New to Medicare
Understand enrollment timing, Parts A and B, and how supplemental, Advantage, and Part D coverage fit together.
Independent Medicare education and enrollment support
Personal Medicare guidance across 36 licensed states. From our California neighbors to clients across the country, we help you understand your options and plan your next steps.
Medicare Annual Enrollment
October 15–December 7
Annual Enrollment is a chance to consider changes to Medicare Advantage and prescription drug coverage for the coming year. An appointment may help when you are considering your overall Medicare coverage.
Start with a quick next-step check. No contact details needed.
How We Help
Understand enrollment timing, Parts A and B, and how supplemental, Advantage, and Part D coverage fit together.
Compare flexibility, networks, premiums, referrals, out-of-pocket costs, and travel considerations without pressure.
When we help you plan for Medicare, we also review prescription drug coverage so your doctors, medications, pharmacies, and overall coverage fit together.
In our clients' words
It was a great experience working with Sam to help me transition to Medicare and simplify the process of everything. Sam was easy and straightforward…
Sam and Sarah have been extremely helpful with the Medicare process. It is a new road for me and could have been confusing. Sam made…
My wife and I had no idea how to proceed with setting her up with Medicare but Sam made everything simple for us to understand…
Quick response and excelent advice! Saved us a lot of cash!
Sam’s experience maneuvering through the gauntlet of the social security and Medicare systems to get me signed up was fun to witness . Sam also…
Sam is the consummate professional. Very knowledgeable in all things related to Medicare, I rely on Sam for answers to every question. Sam is always…
Sam was a Godsend for Me coming from a Construction background and not being very tech savvy. He was so helpful and even helped with…
Sam Olson Insurance Services is the Best! Very professional and personable. Sometimes when you're dealing with caring for ailing family member, and health insurance and…
Very professional experience working with Sam. He helped my navigate through the complicated system of Insurance and found the best option my me. Polite, patient…
Sam has been knowledgeable with both Medicare and the supplement plan. I was given Sam’s information by a coworker who was very pleased and so…
Great customer service. Always returned calls and questions on the same day. We appreciated all the guidance that was given to us.
Sam really helped my mom save on her medicare supplement and prescription plan. I plan to use him in a few years when I hit…
Sam and his assistant were extremely helpful and professional. Sam was knowledgeable in the plan I wanted and helpful in providing the change. I would…
Personable and expedient. Sam knows the answers or where to find them. He made the whole process straightforward.
So grateful being introduced to Sam by a mutual friend who highlyrecommended him. Sam worked very hard getting me back ontrack with my previous insurance…
It was a pleasure to work with Sam Olson to get a Medicare Supplement Insurance policy. He is very knowledgeable and professional. In addition, he…
Professional, timely and helpful making the transition to Medicare seamless. Highly recommend using Sam
Sam has been a great advisor. He is well versed in options available and made recommendations when I asked for them. He is extremely responsive…
Sam was a true pro. very knowable on various options and what would be the best options for me. Great follow through on meetings and…
Working with Sam Olson was an outstanding experience. He took what could have been a confusing and overwhelming Medicare process and made it clear, manageable,…
Excellent customer service! Sam Olson made the transition to Medicare seamless, and went above and beyond to help us with our enrollment. Very professional and…
I found Sam Olson to be professional, helpful, and he saved me money
Sam guided our selection of health insurance options. He was concerned with both quality and cost. We saved money and found him knowledgeable and responsive.…
I enjoyed meeting with Sam and he was very helpful. He explained all my options, made recommendations, and took care of all the details. I…
Sam is very knowledgeable and provides great service.
