About the Agency

Medicare help from a small team that explains things clearly.

Sam Olson Insurance Services is an independent Medicare-focused agency based in Napa, California, serving Napa Valley, Northern California, and clients in multiple states where licensed.

Founder and owner

Sam founded Sam Olson Insurance Services in 2019 to make Medicare easier to understand. Based in Napa Valley, he helps clients sort through Medicare decisions in plain English, without pressure or confusion.

His work focuses on helping people compare Medicare Supplements, Medicare Advantage, Part D prescription drug plans, and retirement-related Medicare decisions. The goal is not to rush the decision. It is to make the tradeoffs clear enough that you can make an informed choice.

Sam Olson Insurance Services serves Napa Valley, Northern California, and clients in multiple states where licensed. Napa is the home base, and the agency works with people beyond California only where licensing allows.

Meet the Team

Local guidance, real follow-through.

When you work with Sam Olson Insurance Services, you are not dealing with a call center. You are working with a small, local team focused on clear guidance, follow-through, and client service.

Sam Olson

Founder / Medicare Advisor

Sam enjoys helping people take Medicare from confusing to manageable. He founded the agency in 2019 and focuses on plain-English education around Medicare Supplements, Medicare Advantage, Part D, and retirement-related Medicare choices.

Independent Medicare-focused insurance advisor based in Napa Valley.
130+ Google reviews and a strong local reputation for clear, patient guidance.
Active in the Rotary Club of North Napa.
Bachelor's degree in Business Administration from UC Berkeley Haas.
Married to Sarah Olson.

Sarah Krupa

Client Service / Medicare Support

Sarah is often the first point of contact for clients. She brings more than 20 years of healthcare experience, including client service, care coordination, and administrative support.

Former Department of Veterans Affairs Advanced Medical Support Assistant and Referral Coordinator.
Helped Veterans access specialty and urgent care and earned the Going the Extra Mile Award.
Background includes Certified Medical Assistant, caregiver, mental health technician, and American Canyon Welcome Center volunteer.
Holds a California Life and Health Insurance License.
Has lived in the Napa area for more than 15 years and enjoys time outdoors with her husband Derek, family and friends, and their dog Buddy.

Sarah wants clients to feel heard, comfortable, and confident. She believes being of service to others is an important part of living a fulfilling life.

What you can expect

Plain-English education

Medicare terms are explained in normal language so the decision feels manageable.

Independent guidance

You can compare Medicare paths without being pushed toward one type of coverage.

Local presence

The office is in Napa, with Medicare help available throughout Northern California and in multiple licensed states.

Licensed in Multiple States

Based in Napa. Licensed beyond California.

Sam Olson Insurance Services is based in Napa, California and is licensed to help clients in multiple states. This can be helpful for clients who move in retirement, split time between locations, or have family connections outside California.

The agency does not claim availability in every state, and licensing does not mean plan options are available everywhere.

Licensing does not guarantee plan availability. Plan options vary by county, ZIP code, carrier, and plan year.

U.S. map highlighting licensed states: AK, AR, AZ, CA, CO, CT, FL, GA, HI, ID, IL, IA, IN, KY, MA, MI, MN, MT, NC, NM, NV, OK, OR, PA, SC, TN, TX, UT, VA, and WA.

Have a Medicare question?

Start with a simple call. No pressure, no complicated sales pitch.

Schedule a Medicare Call