Your Trusted Insurance Support

Hello and welcome to Insure With Jill. Get clear, one-on-one guidance for Medicare, life, long-term care, annuities, and supplemental coverage, tailored to your needs and budget in Southwest Florida. Together, we’ll review your options in plain language so you feel confident, informed, and well protected.

Life Insurance

Protect loved ones, cover final expenses, and support legacy wishes with life insurance aligned to your goals.


Retirement & Annuities

Create steadier retirement income with annuity and long-term care planning that supports your lifestyle and future needs.


Medicare Plans

Compare Medicare Supplement and Advantage options calmly, match your doctors and prescriptions, and avoid costly gaps or surprises.


As an independent agent, I compare multiple carriers objectively, so your coverage truly fits you.

Expect calm, one-on-one conversations where every question gets answered clearly, without pressure or rush.

I understand Southwest Florida doctors, hospitals, and retirees' priorities, so your insurance aligns with real life.

Meet the Story Behind

Discover how my locally owned, independent agency supports individuals and families across Southwest Florida with clear, down-to-earth guidance on Medicare, life insurance, and long-term financial planning. I take the time to listen, explain your options in plain language, and stay by your side year after year. To learn more about who we are and why we do this work, visit my About page next.