I appreciate the way Sam helped us navigate the next phase of life for us. He presented all the options, allowing us to choose what…
Excellent service. Sam is very attentive and easy to work with. I would definitely refer my friends to him. Thanks Sam
Sam was amazingly helpful throughout the entire process of helping me get set up with Medicare. His knowledge of the system is tremendous. Sam takes…
Great Experience transitioning to Medicare with Sam's guidance and assistance. Highly recommended! 🤙🏼
The best and down to earth guy and very helpful and quick response at every phone call or message Sam is a very nice guy…
Thanks to Sam Olson for making the Medicare enrollment process so much easier than doing it on our own. My wife and I felt we…
Sam was very easy to talk to, explained all of our options, and helped us chose the right plan for us. Sam continues to educate…
Mr. Olson in my humble opinion has done an excellent job guiding me through signing up for Medicare supplements. Had some issues with the Medicare…
Sam Olson has been pivotal in providing step by step assistance with Social Security Medicare and Social Security Disability for both my wife and I,…
I would highly recommend using Sam Olson Insurance Services. Sam's knowledge of how Medicare insurance works along with making sure you are on the right…
I was referred to Sam by a friend, who raved about him, and his “ seamless process”.…
I’ve sat in a couple Health Insurance offices trying to find health insurance that fits within my budget. But most importantly for me is the…
I recently had to step in and help "MOM" with some insurance issues. Sam is a life saver! Helped me get everything straightened out and…
I am so grateful I found Sam when I unexpectedly lost my medical insurance. I called Sam in a panic and he met with me…
informative and helpful
I was very impressed with Sam’s knowledge of insurance, as well as his timely response to my phone calls and questions! In addition, he is…
Excellent service. Sam was very thorough in the entire Medicare process. (and patient with a few of my mistakes) the followup recap email was much…
Sam is awesome. He's helped several of my clients, he's our go to resource!
Extremely thorough and detail oriented!
Sam has been an asset to Lifeworks and to our clients. He comes to the meetings prepared, with great explanations and educates our clients in…
Sam helped my parents get signed up for Medicare. He explained their options thoroughly and helped them make the best choice for them. Highly recommend…
Sam Olson is the best family health insurance agent. Sam thoroughly explains your options. He goes out of his way to make sure you get…
We have been lucky enough to both work with Sam and his company and also witness firsthand the amazing care they bring to their work…
Sam was a lifesaver for my husband & I when it was time for us to apply for Social Security & Medicare! He spent a…
Sam and his team are fantastic - highly recommend!
Sam has a wealth of knowledge in the insurance space. He is honest and has the heart of an educator to help his clients understand…
Sam has helped me and several of my clients transition from Employer coverage to marketplace insurance as well as transition to Medicare when the timing…
I was so fortunate that my dear friend Patricio Quiñones introduced me to Sam Olson. When I share with my friend that I was so…
I'm gonna recommend Sam's services from a different perspective than most people who are leaving a review.…
The world of health insurance ranges from confusing to downright inscrutable. A good broker can help you sort it out, and will be there later…
We were recommended to Sam from a friend who just went through signing up for Medicare. And this was the best recommendation for this kind…
I wasn't sure what to expect at this meeting. I was extremely satisfied meeting with Sam , he was very personable very knowledgeable with everything…
My wife and I highly recommend Sam Olsen, he was extremely helpful with finalizing and signing us up for Medicare Part B and picking a…
Sam was a tremendous help and walked me through every step of the process. He's incredibly easy to talk to and most importantly, easy to…
My process with Sam Olson, has been seamless!! This entire Medicare, Social Security, Insurance process can be so intimating and working with Sam has made…
Good source for healthcare insurance.
Sam Olson took care of everything regarding Medicare including education and adequately providing answers to questions and provide guidance.
Sam helped me navigate Covered California and get the best plan for my needs. Great Job Sam!
Absolutely the Best!! Sam knows his job and does it well. He is always willing to spend some time resolving the issue at hand. Lets…
This process can be very confusing and overwhelming especially if it is your first time through it.Sam spent a lot of time upfront with our…
Your knowledge and assistance is greatly appreciated.
I can't think of a single negative working with Sam Olson. It was enjoyable, productive and his knowledge and expertise resulted in financial savings that…
Mr. Sam Olson is a specialized agent helping Medicare patients find the right co- insurance to offset the limits in Medicare. He is knowledgeable, very…
Really understood the medicare insurance system. Made signing up easy and Sam followed through on all items that needed to be completed. Highly recommended.
