accrual books
Core supports cash- or accrual-basis bookkeeping across banks, cards, payroll, AP, inventory, and payment platforms.
Business tax filing
Pilot Tax covers federal and state income-tax filing, selected city filings, Delaware franchise tax, and included 1099-NEC filings.
Financial reporting
Customers receive financial statements and can ask questions about transactions, cash flow, and operating scenarios.
CFO advisory
CFO plans provide financial models, runway analysis, investor and board reporting, and strategic projects.
Back-office support
Higher-tier services can include bill payment, invoice collection, payroll administration, and custom workflows.
AI-assisted answers
Pilot AI provides instant answers about past transactions and current cash flow while the human team handles review and support.
Pilot pricing
Essentials starts at $99 per month for businesses with up to $100,000 in monthly expenses. Core is custom-priced, with pricing varying according to monthly expenses, connected institutions, bills, invoices, and support needs; Pilot Tax starts at $1,000 per year for a single-member LLC and must be purchased with bookkeeping. Essentials is monthly, while Core and other services may use annual or custom billing.
| Plan | Price | What's included |
|---|---|---|
| Essentials | $99/monthUp to $100,000 in monthly expenses | AI-assisted cash-basis bookkeeping, bank and credit-card data, standard chart of accounts, year-end tax package, Pilot AI answers, and human support. |
| Core | CustomPricing varies with monthly expenses | Everything in Essentials plus a dedicated US-based bookkeeper, cash or accrual books, broader integrations, custom chart of accounts, and phone, email, and in-app support. |
| Custom | Custom | Complex structures, historical QuickBooks data, custom workflows, reporting, accounts receivable, accounts payable, payroll administration, and optional CFO support. |
| Pilot Tax | From $1,000/yearSingle-member LLC; bookkeeping required | Federal and state filing, free extension, quarterly safe-harbor payments, Schedule C, and specified income-source reporting. |
| CFO Basic | $1,750/month | Custom financial model, strategic insights, and industry-specific KPI dashboard. |
Free trial: No free trial is advertised; an onboarding charge equal to one month of bookkeeping applies under Pilot’s FAQ.
Pros & cons
Pros
- Combines automated transaction processing with human support and review.
- Offers bookkeeping, tax preparation, CFO services, and selected back-office work in one provider.
- Connects to a broad set of banks, payroll systems, payment processors, and business tools.
- Core supports accrual accounting and more complex data sources than Essentials.
Cons
- Pilot Tax is not included in bookkeeping and must be purchased with Pilot Bookkeeping.
- Pilot does not currently file personal income taxes.
- Pricing can rise with expenses, institutions, bills, invoices, and support needs.
- Core pricing is custom rather than publicly listed as a fixed monthly rate.
Who is Pilot best for?
- US startups that want a finance team without hiring an in-house bookkeeper.
- Small businesses needing monthly books plus a tax-ready year-end package.
- Growing companies that need cash-flow visibility and optional CFO guidance.
- Founders whose bank, payroll, and payment data already lives in connected cloud tools.
Coverage
Integrations
Notable customers
Frequently asked questions
What is Pilot’s lowest price?
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Pilot’s current bookkeeping pricing page lists Essentials at $99 per month for businesses with up to $100,000 in monthly expenses. Core is custom-priced, while single-member LLC tax starts at $1,000 per year.
How does Pilot bookkeeping work, and how long does it take?
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Customers connect financial accounts and business tools, then Pilot imports, categorizes, reconciles, and closes the books monthly. The company says Portal questions typically receive a response within one business day; completion timing depends on connected data and customer responses.
How does Pilot compare with Bench?
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Pilot starts at $99 per month for Essentials and offers AI-assisted bookkeeping with human support, while Bench’s current public entry price is $199 per month for Bookkeeping Grow. Both combine software with human bookkeepers, but Pilot also offers tax filing, CFO advisory, and broader finance operations as add-ons.
What integrations does Pilot support?
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Pilot says it connects to more than 10,000 banks, payroll systems, payment processors, and business tools. Named examples include Mercury, Stripe, Gusto, Ramp, Shopify, Wise, Deel, and QuickBooks-related systems.
Who is Pilot for?
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Pilot is designed for US startups, small businesses, and growing companies that want outsourced books and optional tax or CFO help. It is less suitable for owners seeking a purely self-serve ledger or personal tax filing.
Is Pilot secure and accurate, and is it human or AI bookkeeping?
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Pilot uses secure API connections and bank-level authentication, and its Portal says financial information and communications are encrypted. Essentials combines AI-assisted bookkeeping with human support, while Core adds a dedicated US-based bookkeeper for ongoing review.
Sources
Facts and pricing verified on October 19, 2026. Vendors change pricing often, so confirm with Pilot before buying. How we research
