Hi, I’m Brendan Dooley, Vice President of Commercial Insurance at Midwest Select Insurance Group (MSIG). I’m based in Eau Claire, Wisconsin, but most days, you’ll find me on the road meeting clients, coaching other agents, or winning the next great account. Today, I want to give you an honest look into what a day in this career is like, the pace, the people, the challenges, and why I wouldn’t trade it for anything.
Getting Started in Insurance: From Intern to Agent
I got my start in 2018 as a marketing intern at MSIG, just after graduating from Memorial High School in Eau Claire. Over the next few summers, I’d return from college at UW-Madison to work at MSIG, setting appointments, assisting with quotes, creating brochures and proposals, and, most valuably, shadowing experienced agents as they met with business owners. That hands-on experience showed me how insurance isn’t just about paperwork, it’s about forming relationships and solving real problems.
What a Typical Day Looks Like: No Two Days Are the Same
Now, several years later, my daily routine looks nothing like it did when I first started. After hitting the requirements of our partnership program, I became a partner and now lead our commercial insurance team, which has made the journey both rewarding and, of course, fun. Some days, I’m on the road meeting with business owners across the Midwest, who run everything from large manufacturing operations and construction companies to small nonprofits. Other days, I’m training new agents, helping them close their first deals, or showing them how to break down policy coverages.
I wear a lot of hats: interviewing new agents who have applied to our agency, designing our marketing strategies, meeting with underwriters and carrier reps, attending networking events, pursuing new accounts, and most importantly, making time for current clients. Visiting our clients face-to-face is one of MSIG’s core service principles.
Building Relationships, On the Road and In the Office:
I have developed strong relationships with my current client base by demonstrating experience and responsive service, and due to this, I receive a lot of referrals (I even receive them from other insurance agencies when they can’t place a risk). Last week alone, I obtained four commercial leads, which kept me very busy. However, I always try to make time to visit at least one existing client whenever I’m on the road. Whether it’s reviewing their renewal, helping with a claim, adding new coverage, or just catching up, those visits are key.
While driving, I’m almost always on the phone—answering agent questions, talking to underwriters, checking in with my marketing team, or chatting with clients. When I’m in the office, you’ll find me reviewing quotes, collaborating with other agents, conducting interviews, and ensuring operations are running smoothly with our service team.
Why MSIG’s Model Works: Built-In Team Support
At MSIG, we don’t throw agents to the wolves. Every new agent starts with a mentor. You’ll always have someone to learn from, ask questions to, and someday, hopefully, become a mentor yourself.
Even now, I always try to travel with another agent. It allows us to bounce ideas off one another, split tasks, and, honestly, makes the work more enjoyable. Teamwork is built into our culture, and we believe it’s essential for success.
Dual-Agent Books for Seamless Service
We promote agents pairing their books of business together, so if someone’s out on vacation, the other can step in without missing a beat. It also gives you the chance to collaborate and play to each other’s strengths.
Our “Work Hard, Have Fun” Mentality
We hustle — but we make time for fun too. Just ask Shannon Anderegg, who brought me and one of our clients skydiving last fall! Or Jason Phillips, whom I might sneak off with to fish a trout stream or chase some birds after a long day of meetings.
Why I Love What I Do: The Challenge
If there’s one thing that keeps me hooked on this career, it’s the constant challenge. I love chasing new business. Even after landing a large account, I’m already thinking about the next one. That hunger is what makes a great agent.
It’s not easy. We use dozens of carriers, and each one is different. That means we’re constantly learning, refining, and paying close attention to details. But that’s how we win accounts and provide real value to our clients. We don’t just sell policies; we learn about our clients’ businesses and begin to understand them as well as they do sometimes.
Creating Long-Term Relationships
There’s nothing better than seeing a client year after year and being their go-to resource. When respected business owners trust you with their most important assets, it’s incredibly rewarding.
It takes time, consistency, and great service, but once you earn that trust, there’s no better feeling in this industry.
Could This Be Your Career Too?
I’ve worked with businesses of all shapes and sizes — from solo operators to 50+ employee shops — in industries like trucking, plumbing, landscaping, roofing, daycares, and even propane haulers. What ties them all together is the need for strong coverage and a team that’s always in their corner.
If you’re someone who thrives on variety, enjoys working collaboratively, and wants to build something meaningful with the potential to become a partner, then a career in insurance at MSIG might be the perfect fit.
Learn more about careers at MSIG here.
About the Author
Brendan Dooley is the Vice President of Commercial Insurance at Midwest Select Insurance Group, specializing in helping business owners across Wisconsin and throughout the rest of the country get high-quality coverage with a team they know and trust.
Born and raised in Eau Claire, Brendan started his insurance career at MSIG in 2018 after graduating from Memorial High School. He earned his insurance license soon after while attending the University of Wisconsin School of Business, which he graduated from in 2021 with a degree in Marketing. He lives in Eau Claire, WI, and when he’s not meeting with business owners or mentoring new agents, you’ll find him fishing the Chippewa River or trout streams around the Valley.
