Employee Spotlight Mike Shepherd

Tell us about your professional background before Steele. What kind of career did you lead?

For about 10 years, in Seattle, I worked in employee benefits on the broker/consultant side of the industry. I was also an international and professional rugby player for 15 years.

When and how did you get involved with Steele Benefits? I started with Steele in April 2023. I knew the Steele family, having grown up in Brownsburg. I was in the same grade as Brett, and we were buddies over the years. In fact, Mike Steele was my basketball coach in 4th grade. When I knew that I was moving back to Indy from Seattle, I made sure to engage with the Steele team for introductory conversations. That led to an opportunity for my current role, soon after we moved back home to Indy.

How would you describe your role in one sentence? My job is to grow our reach and positive influence with employers, their people, consultants, and industry partners.

What does a typical workday for you look like? What is a typical day? Most days include consultation and strategy with prospective, new, or existing customers, along with broker channel partners and carriers in the industry. I also explore the region for new connections and events to help promote Steele’s good works and to empower employers with our solutions. Market research and analysis are always a to-do, along with orchestrating professional development and innovations for the team and me.

Do you have a favorite Steele memory? My first User Meeting was a revelation of how impactful the event and Steele are to our customers. It was great to engage with everyone in person and to hear countless stories of our team members going above and beyond.

Anything else you might wish to mention? Steele is such a balanced workplace. We’re all challenged to stay curious and to grow, to work hard serve our customers well, and to help our teammates the best we can. With that, we are sure to have a ton of fun. Steele is very dynamic and nimble, which sets us apart. The team-centric work culture has been very valuable to me.

Outside of work, what kind of hobbies do you have? I enjoy the outdoors with my family. I play golf, fish, travel, cook, and enjoy watching sports & movies.

What’s an interesting fact not many people know about you? My wife and I met in show choir & madrigals, back in high school.

If you wrote a book about your career so far, what would you title it? Why? Benefits and Bruises: The Life of an Insurance/Rugby Professional.

If you had a warning label, what would yours say? Warning: Will break out into song. I have a tough habit of associating daily words or phrases with song lyrics. From there, that song is stuck in my head until it happens again.

What celebrity would you like to meet at Starbucks for a cup of coffee? Mark Cuban. He and I are both IU Rugby Alumni, and I owe him a coffee but specifically, a beer. Beyond that, his professional and entrepreneurial successes are interesting to me. I’d like to bend his ear on his recent impacts on healthcare, too.

What’s the most daring thing you’ve ever done? I took a big leap with my rugby pathway, many years ago. I decided to pursue rugby to the highest levels that I could, instead of other opportunities. It is more so “daring” in the States than in other parts of the world, but I would not change my decision if I had the chance. My family was wildly supportive of me and was a big part of my journey, stateside and around the world.

If you had a time machine, would you travel to the future or back to the past? I would go back to when my kids were newborns and revisit that special time. As everyone warned me, it goes by so quickly and I would go back to soak it all in and experience that special time as a young family.

If you could have a superpower, what would it be? Supersonic speed because I’ve never been “the fast guy” on any sports team that I have been on.

Are you related or distantly related to anyone famous? I have a very distant relative, through my in-laws, named Mark Summers. You may remember the many times he was ‘slimed’ in the 90s.

What’s the very first job you had (that’s not on your resume) and what did you learn from the experience? I worked in landscaping for family and friends for several of my younger years. I learned the value of hard work and finishing the job that you start.

What would you sing at Karaoke night? My go-to is “This Is How We Do It” by Montell Jordan.

Where and what is your dream vacation? A round-the-world tour of exciting and historic regions, landscapes, concerts, rugby games, interesting foods, and Disney Parks.

If you could jump into a pool of anything, what would it be full of? Ice Cream

Who is your most embarrassing celebrity crush? Back in the day, I had a big crush on Ashley Simpson for a short while. Her reality TV show and a couple of hit songs had me swooning.

What’s the silliest way you’ve ever gotten an injury? I managed to hurt my elbow during a kickball fundraising game. Yes, it’s possible.