Leading from the Ground Up: Courtney Boles on Captive Insurance, Career Growth, and Getting Involved

We recently caught up with Courtney Boles, director of operations at Management Services International (MSI), about her career path in the insurance industry and the operational realities of running a captive insurance company. In this Q&A, she reflects on what it takes to build credibility, involve the right stakeholders, and approach a captive as a strategic business tool—not just an expense.

Photo of Courtney Boles provided courtesy of MSI

You've had an impressive rise in the insurance world. How did you work your way up from administrative assistant to senior leadership?

I started in the industry as an assistant at an independent regional insurance brokerage. Over the 5 years I was there, I earned my insurance license and Microsoft and Certified Risk Manager certifications, and I moved into a role directly supporting the president and sales team. I realized pretty quickly that the closer you are to the top, the more you get to see. You learn by doing. Revenue equals freedom. And when you can show how your work generates profit, people pay attention. I also came to understand that executives aren't mystical creatures with some kind of secret talent—they're just people. And with the right knowledge, I could do what they did.

I stepped away from insurance for about 5 years, but when the economy shifted, I found myself taking another administrative role in the industry. This time, though, I was upfront from day one: I wasn't looking to be an executive assistant for long. I wanted a real seat at the table.

It was a small company with plenty of business and not enough staff. I was supposed to focus on sales support, but I quickly found myself reviewing policies, managing captive formations and regulatory tasks, training on CRM workflows, monitoring the pool, writing operations manuals, authoring articles, and navigating a buyout—basically doing whatever needed to get done that no one else had time for.

I also started taking things off my bosses' plates and handling them myself—sometimes asking forgiveness rather than permission. I built relationships across the organization and advocated for my own advancement. It started gradually: first managing a temp, then an admin, and eventually a full team of analysts and admins. Honestly, it took longer than it should have. I was often doing the job before I had the title or the pay. That experience made me a big believer in promoting administrative professionals who want to move up. More often than not, they rise to the challenge when given the chance.

To this day, I approach every role with an "I may not know, but I'll figure it out" mindset. That's what led me to my current position as director of operations at MSI. Understanding the business from the ground up—and how people think at every level—is a huge advantage. It helps me lead teams more effectively and, hopefully, inspires others along the way.

What's the smartest way to bring all the key players into the captive formation process?

Get them involved early. Help them understand the purpose of the captive and get their buy-in. Let them collaborate on setting the captive's goals—and, if possible, give them a stake in its success.

From an operational standpoint, what needs to be in place to successfully set up and run a captive insurance company?

A business should consider how its current risk management strategies, risk tolerances, and cash flows will be incorporated into the captive. It's also important to identify who needs to be involved—externally, which might include insurance brokers, financial institutions, and investment managers, while internally, it could involve key members of the finance or risk teams. They should be able to define what success looks like for the captive and have a plan in place if it isn't measuring up.

What education is essential for businesses setting up a captive insurance company, and how can they make sure everyone is aligned?

Captive 101 is the initial education—what risks can be covered and how, the different captive structures, and available domiciles. It's typically attended by the owners of the business that will be insured.

Then there's the feasibility study. That's a specific analysis of the risks that can and will be insured, and it may include different deductible options or levels of insurance. Ideally, it's shared with the business owners, the insurance broker, and the organization's risk management team.

Captive 201 comes once the captive is established. It's about setting expectations—things like annual reporting requirements, key meetings, the importance of getting regulatory approval before making changes, and the need to revisit coverage as the business changes. The goal is to make sure the captive is doing what it was set up to do. That session should include the business owners and their financial and risk teams.

And finally, there's the claims conversation. That's when the captive manager walks through the policies with the business owners, brokers, department heads, and anyone else involved—explaining what's covered, what could count as a claim, and how to report it. This is especially important when the captive is covering things that used to just be business expenses or wrap around commercial insurance.

What's the biggest operational challenge companies face once their captive insurance company is up and running?

The big challenge is shifting your mindset—starting to think about insurance as a tool and a business you own, not just another expense. In the commercial market, you're usually trying to present everything in the best possible light to get the lowest rate. But with a captive, it's yours. You don't need to polish things up. Be honest about what could happen or what you've seen others in your industry struggle with. That's how your captive can start building real solutions for those risks.

It's the same with claims. Report anything that might be one—even if it's uncertain—because there might be coverage. And even if there isn't, it could help you identify new risks your captive should consider covering in the future. Dream big. If your captive can't insure it now, maybe it can later.

And for business owners who are used to moving fast, just remember: A captive is a regulated entity. You'll need to run changes past your captive manager and get approval from insurance regulators first. They're usually pretty reasonable, but their job is to protect the insureds and make sure the captive stays compliant and financially sound.

What kinds of opportunities should captive owners and managers be exploring more actively?

Customization is a big one. I like to compare traditional insurance to the six o'clock news we all used to watch—you had to tune in at their time and listen to the stories they chose to tell. Now, we scroll through our phones when we have a minute and see the stories that actually interest us.

Captives work the same way. You get to focus on the risks that matter most to your business and build policies and processes around those. You can manage them in a way—and on a timeline—that fits your needs. Captives also give you the opportunity to insure emerging risks that the traditional market may not have the capacity for yet. It's kind of like seeing breaking news on X before the big networks even catch up.

There's also the cost savings. A captive can strengthen your negotiating position when buying commercial insurance, letting you take on higher deductibles or more of the risk. And if it's properly underwritten—and with a little luck—it can even turn a profit, just like a commercial insurer.

And then there's control. Business owners like control. With a captive, you're in charge of how you manage your risks. You can decide whether to settle, mitigate, or litigate—rather than having to follow what the insurance company says. You set the exposure levels you're comfortable with, use reinsurance to cover the rest, and design deductibles and reporting structures that make claims handling more efficient.

Finally, how do you think the way businesses operate their captives will evolve in the coming years?

Underwriting, claims, and financial reporting will keep evolving as artificial intelligence makes it easier to process large amounts of data. I think we'll also see more parametric underwriting for the same reason—technology is making it more accessible and scalable.

I also believe captives will become even more collaborative. Insurance brokers are starting to see captives as partners rather than threats, which is a big shift. And more organizations are recognizing the value of involving their entire leadership team—and in some cases, all employees—in understanding how risks are managed. When people across the organization understand how a captive works and how it fits into the broader risk strategy, they can contribute ideas. Internal teams often know better than anyone where the real threats and opportunities are, and that input helps make the captive more effective and aligned with the business.