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The Story Behind Cherry Insurance

Rooted in Chicago but serving 31+ states, our mission is to guide every Medicare client with care, clarity, and the kind of support you’d expect from family.

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Company Story

How It All Began

Cynthia Cherry started her insurance career in 1995, but her path into Medicare guidance truly began at home. She cared for her mother through leukemia and later supported her aunt and uncle through their own health challenges — experiences that shaped her belief that every client deserves patience, compassion, and honesty. Over time, she saw how overwhelming Medicare could feel for families and realized there was a need for someone who could break things down simply and support people through real-life decisions. Built on the belief that service starts with people, not transactions, her work has always been grounded in that personal commitment.

Mission Highlight

Real people, real care, real experience

Our family is proud to serve clients across North Carolina and beyond, continuing Ken’s vision of providing clear, trustworthy Medicare advice for every stage of life.

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Ken Parson

Founder & Lead Medicare Advisor

Meet Ken
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Lydia Parson

Medicare Specialist

Meet Lydia
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Gil Parson

Medicare Advisor

Meet Gil
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Mission

Our mission is to help seniors and families make confident Medicare decisions through clear guidance, genuine care, and straightforward support.

Values

What We Stand For

  • Integrity

    We prioritize honesty in every conversation, helping clients compare Medicare options with clarity and confidence. We want you to feel informed, supported, and never pressured.

  • Compassion

    Cynthia’s caregiving background guides the way she works. Every client interaction is grounded in patience, empathy, and respect.

  • Expertise

    With nearly three decades in the insurance field — and more than 10 focused entirely on Medicare — we bring deep knowledge to every plan comparison. We stay up to date with carriers, networks, and changes that matter to Illinois residents.

  • Community

    After serving seniors across Chicago neighborhoods and Illinois communities for years, we understand the Medicare challenges local families face. Our goal is to be a steady, trustworthy resource.

Community

Proudly Serving 31+ States

For clients across Chicago, the suburbs, and throughout Illinois, we provide Medicare guidance shaped by real experience and unwavering dedication. Cynthia is licensed in 31 states, partners directly with major carriers like Aetna, Humana, Cigna/HealthSpring, and UnitedHealthcare, and offers unbiased comparisons for a wide range of Medicare needs. Many clients share that they appreciate her patient, down-to-earth style and the feeling that someone is finally “in their corner” when navigating Medicare choices. Whether meeting remotely or in person in the Chicago area, the goal is always the same: support that feels personal and trustworthy.