Sam demonstrates a level of professionalism and expertise that sets him apart in the industry. Sam is not only responsive to my inquiries but also…
Sam laid out options for three plans, no pressure to make a decision on the same day. When I chose the best option for me…
Sam Olsen was highly recommended to me for help with my Medicare dilemma, and did not disappoint. Sam went above and beyond to ensure I…
Sam was very helpful in facilitating me changing my health insurance plan. I was anxious about doing it but Sam smoothed the way. He's very…
Sam was extremely helpful and knowledgeable and had excellent insights into recommended policy carriers. He helped navigate the confusing Medicare options and processes and explained…
Sam Olson has an approach and a manner of speaking to you that instantly puts you at ease. He's an excellent communicator, easy to work…
Navigating Medicare felt like trying to decipher an ancient code—until I met Sam. He is simply exceptional. My insurance needs are complex, and the overwhelming…
A friend of mine introduce me to Sam Olson for insurance coverage explanation, I'm very pleased to meet with Sam, he takes his time to…
When moving to a new home, there are alot of things to remember. When moving to a new state, a whole different level of actions…
Sam has been a trusted advisor to my family in navigating Medicare. Prior to his assistance, I was struggling to get the right coverage for…
I can't say enough on how satisfied I am with Sam's customer service. He helped me set up my husband on Medicare and found him…
Sam was patient and explained to me all the options available to me. He walked me through both the benefits and the hazards of the…
Sam was very professional. He was so helpful in setting me and my husband up for Medicare which can be very confusing. He was willing…
Sam definitely seems to always take his job seriously and performs it in a professional manner. When I send a note via text or email,…
I know Sam from a professional networking group and have had the pleasure of learning about the quality of service he provides. He has helped…
We have an employee turning 65 - and needed help navigating the throes of Social Security and Medicare. We found Sam through a referral -…
Sam is an incredible resource for our family. Very professional, knowledgeable and responsive.
I was completely taken care of by Sam, he knows the healthcare system extremely well, I fully trust his expertise and my healthcare is in…
Sam has helped me a lot without any benefit to him. Hopefully he will remain my friend and future agent. Thank You kind sir.
Sam Olson is an expert Healthcare Broker. A friend referred him to me because he had made her recent transition to a new provider utterly…
Sam is the best insurance guy you will meet. He specializes in health care and medicare. He takes the time to really get to know…
Thoughtful, knowledgeable individual. I recommend Sam and his services explicitly.
Sam has been a big help with finding the best Medicare supplement plans to fit our needs.I highly recommend his business.JS
Mr. Olson was very helpful in explaining the insurance and the process. He was also very knowledgeable in how MediCare and the associated insurances work…
Sam is thoughtful, thorough, and an excellent advisor. He prepares for his consultations and provides terrific client service.
Sam has a lot of knowledge about healthcare insurance. He's quick to respond to questions and helped us set up a great policy for my…
I've had a great experience working with Sam in applying for Medicare and sifting through the various plans that you need to choose from, which…
Sam has been very knowledgeable and helpful for navigating my insurance benefits and choosing which plans suit my needs best.
Navigating the transition from my husband's employer insurance to original medicare with a supplement plan and prescription coverage was utterly daunting. A friend recommended Sam…
Sam is very knowledgeable in all the MediGap Plans...medical, dental, vision, and drug. More importantly he makes absolutely sure each plan is tailored to your…
Friendly, informative, attentive service and info with Sam. Made switching Medicare Supplemental accounts easy.
Sam is very personable and friendly. He is very dedicated to his profession, and he does his job quite well.
It was easy, pleasant, and saved me money.
Sam is the best! Very knowledgeable about the industry and different policies. Was able to answer all of my questions and was very efficient in…
Sam is very helpful and so patient! He really knows his business.
