Systems for Creatives with Amy Pearson

How A Simple Email Automation Ends Most W9 Headaches


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Your inbox shouldn’t implode with W-9 requests every December. We walk through a tiny, high‑leverage automation that sends clients your W9 at exactly the right moment and keeps that info easy to find all year. If you’ve ever re-sent W-9 forms in a week, this workflow will feel like a breath of fresh air.

First, set up a single source of truth: a shared Google Drive or Dropbox folder with your current, signed W9. 

Then plug that link into Dubsado’s “after contract signed” email so every new client automatically receives a clear, professional note with the download link. No extra clicks, no remembering to attach a file, no scrambling during tax season—just a simple system that works in the background while you focus on delivery.

Bonus tip: add a Zapier automation that tags or subscribes every booked client to a year-specific list. 

In November, send a quick reminder email to that list with the same W9 link so bookkeepers and ops teams can file it ahead of deadlines. 

One final step create a recurring December task inside your Project Management tool to refresh the W9, replace the file in the same folder, and use a year-stamped filename for instant clarity. The link never changes, the file stays current, and your onboarding stays tidy. (Mic drop!)

If you’re ready to reclaim your year-end, tune in, take the steps, and set it once. 

Like this kind of clean, quiet automation? Subscribe, share the episode with a freelancer friend, and leave a review telling us which workflow you want simplified next.

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Systems for Creatives with Amy PearsonBy Amy Pearson