Chris McIlroy never expected insurance to become his second career.
For 16 years, he worked as an engineer in the oil industry, a career that took him from California and Colorado to Houston and even Saudi Arabia. Then the COVID-19 pandemic brought that chapter of his life to an unexpected close.
Back home, McIlroy began thinking about what he wanted to do next. He knew he wanted to build something of his own, but he also wanted his work to have a personal connection to the people around him.
Insurance turned out to offer both.
“It was an unexpected choice at the time, but looking back on it, I’m super happy,” he says.
McIlroy began by offering supplemental insurance products before expanding into medical coverage and eventually establishing McIlroy Insurance Group. Six years later, what started as an unexpected career change has become a business built around something McIlroy values deeply: relationships.
“We’re thankful for our partnerships with all of our clients and their employees,” he says. “We get to know them on a personal level, and we’re really trying to help them as much as possible.”
That philosophy shapes the way McIlroy approaches his work. Rather than simply handing an employer a list of plans, he takes the time to understand the company, its employees, and what they need from their benefits.
For McIlroy, those conversations can be surprisingly personal. He meets individually with employees to answer questions, explain coverage, compare deductibles, and determine whether a particular specialist participates in a plan. He also helps people navigate online tools and applications so they feel more comfortable using the benefits they have.
It’s the kind of hands-on approach that makes sense for someone who sees his work as an opportunity to help people prepare for circumstances they hope never happen.
McIlroy says short- and long-term disability insurance are among the benefits people often overlook, particularly younger employees who consider themselves healthy. But an unexpected illness or accident can quickly exhaust paid time off and leave a household without its regular income.
“Short- and long-term disability is really insurance for your paycheck,” McIlroy says. “You don’t need it until you need it. But when you do, you really need it.”
That desire to help people extends to the business owners McIlroy works with, too. He understands that employers are balancing their own budgets while trying to provide meaningful benefits for their teams.
“We’re really trying to find the best package and the best value,” he explains. “It’s about building a broad but affordable benefits package so employers and employees feel like they’re getting a good bang for their buck.”
He has seen how those decisions can affect much more than a company’s bottom line. For example, a med spa competing with hospitals to recruit nurses and nurse practitioners may need to offer competitive benefits to attract experienced professionals.
“The difference between a job and a career is benefits,” McIlroy says.
McIlroy Insurance Group’s busiest season is during open enrollment, which runs from Oct. 1 through Jan. 1. For companies with benefits renewing at the beginning of the year, McIlroy recommends gathering rates in October, selecting plans in November, and beginning enrollment by early December.
The holidays can make that window feel even shorter.
“Between Thanksgiving and Christmas, you’ve got about three weeks to get a whole lot done,” he says.
But even during the busiest time of year, McIlroy’s focus remains on the relationships that led him to embrace an unexpected second career in the first place.
Six years after making the leap into insurance, he says he’s grateful for the people he has met along the way and the opportunity to make a difference in their lives—one conversation, one question, and one carefully considered benefit at a time.