Behind the Screens: Automating Contractor Pay (So No One Has to Email 300 PDFs Again)

Paying people should be simple. But when you’ve got over 300 contractors and a system that involves manually creating, attaching, and emailing individual PDFs every week… it’s not. It’s a time-sucking, error-prone mess.

I found that out firsthand when I stepped in to help cover for someone on our finance team while they were out. That week turned into one of those “Okay, why are we still doing it this way?” moments that sparked one of my favorite automation projects so far.

Here’s how it worked before: the finance team had a Google Sheet with every contractor’s pay info. From there, someone had to copy each person’s details into a PDF, then attach it to a new email, write a message, and send it. Then repeat that. Three hundred times.

Not only did it take forever, but it opened the door to all kinds of mistakes. Sending the wrong PDF to the wrong person? Big yikes.

The Fix: Automate the Whole Thing with Google Apps Script

I knew we could do better. So I built a script using Google Apps Script that did everything for us automatically.

Each week, it pulls data from the spreadsheet, creates a personalized PDF for each contractor, and emails it directly to them. The message is customized, the file is clean, and the whole thing runs in just a few minutes.

No more copy-paste. No more 5-hour paydays. Just one click and done.

The Results: More Time, Fewer Errors, Happy Finance Team

Once the automation was live, we cut the weekly task down from hours to minutes. That freed up time for the finance team to focus on actual strategic work, not tedious admin. And with the script handling everything, we got rid of the risk of sending someone the wrong info.

It was one of those quiet wins that just made everyone’s life easier.

A Bit of Reflection (Because I’m That Kind of Nerd)

This wasn’t just a “cool automation” moment, it was a reminder of how important it is to question systems that feel clunky. Just because “we’ve always done it this way” doesn’t mean we should keep doing it that way.

Sometimes, the best innovations come from the simple act of noticing what’s broken and deciding to fix it.

Thinking About Automating Something Too?

If you’re stuck doing a repetitive task in your business, there’s probably a smarter way. Whether it’s sending pay stubs, onboarding new clients, or collecting form data, automation tools like Google Apps Script can save time and sanity.

Got something in mind you want to streamline? Let’s talk! I love helping people build systems that work without the headache.