Meet the Leadership Team

Jeremy Cardenas is the Principal and Founder of Midwest Insurance Group, a successful and growing agency based in Delafield, Wisconsin. Since founding the agency in 2000, Jeremy has led with vision and dedication, building the business from the ground up as a first-generation agency owner. He chose the name Midwest Insurance Group to reflect his commitment to serving clients across the entire Midwest region.

As a hands-on leader, Jeremy is actively involved in every facet of the agency—from strategic acquisitions to mentoring team members and sharing his deep expertise in insurance products, services, and coverage solutions.

Jeremy earned his degree in Economics with a minor in Insurance from the University of Wisconsin–La Crosse, where he also distinguished himself as an NCAA All-American wrestler. In addition, he proudly served six years in the Army National Guard, bringing discipline and leadership to both his military and professional endeavors.

Outside of the office, Jeremy is passionate about spending time with his family, staying engaged in the local community, and traveling. A dedicated fitness enthusiast, he prioritizes an active lifestyle. He is also a supporter of Wisconsin’s sports teams.

Steve Pape has been with Midwest Insurance Group since 2002, serving as Vice President of Business Development. With over two decades of industry experience, Steve leads the agency’s commercial insurance marketing and placement strategy, overseeing a skilled team of marketing specialists. He plays a critical role in maintaining strong relationships with insurance carrier underwriters and personnel, ensuring the firm delivers well-placed, competitive solutions to clients.

Known for his hands-on leadership style, Steve is also involved in mentoring and training new commercial producers—helping them develop a solid understanding of products, coverages, and client-focused services. He thrives on problem-solving and brings together teams with diverse expertise to collaborate on customized risk management strategies for businesses of all sizes.

Steve values the camaraderie and collaborative culture at Midwest Insurance Group. He believes that bringing the right people together leads to smarter, more innovative outcomes for clients.

When he's not at the office, Steve enjoys spending time with his family, tackling home projects, cheering on the Milwaukee Bucks and Green Bay Packers, or exploring the outdoors while camping with his wife, Beth, and their son, Monty.

Crystal Benson is the Director of Operations and Managing Partner at Midwest Insurance Group, where she leads the agency’s day-to-day operations with a strategic focus on efficiency, growth, and team success. She oversees key departments including commercial and personal lines, employee benefits, accounting, and human resources.

Crystal is passionate about employee development and places a strong emphasis on retention by fostering professional satisfaction and a supportive work culture. Her leadership style prioritizes clear communication, collaboration, and continuous improvement.

She is responsible for driving acquisition strategy, streamlining internal processes, managing financial and administrative functions, and fostering a high-performing team culture. Crystal holds several professional designations—AIC (Associate in Claims), CPIA (Certified Professional Insurance Agent), and CIC (Certified Insurance Counselor)—demonstrating her commitment to professional excellence.

Beyond the office, Crystal is dedicated to family, fitness, and community—often on the sidelines at her kids’ games, enjoying time outdoors, or participating in local events.

Matt Wallace brings 27 years of insurance industry experience to his role as Sales Director and Managing Partner at Midwest Insurance Group. With deep expertise in mid-market commercial insurance, Matt has built a distinguished career helping businesses across the region protect their assets and manage risk.

As a seasoned sales leader, Matt has spent the past five years leading Midwest’s strategic initiatives and business development efforts. He is energized by the challenge of developing successful sales professionals and takes pride in the team’s results. Over the past 5 years Midwest has doubled in size and is well positioned for future growth.

In addition to his management roles, Matt still works directly with his clients and strives to grow his personal book. Throughout his career, Matt has developed a reputation for building lasting client relationships by providing excellent service, communication, and embracing the evolving insurance landscape with a unique focus on data analytics.

Outside of work, Matt enjoys spending time with family, coaching youth sports, and getting outdoors as much as possible.

Coming Soon!