Small Business Health Insurance | MN Benefit Packages Small Businesses

Providing Employee
Benefit Packages
for Small Businesses

Benefit Solutions That People Understand


The Cleveland Company has been an industry leader in employee benefits consulting in the Twin Cities for over 25 years. We value long term relationships with our clients and are well-respected by our insurance carriers. Every day we come to work with one goal in mind:
To help people.


The Cleveland Company works closely with client companies to help employees make smarter benefit choices while navigating the current financial trend that increasingly exposes employees to new, difficult and expensive choices.


Our distinct specialty is creating success stories in this challenging, complex world of employee benefits. We serve real people with real problems by working closely with employers who care about their employees.

Chief Financial Officer / Benilde-St. Margaret's School

Natalie Ramier

We have been very happy with The Cleveland Company.  They have helped us navigate the constantly changing world of health insurance and other employee benefits.  I feel like we have been able to provide our employees with a high level of benefits while managing costs both for the employee and the organization.  Thanks for all you do!

Dan Delmore

One of the greatest challenges facing small business owners is the daunting task of staying ahead of all the regulatory changes and mandatory disclosures.  My company health insurance puzzle was solved the day I began to work with Michelle Maher and The Cleveland Company.  Michelle’s knowledge of the industry and the myriad of regulatory government changes has enabled me to provide coverage for my employees in an affordable manner.  She also has the skills necessary to present to my staff how the program will affect their personal health care situation.

Client Snapshot

Cleveland Company helps clients by working with their employees to make decisions that will protect their assets, grow their wealth and preserve it from risk. Our number one priority is to help your employees understand their financial risks through education.

  • Between 2 – 200 employees
  • Want to attract and retain high value employees
  • Confused about benefits options and want an expert opinion
  • Needing help with compliance and ERISA
  • Wondering what the heck a 1095 C form is
  • Seeking assistance figuring out what is the best benefit admin system
  • Concerned over payroll integration
  • Wanting help meeting other professional business service providers, such as: banks, financial institutions, private equity funding, building leasing, temporary staffing, and marketing
  • Searching for knowledge and information about benefits

If this is you or your company, then the Cleveland Company is for you!

The Cleveland Company began as an employee benefits consulting firm that helps employers create a caring culture. We are seasoned professionals who understand that employers are faced with the biggest challenge in years: how to continue to offer a quality employee benefits program, yet help employees navigate their additional financial responsibilities.

SPHR, Human Resources Director / ImageSensing Systems

Becky Degendorfer

The Cleveland Company has been a trusted partner of ImageSensing Systems (ISS) for over a decade.  They have aided our organization in remaining competitively aligned by offering our employee’s top tier, affordable healthcare and benefits.  At the same time The Cleveland Company helped ISS manage the financial impact of a dynamic, often difficult to understand, healthcare environment.  Additionally, their customer service has been outstanding.  The knowledgeable team at The Cleveland is always ready to roll up their sleeves to help us meet the needs of ISS employees.

Training Manager / Lifecore Biomedical

Leah Bredehorst

Our organization has worked with The Cleveland Company for 25 years.  Throughout that entire time, they have been an invaluable business partner.  They have kept our organization aware of regulatory, legal and business practice changes in the industry and provided appropriate resources and solutions.  The staff at The Cleveland Company has always responded to our needs and requests in a very timely manner.  They truly put their customers first.    They are not only our broker, but our advocate.


As a Trusted Advisor to your business, The Cleveland Company conducts in-depth discovery regarding client’s business mission, goals, plus vision for their benefit plan. They collaboratively work with clients to jointly create innovative, synergistic programs that are specifically designed meet company needs.
An ongoing commitment to the client providing on-going resources, for related service providers, sets the Cleveland Company apart.


The cornerstone of our business is working diligently to create a culture of care by providing education, direction and support to enhance the financial security of clients and their employees. It means that your benefit plans reflect that you care, then your employees will feel good about working for your company and that your company culture is a Culture of Care.

Trusted Advisor Network

We have a comprehensive network of other services that business owners need, so you don’t have to know everyone. Just give us a call and ask. We only refer you to people that we have known a long time and trust.

