Medicare help from a small team that explains things clearly.
Sam Olson Insurance Services is an independent, Medicare-focused agency serving clients across 36 licensed states. From Napa Valley and the Bay Area to clients beyond California, we offer personal guidance and dependable follow-through.
Founder and owner
Sam founded Sam Olson Insurance Services in 2019 to make Medicare easier to understand. He helps clients sort through their choices with straightforward explanations, 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.
Our office is in Napa, and our clients live across 36 licensed states. We bring the same personal attention to each conversation, whether you are in Napa Valley, the Bay Area, Northern California, or another state where we are licensed.
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 clear, practical education about Medicare Supplements, Medicare Advantage, Part D, and retirement-related Medicare choices.
Independent Medicare-focused insurance advisor based in Napa Valley.
140+ 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
Clear explanations
We explain Medicare terms and coverage choices step by step, so you can make informed decisions.
Independent guidance
You can compare Medicare paths without being pushed toward one type of coverage.
Local roots, broader reach
Our California home base is part of our story. Our personal approach supports clients across 36 licensed states.
Licensed in Multiple States
One team. Guidance across 36 licensed states.
Our office is in Napa, California, but you do not need to live nearby to work with us. We help clients throughout our licensed service area, including people who move in retirement, split time between locations, or have family connections in other states.
The agency does not claim availability in every state, and licensing does not mean plan options are available everywhere.
AL
AK
AZ
AR
CA
CO
FL
GA
HI
ID
IL
IN
IA
KS
KY
LA
MA
MI
MT
NE
NV
NJ
NM
NC
OH
OK
OR
PA
SC
TN
TX
UT
VA
WA
WI
WY
Licensing does not guarantee plan availability. Plan options vary by county, ZIP code, carrier, and plan year.
Licensed stateOther state
Have a Medicare question?
Start with a simple call. No pressure, no complicated sales pitch.
