Automate Sending Your W-9 (and Save Yourself from Year-End Chaos)

You know that moment in December when your inbox fills up with “Hey, can you send me your W-9 again?” emails?
Yeah — same.

If you’re a creative entrepreneur or freelancer working with multiple clients, this small but mighty automation will save you from that annual headache. It’s one of my favorite examples of a “set it and forget it” system that quietly takes care of business — no scrambling, no searching, no re-sending the same form over and over.

Here’s What I’m Talking About

• Why automating your W-9 matters
• How to set up your W-9 folder in Google Drive
• How to add your W-9 to your Dubsado canned email
• Bonus: Use Zapier to streamline your year-end follow-ups
• Keeping your W-9 updated automatically

Rather Listen To This Post?

Prefer to hear me talk through this step-by-step? You can listen to the full podcast episode right here:

Why Automate Your W-9

Let’s be honest — there’s enough chaos at the end of the year without having to re-send your tax form to every client you’ve ever worked with.

Automating this one simple step communicates “I’ve got my business together” energy while saving you a ton of time. It’s professional, easy, and helps your clients, too.

Here’s how to set it up in just a few minutes.

Step 1: Create Your W-9 Folder

Set up a folder in Google Drive (or Dropbox) and change the settings so that anyone with the link can access it. Complete your current W-9, name it something like “W9-2025,” and upload it to that folder.

Step 2: Add the Link to Your Dubsado Canned Email

In Dubsado, go to your Canned Emails section and open the “After Contract is Signed” email.
Add a short line that says something like:

“Here’s a copy of my W-9! Feel free to download and save it with your bookkeeping files for tax season.”

Then hyperlink your Google Drive folder. Done!

This way, every time a client signs a contract, your W-9 automatically goes out with their paperwork — no manual effort required.

Step 3: Add a Year-End Email (Optional but Smart)

Here’s a pro tip: keep a list of your clients for the year (for example, “2025 Clients”).
You can use Zapier to automatically add new clients to that list as they book.

Then, every October or November, send them an email that says something like:

“As we head into year-end, here’s my updated W-9 for your records. I know we’re all wrapping up books and prepping for tax season, so feel free to download this and save it with your files.”

Between the Dubsado automation and this reminder email, you’ll eliminate 99% of those W-9 requests before they ever hit your inbox.

Step 4: Add a Recurring Task

At the start of each December, create a repeating task in your project management tool that reminds you to update your W-9 for the new year.

Just download the latest form, fill it out, sign it with the upcoming year’s date, and upload it to your folder as “W9-2026.”

And that’s it — your system is refreshed and ready to go for another year of smooth, professional operations.

Want Help Setting This Up?

This quick five-minute system can save you hours every December. But if you’d rather have a pro walk you through automating not just your W-9s but all your client admin tasks, book a Systems Strategy Session with me.

In your session, we’ll find the hidden time-wasters in your workflow and turn them into smart systems that run on autopilot.
👉 Book your session here.

Conclusion

A well-run business isn’t just about the big things like workflows and onboarding — it’s about these tiny details that make everything feel seamless and stress-free.

By automating your W-9 delivery, you’re saving time, creating consistency, and showing clients that you’re organized and professional — all without lifting a finger.

Remember: every W-9 you don’t have to send manually is one more moment you get back in your day.

So go ahead — set this up today, and thank yourself when December rolls around.