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About Us


Planning Futures

We have years of experience helping our employees meet their financial goals. Ask us about:

  • Financial growth
  • Flexible Schedule
  • Career development
  • National growth opportunities
  • Leadership Academy
  • Six-figure income
  • Investments
  • Retirement planning
  • Continued education 3x annually
  • Travel (Cabo, Las Vegas, Seattle) etc.

 We believe in the people who believe in us.  That's why all of our employees receive continued and ongoing training, clear set career tracks, nationwide support as well as one-on one mentor-ship. Setting our employees up for success helps them, help you. 


Giving Back

To the Stenglein Agencies, it is about more than just insurance. Giving back to communities is a central part of our philosophy, and we want to offer an exciting career to those who share our vision for helping others. 


Committed to Service

We believe in the Platinum Rule: Do more for others than you would have done for your self.  Serving our customers is our number one priority.  We are here for the working class.

Top Employer



Patrick Stenglein

Partner and Vice President of Sales

Wisconsin | Minnesota | Nevada | Utah| California| Iowa| Washington | Idaho

Patrick started his career in 2003 and has expanded the business across the nation.  As a recent graduate, with little experience, Patrick knew he had a passion for working with people.  His father, at a young age, instilled the value of seizing an opportunity when it presents itself. Patrick's opportunity came in 2003 when Patrick was recruited into the business by his older brother Ryan.  Growing quickly in Minnesota, Patrick was rapidly promoted into management, and was offered the opportunity to run Iowa.  Knowing this was an incredible opportunity, Patrick left his Minneapolis roots.  And so began Patrick's journey.  Over the last 15 years, Patrick has developed leadership throughout Minnesota, Iowa, Washington, California, Nevada, Utah and Wisconsin.   To date, Patrick has developed multiple top leaders in the company including, Partner Nick Lorence, Leader of the Year and number one Regional General Agent Mark Nielson and Top Regional Director Patrick Rieger.  Knowing that investing in the team, that invests in our customers was key, Patrick found success.  He has been Leader of the Year as well as Vice President of Sales, and has now taken a Partner opportunity.  Recently, Patrick has focused his efforts on developing the state of Wisconsin and enjoys spending time with his two dogs, and his family

Regional Leadership

Drew Severson
Regional Manager
Milwaukee | Las Vegas | Minneapolis

Andrew Severson

Regional Director

Milwaukee | Las Vegas | Minneapolis

A Minneapolis native, and favorite local bartender, Drew had made his way in the hospitality industry for over 8 years.  Once he realized that he needed a long term career to invest himself in, Drew took his people skills and work ethic and applied them to the storm damage industry. Unfortunately that was too seasonal and did not provide the stability Drew was seeking. He started with the Stenglein Agency over 4 years ago and is currently a top performer who has developed top offices across the country.  Drew loves a good happy hour, spending time with his son Aiden and traveling to company conferences in Puerto Rico, Cabo and Las Vegas. 


Cody Allen

Managing General Agent

Milwaukee | Wisconsin

A 2009 Graduate from Beloit College, Cody majored in Communications and Business Management. Campus involvement included earning Captain of his football team, as well as being Vice  President of Sigma Chi fraternity his senior year. Cody enjoys spending his days with his wonderful wife Chanda, as well as his pitfall terrier, formally known as Prince. They enjoy music festivals, trying new recipes and of course delving into new series and shows.  Cody wanted to use his leadership skills in a professional atmosphere, and take his career to the next level.  He is currently being mentored by Patrick Stenglein and Andrew Severson.  Cody has quickly taken leadership in guiding others in the office with their education and training o


Jon Willman

Managing General Agent

Born and raised in Appleton, Wisconsin, Jon recently moved to Milwaukee for the job. He graduated from St. Norbert College in 2016 with a  Bachelors degree in Communications. Jon made the transition to the financial industry after not finding the income and true growth opportunity after years in car sales.  When he isn't working he is spending time with his wife Morgan and exploring the Milwaukee area. He also enjoys watching his favorite teams like the Packers, Bucks, and Brewers. Jon is excited to part of the team and to protect families in the community. 



Alyssa Harmsen

Office Manager

Alyssa Harmsen was born and raised in Waupun, Wisconsin. She grew up being very involved in various activities, sports, clubs, and volunteer organizations, however, her favorite was gymnastics. Alyssa graduated from UW-Whitewater in December of 2017. She currently lives in Oconomowoc, Wisconsin with her fiancé, Jordan. When she isn't working, she spends her free time with Jordan, visiting family, catching up on TV shows, or hanging out with her friends having margaritas.

Alyssa is excited to be a part of the team and helping to make a difference in the community through her work.


Open Positions

Entry Level Management | M-I-T

Top Work Places for Training & Growth Opportunities

Forbes Happiest Places to Work | Seattle Top 100

Our international company has been steadily growing for over 20 years. With a huge push in company culture towards training, our youthful energetic team enjoys professional development through: one on one mentor-ship, classroom style learning and will fly to leadership and development conferences across the nation three times annually.These are state of the art conferences with training from top performers across the US and Canada.

This selective position will focus on quickly advancing into Territory Management. We focus on charisma, drive, professionalism and goal orientation and will be looking for this in our ideal candidate, as well as a natural ability to gravitate towards leadership.

The Manager in Training will be working with their clients over the phone and face to face, in a dynamic team oriented environment. This position is geared toward growth, financially and professionally. Our team members will go through training to take on leadership after 3-5 months, to become a Supervising Associate responsible for a team of newer associates in office.

We are looking to interview this coming week, to prepare leaders for the next schooling in February in Cabo San Lucas.


Grand Opening

Ribbon cutting ceremony 2018.  Our entire team was featured in publications across Milwaukee!  

Contact Us

Schedule an Interview or Request a Visit from an Agent

Stenglein Agencies

125 North Executive Drive, Ste. 310 Brookfield, Wisconsin 53005, United States

507 459 5807 opportunities@stengleinmidwest.com


Monday - Friday: 10am - 5pm

Saturday: By appointment

Sunday: Closed