Three Generations Strong

Sam and John Cleveland, father and son, formed the Cleveland Company in 1988. Bringing their practices together fostered an important purpose:

Guide companies toward benefit programs that attract and retain the best talent by providing the greatest possible financial security to employees and their families.

The apple doesn’t fall far from the tree, nor does the fruit it bears. Along with the next generation, we continue to make this mission a reality today through intentional plan design and effective, understandable financial education. Our firm continues to grow, in size, scope of service, and generationally making us well poised to be one of the premier private, family-owned benefit firms in Minnesota.

Meet Our Team

John Cleveland, CLU

Employee Benefits Consultant

Michelle Maher, FLMI

Employee Benefits Consultant

Amy Berge

Account Manager

David Budin


Tony Cleveland

Employee Benefits Consultant

Pam Kratky

Assistant Account Manager / Individual Plan Sales

Kathy Maher

Assistant Account Manager

Karwyn Meyer

Senior Account Manger

Herbert Roldan

Account Manager

Jen Samson

Account Manager

Pete Samson

Employee Benefits Consultant

Ryan Soule

Employee Benefits Consultant

Nancy Stone

Senior Account Manager

Janet Walker

Individual Plan Sales