Freedom251 › AI Accounting Software
Pilot
by Pilot
Plans
| Plan | Billed and limits | Price |
|---|---|---|
| Essentials | billed monthly · Up to $100,000 in monthly expenses | $99 a month |
| Core | billed annually · $0 in monthly expenses · Up to 10 vendor bills per month | Free |
| Custom | Complex business structures · Custom workflows and reporting · Full accounts receivable · Full accounts payable · Payroll administration · CFO advisory | On request |
| Basic (CFO) | billed annually · Custom financial model · Budget-versus-actual analysis · Scenario planning · KPI dashboard · Monthly CFO call | $1,750 a month |
| Essentials (tax) | billed annually · Federal, state, and city income tax filing · Delaware franchise tax filing · Up to 10 1099-NEC filings · Must be purchased with Pilot Bookkeeping | $2,450 a year |
| Essentials (CFO) | billed annually · Everything in Basic · Cash and runway optimization · Investor and board reporting · Fundraising and M&A support · Biweekly CFO call | $3,150 a month |
| Standard (tax) | billed annually · Federal and state corporate income tax filing · Delaware franchise tax filing · Up to 25 1099-NEC filings · Must be purchased with Pilot Bookkeeping | $5,400 a year |
| Starter (tax) | billed annually · Federal and state corporate income tax filing · Delaware franchise tax filing · Must be purchased with Pilot Bookkeeping | $750 a year |
The first 8 of 11 plans, as pilot.com lists them, read 20 Sept 2026. The maker's own page has the final word. Every plan
Facts from Pilot's own pages
- Accountant access
- Yes · pilot.com, 20 Sept 2026
- Accounting-service limitation
- Pilot says it does not provide audits, assurance, public-accounting services, or certifications of GAAP compliance. · pilot.com, 21 Oct 2026
- AI transaction categorization
- Pilot’s AI Accountant categorizes transactions and reconciles accounts as activity comes in. · pilot.com, 21 Oct 2026
- Anomaly flags
- Pilot says its AI Accountant flags unusual items such as duplicate charges, unexpected amounts, and new vendors. · pilot.com, 21 Oct 2026
- API connections
- Pilot says it uses secure API connections and bank-level authentication to connect financial and business tools. · pilot.com, 21 Oct 2026
- Ask questions about finances
- Pilot AI in the customer portal accepts plain-English questions about company financials and returns answers. · pilot.com, 21 Oct 2026
- Automated reconciliation
- Yes · pilot.com, 20 Sept 2026
- Bank feeds
- Yes · pilot.com, 20 Sept 2026
- Bookkeeping requirements
- Pilot says it requires electronic transaction access, expense-reporting software, and separation of business and personal expenses. · pilot.com, 21 Oct 2026
- Cash-flow scenarios
- Pilot says its tools let customers model cash-flow scenarios, including whether they can afford new hires. · pilot.com, 21 Oct 2026
- CFO advisory
- Pilot CFO services cover runway, margins, financial planning, fundraising, and strategic decisions. · pilot.com, 21 Oct 2026
- Company size and status
- LinkedIn lists Pilot as privately held with 201–500 employees. · linkedin.com, 21 Oct 2026
- Documentation depth
- Pilot’s FAQ covers pricing, support, bookkeeping, tax, and R&D credits; the opened pages did not identify developer documentation or system requirements. · pilot.com, 21 Oct 2026
- Expense tracking
- The homepage says customers can track company expenses in real time. · pilot.com, 21 Oct 2026
- Founded
- LinkedIn lists Pilot’s founding year as 2016. · linkedin.com, 21 Oct 2026
- Free plan
- Yes · pilot.com, 20 Sept 2026
- Funding
- Pilot’s About page says it has raised more than $150 million from investors including Sequoia, Index Ventures, Stripe, Bezos Expeditions, and Whale Rock. · pilot.com, 21 Oct 2026
- Headquarters
- San Francisco, California, and Nashville, Tennessee, United States · pilot.com, 28 Sept 2026
- Integration constraints
- Pilot says it primarily supports US-based banks and payment platforms, while naming Wise, Deel, and Remote.com as international examples. · pilot.com, 21 Oct 2026
- Integrations
- Pilot says it connects with more than 10,000 banks, payment processors, payroll systems, and business tools. · pilot.com, 21 Oct 2026
- Inventory tracking
- No · pilot.com, 20 Sept 2026
- License and hosting
- Pilot’s privacy policy describes SaaS tools; the opened pages do not name an open-source license or describe self-hosting. · pilot.com, 21 Oct 2026
- Limit: bank connectivity
- A Trustpilot reviewer reported repeated connection failures, sync errors, missing transactions, and manual cleanup. · trustpilot.com, 21 Oct 2026
- Limit: perceived product value
- A Trustpilot reviewer said the platform provided little financial insight and characterized it as a thin layer over QuickBooks and Plaid. · trustpilot.com, 21 Oct 2026
Where Pilot stands on Freedom251
- AI Accounting Software#7 of 32
- Bookkeeping Software#21 of 75