Tailride

Tailride connects to your inbox and vendor portals to automatically pull invoices and receipts. The AI classifies them, matches them with your transactions, and you stop chasing every single PDF by hand.

The tool is built for accountants and founders juggling multiple clients in parallel. Instead of spending your evenings scanning emails and downloading invoices from Stripe, AWS, Google, Meta or LinkedIn, you plug your sources in once and Tailride runs on its own.

What Tailride does for you:

• Inbox scanning: detects invoices and receipts in Gmail and Outlook and extracts them with zero manual rules
• Vendor portals: automatically grabs PDFs from Stripe, AWS, Shopify and other SaaS
• AI processing: names, classifies and dates every document in the right folder
• Reconciliation: matches each invoice to the corresponding bank transaction
• Accounting integrations: pushes documents straight to your accounting tool

You save several hours a month on bookkeeping and your accountant finally has everything they need, without having to chase you. The tool is rated 4.09/5 by its users, and the free plan is enough to test it on one client before upgrading to Tailride.