Bookeeping AI

TL;DR

AI accountant “Paula” automates 95% of bookkeeping tasks.
Generates invoices, categorizes expenses & syncs bank data in seconds.
Ideal for freelancers, small businesses & finance teams wanting real-time insights.
Starts at $29/mo with free 7-day trial; no QuickBooks required.

What is Bookeeping AI

Bookeeping AI is an AI Accounting & Finance Automation platform that replaces traditional bookkeeping software and manual data entry with an intelligent assistant named Paula. The cloud-based tool connects to banks, payment processors and documents to automatically categorize transactions, generate invoices, reconcile receipts, produce real-time financial reports and provide tax compliance guidance, positioning it in the AI Bookkeeping & Accounting Assistant category.

Key Features

AI Financial Assistant (Paula) – Chat-based interface lets users request invoices, summaries or tax advice in natural language, saving hours of manual work.
Automated Bank & Stripe Sync – Connects to 5,000+ financial institutions to pull transactions and fees, ensuring books are always up to date.
Smart Invoicing & Payments – Generates branded invoices from a prompt, supports recurring billing and instant card payments via Stripe.
AI Receipt Matching – Scans emails or uploads, then automatically attaches receipts to the correct expense line item for perfect audit trails.
Real-Time AI Audit Score – Continuous review of books with proactive alerts and suggestions to fix discrepancies before they become issues.
E-Sign & Document Management – Creates, stores and obtains legally binding signatures on contracts, tax forms and other business docs.
Tax & Compliance Guidance – Pulls IRS resources and fills forms such as 1099 or W-2, reducing reliance on external accountants.

Who is Bookeeping AI for?

Freelancers & Solo Entrepreneurs needing automated invoicing and expense tracking.
Small- to Mid-Sized Business Owners looking to replace QuickBooks or spreadsheets.
E-commerce & SaaS Founders who require real-time P&L and Stripe fee reconciliation.
Finance & Accounting Teams seeking AI-driven transaction categorization and audit prep.
Agencies & Consultants managing multiple client invoices and cash-flow insights.

Key Use Cases & Applications

Automating monthly bookkeeping for a Shopify or Stripe-based store.
Generating and emailing invoices for consulting projects within seconds.
Categorizing and matching receipts to reduce audit preparation time.
Producing real-time cash-flow, P&L and balance-sheet reports for investors.
Filling and e-signing 1099 forms during tax season without external software.

Pros

Intuitive chat interface drastically lowers learning curve.
Unlimited transactions even on entry plan—rare among accounting tools.
Built-in AI audit and tax guidance reduce compliance risks.
Replaces multiple apps (invoicing, e-sign, storage) with one platform.

Cons

No direct payroll processing yet; users must integrate third-party services.
Advanced human support only on higher-tier plans.
Feature set may feel overwhelming for users seeking basic ledgers only.

Pricing Info

Start – $29.00/mo: Unlimited transactions & invoices, 2 bank connections, 2024 catch-up bookkeeping, 2 team seats, ChatGPT access, AI support, free 7-day trial.
Pro – $49.00/mo: Unlimited transactions & invoices, 4 bank connections, up to 3 years catch-up, 5 team seats, ChatGPT & Claude, AI + human support.
Scale – $79.00/mo: Unlimited transactions & invoices, 6 bank connections, up to 5 years catch-up, 10 team seats, unlimited ChatGPT & Claude, priority AI + human support.

FAQs

Is there a free trial available before subscribing?