OPS-Automate Blog
The 1099 Season Checklist That Starts in October, Not January
Every January, the same scramble: hundreds of vendors across dozens of client files, missing W-9s, payments split between checks and Venmo, and a filing deadline that doesn't move. The firms that survive 1099 season calmly are the ones that treat it as a Q4 project. Here's the checklist.
October — build the universe
1. Pull the vendor payment report for every client
All vendors paid $600+ year-to-date, by payment method. Card and third-party network payments (Stripe, PayPal) are the processor's 1099-K problem, not your 1099-NEC — flag them out early.
2. Clean the vendor lists first
Merge duplicates before you count anything. "John Smith," "Smith, John," and "J Smith Consulting" as three vendors means three wrong totals and one angry contractor.
3. Classify each vendor
Corporation, LLC taxed as what, individual, attorney (attorneys get 1099s regardless of entity type). Mark exempt vendors so nobody re-litigates them in January.
November — collect what's missing
4. Send W-9 requests in one batch
One professional request per client's vendor list, with a deadline and a follow-up schedule. Vendors respond in November; they disappear in January.
5. Start backup-withholding conversations early
Vendors who won't return a W-9 need to hear about 24% backup withholding while there are still payments left in the year to withhold from.
6. TIN-match what you have
Run IRS TIN matching on collected W-9s now. A mismatch discovered in November is a phone call; in January it's a B-notice.
December — reconcile the numbers
7. Tie payment totals to the ledger
The 1099 report should reconcile to the expense accounts. Unexplained gaps usually mean miscoded payments or an owner paying vendors from a personal account — find out now.
8. Handle the odd cases
Rents (1099-MISC box 1), attorney settlements, direct sales, deceased vendor estates. List them per client with the treatment decided and noted.
9. Confirm filing method and state requirements
IRIS or your filing software, plus each state's direct-filing rules. States are where January surprises live.
January — execute, don't discover
10. Generate, review, file
Forms generated from clean data need review, not research. Recipient copies out by Jan 31; federal e-file per deadline; state filings per your December list.
11. Log corrections as they surface
A tracked corrections list beats ad-hoc fixes — and shows the client the process worked.
The staffing angle
Notice what steps 1–9 have in common: they're systematic data work spread across October–December, exactly when firms have the most capacity and the least appetite for it. This is the classic assignment for a dedicated offshore junior accountant — one person works the checklist across your whole client base with daily KPI reporting, and your team enters January reviewing clean output instead of hunting W-9s. At a flat $950/month, the seat costs less than the write-offs from one badly-run 1099 season.
Put a $950/month junior accountant on your team
Full-time, dedicated, QA-checked daily, Time Doctor-tracked — with no upfront payment. Your first invoice arrives after 30 days, and you pay only if you're satisfied.
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