AI bookkeeper · Daily close · Import from Pilot · Free Plan
Pilot pairs software with a human finance team and charges a monthly retainer that runs into the hundreds, billed higher as your expenses grow. HelloBooks is the AI-first alternative: an AI bookkeeper does the categorizing, reconciling, and closing your Pilot team does — every day, inside an account you own.
Import your Pilot data, run AI cleanup on any period that needs it, and move to software you control — Free Plan for early-stage founders, Pro at a $9.99/mo founding-member price (then $19.99) with unlimited users, AI included. Keep your CPA in the loop with reviewer mode.
1. AI does the work daily — not a monthly retainer
Pilot is a managed service: a human finance team categorizes and closes your books once a month for a retainer that runs into the hundreds. HelloBooks runs an AI bookkeeper on your bank feed every day — categorizing at 95%+ accuracy, matching transfers, reconciling accounts, and drafting month-end journal entries. You get close-ready books continuously, at a fraction of a managed-service retainer.
2. You own your books — it is software, not a service
With Pilot your books live inside a service engagement staffed by an assigned team. HelloBooks is software you control: your ledger lives in your account, you export any time, and the AI agent runs on a public MCP server you can query from Claude or ChatGPT. No engagement to renew, no team to be reassigned, no service you can be locked out of.
3. Software pricing, not startup-priced retainers
Pilot is priced for funded startups — a monthly retainer, billed higher as your expenses grow, with tax and CFO work as paid add-ons. HelloBooks Pro is a $9.99/mo founding-member price (then $19.99) with unlimited users, and the Free Plan covers most early-stage founders and solo LLCs at $0 — with AI included on every plan.
4. AI cleanup for the catch-up
Behind on the books, or moving mid-year off a service? Point the AI cleanup mode at the backlog — it backfills categorization, matches transfers, surfaces duplicates, and reopens the books in an afternoon. What catch-up bookkeeping firms charge $1,500–$5,000 for, without onboarding onto another retainer.
5. US compliance + your accountant, built in
IRS-ready books, 1099 e-file, and 50-state sales tax generated from the same ledger — plus a reviewer mode so your CPA reviews and signs without a separate subscription. You keep the human oversight Pilot sells, but as an option you control instead of a retainer you rent.
The differences that matter most when you replace a managed bookkeeping service with AI you own. For the full side-by-side, see the detailed HelloBooks vs Pilot comparison.
| Feature | HelloBooks | Pilot |
|---|---|---|
| Model | AI bookkeeping software you own + optional CPA review | Managed human + software bookkeeping service (retainer) |
| Cadence | Daily — books stay close-ready continuously | Monthly close, delivered after the month-end |
| Who does categorization | AI agent at 95%+ accuracy, learns your patterns | An assigned finance team / bookkeeper |
| Data ownership | Your account, export any time, open MCP access | Inside the service engagement |
| Starting price | Free Plan + Pro at $9.99/mo founding price (then $19.99), unlimited users | Monthly service retainer (hundreds/mo), scales with expenses |
| Catch-up / cleanup | AI cleanup mode included — backfills a stalled year in an afternoon | Historical/catch-up billed as an add-on |
| Bank connections | 11,000+ US banks via Plaid + AI statement upload | Connected on your behalf by the service |
| US tax filing | 1099 e-file + 50-state sales tax from the ledger | Tax & CFO as paid add-ons |
| Accountant access | Built-in reviewer mode + CPA practice dashboard | You rely on the assigned team |
| Open AI integration | MCP server — works in Claude, ChatGPT, any MCP client | None — closed service |
| Multi-entity | Built in, every plan | Separate engagement per entity |
Pilot is built for funded startups and priced like it — a monthly retainer that climbs with your expenses. If you are bootstrapped, pre-revenue, or just watching burn, HelloBooks gives you the same daily bookkeeping from an AI agent on a Free Plan or a $9.99/mo founding price.
Categorizing transactions and reconciling accounts is the exact work AI now does well. HelloBooks does the categorization and reconciliation automatically and keeps your CPA in the loop for the judgment calls — at a fraction of a managed-service retainer.
Pilot delivers your books after the month closes. HelloBooks keeps them reconciled daily, so you always know where you stand — and month-end is a 15-minute review instead of waiting on a service to deliver.
With Pilot your books live inside a service engagement. HelloBooks puts the ledger in your account with export any time and open MCP access, so your financials are yours — queryable from Claude, ChatGPT, or any MCP-aware client.
Pilot bills tax, CFO, and catch-up as separate add-ons that stack on the retainer. HelloBooks includes AI bookkeeping, US tax filing, cleanup, and multi-entity on every plan — so the price you see is the price you pay as you grow.
Moving off a managed service is simpler than it sounds — you bring your data in, the AI backfills anything open, and you own everything from there.
Step 1
Sign up free
Create your HelloBooks account at no cost — the Free Plan includes 5,000 AI credits and full reporting, no credit card.
Step 2
Import your Pilot data
Bring in your Pilot export / CSV — chart of accounts, historical transactions, and balances flow into your new ledger.
Step 3
Connect your bank
Link your bank via Plaid for live feeds across 11,000+ US banks. AI statement upload covers anything Plaid misses so nothing is lost in the switch.
Step 4
Run AI cleanup
Point the AI agent at any stalled or uncategorized period. It backfills categorization, matches transfers, surfaces duplicates, and reopens the books.
Step 5
Own it going forward
The AI runs daily from here — categorize, reconcile, close. Add your CPA in reviewer mode for oversight. Your books, in your account, on autopilot.
Free Plan with 5,000 AI credits, full reporting, and bank connection. No credit card. Import your Pilot data and let the AI keep the books current — then own your books going forward, without a monthly retainer.