Collect W-9s and get 1099s ready for contractors before January

The problem

In January, owners discover they never collected W-9s from the cleaner, web designer or subcontractors they paid during the year, then spend days chasing tax IDs and adding up payments to meet the 1099 deadline.

How AI solves it

Export a vendor payment report from your accounting software and ask an AI assistant to flag which vendors are likely contractors who need a 1099 (individuals and LLCs paid for services, not product suppliers or card-paid vendors), and which have no W-9 on file. Have it draft a short, friendly W-9 request email and a reminder, and a checklist for each vendor: legal name, tax classification, address and total paid. Collect W-9s through a secure e-sign or form tool rather than email, then file through your accounting software or an e-file service. Confirm the current reporting threshold and deadlines with your accountant, since rules changed for payments made in 2026.

Tools that do this

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• QuickBooks
• Jotform
• ChatGPT

What you can expect

Time saved: 4-8 hrs in January (estimate)
Cost saved: Avoid late-filing penalties and January scrambling (estimate)
Difficulty: Easy

Industry guides: AI for Retail Stores & Boutiques · AI for Accountants, Bookkeepers & Tax Pros · AI for Property Managers & Landlords

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