What COVID Taught Me About Staffing an Insurance Agency
When I started The WIN Agency, I assumed growth meant hiring the way every agency around me hired: find a licensed CSR locally, pay what the market demands, hope they stick around, and start the search again in eighteen months when they leave.
Then 2020 happened. We couldn’t bring people into an office. I had a growing book and nobody to service it. So I did the thing I’d been avoiding: I hired remote.
The first VA
The first person I brought on had no insurance background. What she had was a willingness to follow a process exactly, and I had a folder full of processes. Within a few weeks she was handling new and renewal quotes for home and auto, mortgagee changes, COIs, and the email inbox.
The thing that surprised me wasn’t that it worked. It was that it worked better than the in-office version. Remote team members following a documented checklist made fewer mistakes than local hires who’d been “trained” by sitting next to someone for a week.
Building the training program
Once I saw it work, I went all in. I turned my SOP library into a real curriculum: how personal lines quoting works, how carriers differ, what a mortgagee clause is, how to handle a client who’s upset about a rate increase. Every module ended with a task the trainee had to do correctly before moving on.
That curriculum became Agency Aid in 2023. Today we train virtual insurance specialists before they ever touch a client’s agency, and many of the people we place already have two or more years of insurance experience when they start.
What it changes for the owner
The economics are obvious, but the bigger shift is in how the owner spends their day. When quoting and service are handled by a trained remote team running on checklists, the owner gets back the only thing that actually grows an agency: time to sell and build relationships.
That’s the whole thesis behind everything I do. You don’t scale by working more hours. You scale by documenting what you do, handing it to people who will do it consistently, and protecting your own time for the work only you can do.
If you’re considering it
- Start with the tasks you do most often, not the ones you hate most. Volume is where a VA pays for themselves first.
- Write the process before you hire. A VA without an SOP is just another person waiting for you to explain things.
- Measure output weekly. Quotes completed, service tickets closed, response times. Numbers keep everyone honest.
- Treat them like team members, because they are. The best VAs I’ve worked with stayed for years.
COVID forced the experiment. The results are why I never went back.
Tyler Woodall is the founder of ScaleOps and Agency Aid. Read his story or browse more articles.