  • Employment Law professionals
  • Executive Benefits
  • Executive Coaching
  • Compensation Planning
  • Employment – both temporary and perm placement
  • Building Leasing
  • Financial services: bank, credit Unions, accountants, short term cash flow
  • Equipment leasing

Call Us For Referrals

Director of Human Resources / QTS

Nicole Dodge

The Cleveland Company has been a respected and dependable partner to us for over 8 years.   In working with John and his team we find them to be extremely reliable, responsive, and resourceful.  They are proactive in staying ahead of industry trends to provide services and solutions to meet the changing landscape.  In addition to a welcoming and friendly staff, one of the things we also value is that information is presented in a manner that can be understood and appreciated by all audiences.

Are You Looking For Individual Health Insurance Options?

Find the best health plans for you and your family with our no obligation health insurance marketplace.

Awards & Licensure

“Our commitment at the Cleveland Companies is to educate you, help you make the best decision for your business while holding ourselves to the highest ethical standards.”-John Cleveland

The Cleveland Company is active in The Twin West Chamber of Commerce and the Minnesota Chamber of Commerce.
Mr. Cleveland earned a Charted Life Underwriter (CLU), the premier credential in the insurance profession, representing eight or more comprehensive college-level courses covering all aspects of insurance planning, estate and retirement issues, taxation, business insurance, and risk management. In order to maintain his licensure Mr. Cleveland must also complete a minimum of 30 hours of continuing education every two years, adhere to strict ethical standards, and meet extensive experience requirements, thus ensuring the knowledge you’re counting on is both comprehensive and current.
Ms. Maher, holds a Fellow, Life Management Institute designation. The Fellow, Life Management Institute (FLMI) program is a 10-course professional development program that provides an industry-specific business education in the context of the insurance and financial services industry. The FLMI teaches advanced insurance and financial concepts to build a deeper understanding of the insurance business. Established in 1932, the FLMI program is the world’s largest university-level education program in insurance and financial services.
The entire team at Cleveland Company is licensed by the state of Minnesota with Health, Life and Accident Insurance credentials. That way you know you are speaking with an insurance professional who understands you and your business needs, as well as the regulatory and compliance issues.

Three Years in a Row

Five Star Professional conducts research to help consumers with the important decision of selecting a service professional. The Five Star award is presented to wealth managers, real estate agents, mortgage professionals, insurance professionals and dentists in more than 45 markets in the U.S. and Canada. The Five Star award recognizes service professionals who provide quality services to their clients.
The Cleveland Company is a proud recipient of The Five Star Award in 2010, 2011, 2012 – every year Five Star Professional presented the award in the Twin Cities.

Contact Us Today

The Cleveland Company is ready to help you understand and solve any and all of your benefits problems.

UBA is the nation’s leading organization of independent benefit advisors who are bound by a code of conduct to actively cultivate, validate and share wisdom with busy benefit decision makers nationwide who want peace of mind through trust in knowing they are making informed choices in a complex marketplace.
UBA believes in service and genuine sharing through mutual trust. Their culture, as is Cleveland Company’s, is one of honesty, transparency, and making others better. It is defined by the values of integrity, collaboration, care for others, innovation, and operational excellence.
Our association with UBA allows you, as a valued client of Cleveland Company, to harness the collaborative power of thousands of benefits experts and build a benefits package that meets your individual needs.

InsureEasy is an insurance marketplace with real people helping you find and understand the best health plan at the lowest possible cost.
At the website, you can answer a few easy questions to determine the best plan for you. You can also receive complementary assistance from licensed professionals, or shop on your own for Major Medical, Short term medical, Accident and Illness, Dental, Vision, and travel Medical insurance. On the page, you’ll also find helpful information including tax credit calculators, a glossary of helpful insurance terms, and FAQ sheets loaded with information. The best thing about InsureEasy is when you call, you’ll speak with a live person who has been trained and licensed in individual healthcare plans.
Plus !Se Hablos Español! Yes, we have an insurance licensed native Spanish speaker on our team.

Additional Partners