Experienced Insurance Guidance

Get Personalized Support That Takes the Stress Out of Insurance

Your Trusted Insurance Professional

Jake Zimmermann is an independent, licensed insurance agent who specializes in the Health and Life Insurance market. His primary business has been the senior market in Medicare Supplement, Medicare Advantage Plans and Medicare RX plans. He sells Dental and Cancer insurance as well as whole and term Life insurance. He also sells short term health insurance to individuals ages 64 and under as well. Jake holds insurance licenses in Wisconsin and Tennessee.   Read More About Jake 

Jake

Shop & Enroll in Medicare Online

Compare plans, explore your options, and enroll—all in one place.

Personalized Insurance Plans for Every Need

We recognize that your needs and situation are unique. We spend the time to get to know you to make sure that you get coverage and support that fits your lifestyle. 

Medicare Advantage

Medicare Advantage plans are new health care options that are part of the Medicare program. Coverage may include Medicare Part D prescription drug coverage as well as hospital, doctor, skilled nursing, and other medical services.

Medicare Supplement

A Medicare Supplement (Medigap) insurance, sold by private companies, can help pay some of the health care costs that Original Medicare doesn't cover, like copayments, coinsurance, and deductibles.

Medicare Part D

Medicare Part D is the federal government's prescription drug program that covers both brand-name and generic prescription drugs at participating pharmacies in your area.

 

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Pam Robinson Thompson

Nov 08, 2025 at 4:46 pm UTC

Being newly retired and new to medicare we needed help deciding what healthcare to choose. I went to Jake's class on medicare at the Sun Prairie library and learned alot. We chose traditional medicare and needed a supplemental medigap policy. Jake helped us pick Physicians Mutual medigap along with riders for dental, vision and a plan D prescription plan. We have been very happy with the choices and his help. Anytime I have a question I can email Jake for help. We highly recommend Jake to help with your insurance choices.

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John Duggleby

Nov 06, 2025 at 7:37 pm UTC

Jake is truly independent, and works hard to get my wife and I the best possible value from the companies he represents.

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Angela Roberts

Oct 31, 2025 at 5:16 pm UTC

Professional, attentive, sincere, has the clients best interest. Always a pleasure to work with. 100%

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Debbie Finberg

Oct 27, 2025 at 1:19 pm UTC

Jake is very helpful. He returns calls promptly. We highly recommend him for your insurance needs.

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Wayne L Winquist

Oct 25, 2025 at 4:29 pm UTC

Jake has consistently offered us good ideas for our Medicare supplement insurance, drug coverage, and eye care. He cares about his clients. I was served by his father before him, and he is continuing his father's tradition of excellent and caring service.

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Ira Kastenberg

Oct 22, 2025 at 9:34 pm UTC

Helpful, reliable, knowledgeable.

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Jode Rettschlag

Oct 18, 2025 at 9:13 pm UTC

Highly recommend Jake as he is knowledgeable, trustworthy and responds quickly. Have been working with Jack and now Jake for nearly 15 years and can't thank them enough for their guidance all these years. Thank You

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Deborah Wolter Rohloff

Oct 18, 2025 at 1:11 am UTC

Always explains everything clearly, has answers to all my questions, I’m always feeling better after I talk with him!

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Ann Demers Salzman

Oct 17, 2025 at 11:13 pm UTC

I have been doing business with Jake for a few years now and HIGHLY recommend him. He explains things very well and is very patient when answering any questions I might have. He is readily available, too. I feel so lucky having him as my agent.

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