Hello, I’m Curtis Deprey, an Account Executive specializing in Employee Benefits at Midwest Select Insurance Group (MSIG). I’m based in Eau Claire, Wisconsin, but my role often takes me on the road. Some weeks, I travel every day, while others I’m only out one or two days, depending on the needs of my current and prospective clients. What I enjoy most about my career is connecting with people, especially business owners, and providing them with solutions that make a meaningful impact in their organizations.
Learning by Doing: My Journey into the World of Insurance
I entered the insurance industry in 2017 with no prior experience, and that first year was a transformative learning period. I immersed myself in understanding the products we offered, shadowed experienced agents during client meetings, and observed a variety of sales techniques across different business settings. I was fortunate to be surrounded by an outstanding team of MSIG colleagues who were not only knowledgeable but also generous with their time and support, always eager to mentor and help others succeed.
One of the most formative experiences early on was writing individual health plans. This hands-on work taught me how to effectively read and interpret a Summary of Benefits and Coverage (SBC), a core skill I continue to rely on today. Mastering sales is a long journey, yet the process is filled with valuable insights and, at times, a great deal of fun.
Support That Fuels Success: Why MSIG Is the Ideal Starting Point
Starting an insurance career can feel overwhelming, particularly when faced with the uncertainty of commission-based compensation. However, one of the biggest advantages of joining MSIG is the unparalleled support system they have in place. With a well-structured onboarding process and hands-on mentorship, MSIG empowers new agents to begin earning income quickly and confidently.
The agency has successfully trained dozens of agents who continue to thrive in the industry today. For individuals without prior experience in insurance, like I once was, MSIG provides the ideal foundation to build a lasting career in insurance. With the right tools, guidance, and support, achieving success here isn’t just possible, it’s highly attainable.
The Rhythm of Sales: Learning, Adapting, and Growing at MSIG
After years of refining my skills, educating, and working closely with clients, I’ve come to truly value the variety that each day brings. Some days are spent in the field, enrolling new employees at client locations; others are dedicated to office-based responsibilities like responding to emails, making follow-up calls, or prospecting for new clients. On any given day, I may handle anywhere from 20 to 100 emails and make 10 to 50 calls. While not every day is exciting, most are incredibly rewarding.
Personally, I find in-person prospecting days to be some of the most fulfilling. Yes, walking into a new business cold can feel daunting at first, but with the support and solutions MSIG provides, each visit becomes an opportunity to make a real difference in an employer’s life. Sales is a continuous journey of growth, and everyone learns differently. I thrive through hands-on experience, but others may find reading or listening more effective. The key is to understand how you learn best and stay open to evolving and improving every day.
More Than a Team: The Family Culture at MSIG
As many would agree, the people you work with play a significant role in your life, and at MSIG, we truly feel like family. From the newest agent to the most seasoned professional, everyone is treated with respect, supported in their growth, and given the time and resources needed to succeed.
We work hard, but we also make time to celebrate, connect, and enjoy life as a team. MSIG actively promotes a healthy work-life balance — one that supports our commitments both inside and outside the office. Many of us are deeply engaged in our communities. I’ve had the privilege of serving as PTA President at one of my children’s schools, coaching their sports teams, and attending their important events, a balance I deeply value and appreciate.
About the Author
Curtis Deprey is an Employee Benefits Account Executive at Midwest Select Insurance Group. He is dedicated to helping small to large businesses implement high-quality, cost-effective benefit solutions tailored to attract and retain top talent while aligning with company budgets. Curtis partners closely with employers to design plans that deliver real value to both companies and their employees.
A proud Eau Claire native, Curtis graduated from Memorial High School, where he was a varsity hockey player and a member of the 2008 Wisconsin State Championship team. Since joining MSIG in 2017, he has built a strong reputation for providing hands-on support, clear and responsive communication, and creative, client-focused solutions that drive long-term success.
Beyond his professional work, Curtis is deeply committed to serving his community. He spent seven years as President of the Board of Directors for the Epilepsy Foundation of Wisconsin and also served on the foundation’s national board. In recognition of his contributions, he was honored with the organization’s prestigious Legacy Award in 2023. Curtis currently serves as PTA President at a school within the Eau Claire Area School District and remains actively involved in coaching youth hockey.
