Jonathan Pfisterer, Medicare Insurance Agent

About Me

Jonathan specializes in helping people understand Medicare in plain English, with an education-first, no-pressure approach. His work goes beyond simply comparing insurance plans—he closely follows CMS regulations, Medicare legislation, annual benefit changes, prescription drug rules, enrollment requirements, and the real-world impact those changes can have on Medicare beneficiaries.

Jonathan has provided Medicare education through Medicare 101 seminars at public libraries including Fox Lake, Johnsburg, and Round Lake, and has operated Medicare Help Desks within Duly Health and Care physician offices and Endeavor Health hospitals. He previously hosted monthly Medicare 101 seminars at Duly in Hoffman Estates and currently presents a monthly Medicare 101 program at Highland Park Hospital.

As an independent, multi-carrier broker, Jonathan helps clients evaluate Medicare Advantage, Medicare Supplement, Part D prescription drug coverage, and other retirement insurance options based on their individual doctors, medications, needs, and circumstances.

Jonathan works alongside his wife and business partner, Katie Pfisterer, a Registered Social Security Analyst (RSSA®). Together, they help clients look at Medicare as part of the larger retirement picture, including Social Security, retirement income considerations, long-term care planning, life insurance, and annuity solutions.

Their goal is simple: educate first, answer questions clearly, and give people the information they need to make confident decisions without sales pressure.