Sam is very knowledgeable on all aspects of Medicare. He asked a lot of questions, and listened to all our answers. Based on our answers,…
Sam was helpful and efficient. He made our family’s experience setting up new policies seamless and easy. Would definitely use him again for any future…
Sam was SO helpful and kind while I figured out my insurance options!!! Great communicator and super responsive. Couldn’t recommend more!
I am so grateful for meeting Sam as he has explained to me how Medicare works and also the differences between supplemental insurance plans for…
Ever since being referred to Sam, I have been referring him to others! Sam is so professional and yet so personable. Sam knew exactly what…
Sam knows the Medicare program as well as anyone I’ve spoken with! Trusting in his recommendations is what’s in your best interest!
I cannot say enough great things about Sam Olson. What I thought was a total maze getting set up with retiring Sam set my mind…
Sam is extremely knowledgeable. With his help we saved $300 per month in health insurance. Sam was great and I'd highly recommend him.
If I could give Sam 101 stars, I would. After having had a Medicare Advantage plan for 20 years, I finally needed major medical care,…
Sam is a really easy to work with guy with a great personality and professionalism that is rare these days. He walked us through everything…
I tried navigating the sign up process for over a month. It is so difficult and confusing I got absolutely nowhere. I met with Sam,…
So far, so good! Sam is a great listener and very responsive to calls and emails. Listening skills are really important to me as too…
Thank you so much. 😊
I heard horror stories from other people who were transitioning to Medicare and supplemental policies. One friend told me it took him 6 weeks to…
Hello there! I have to be honest, I have not used Sam for insurance needs. But I was his client at a previous career/job. And…
Sam helped my husband and I navigate the Medicare system which can be a tad overwhelming. He is extremely knowledgeable, professional, and dependable. Would highly…
Sam was so helpful getting me signed up for Medicare and the supplemental insurance. He was very responsive to my questions with very quick replies.…
I called Sam to help me set up a prescription drug plan for my older brother. Sam was great! He set up a video conference…
Sam Olson provided the details that I needed in order to make an informed decision regarding a Medicare Supplement policy. He further assisted in the…
Excellent...
He did a great job speaking to our group. He had a lot of knowledge and helped with all our questions.
Sam Olsen provided a very informative seminar to the residents of a senior housing community in Clovis, California. Not only was he knowledgeable, but he…
Recently I moved outside the Kaiser service area and had to find my way through the maze of web pages to find a Medigap plan…
Sam went the extra mile for us. Great to work with.
Sam is very knowledgeable and very personable. He explained the intricacies of Medicare supplemental plans and drug plans clearly. Because he represents multiple insurance companies,…
My husband and I met with Sam on several occasions to discuss our current healthcare coverage needs. In addition to his vast knowledge of the…
My experience with Sam Olson is profound!I was so confused and picked the wrong plan last year I needed some help.He was able to call…
Sam is extremely knowledgeable and takes the time to understand your specific situation to make sure that your insurance needs are fully met. He also…
Sam proved to be very knowledgeable regarding the Medicare process. I was pretty sure my wife and I were in a good place but Sam…
Medical insurance is complicated, and Sam has knowledge and an understanding of its complexities. I fully trust him to steer me in the right direction…
I interviewed many representative before deciding on Sam. Some were knowledgeable. Some weren't. Sam was. He supported several calls to help me understand and prepare…
Sam is highly recommended to handle your Medicare enrollment process. He provided me with more than substantial amount of information to assist me in my…
All 147 Google reviews captured October 11, 2026. Longer comments are shown as excerpts; ratings without comments are included.
Location and licensing
Our office is in Napa, California, and our clients live across 36 licensed states. We serve Napa Valley, the Bay Area, and Northern California while bringing the same care and attention to clients beyond California. Availability and plan options vary by location.
Licensing does not guarantee plan availability. Plan options vary by county, ZIP code, carrier, and plan year.
A clear comparison
Both paths can make sense. The right conversation starts with how you use care, how you feel about networks, how much flexibility matters, and what tradeoffs you are comfortable with.
Compare the two pathsStart with the basics: what Medicare covers, when to enroll, and what decisions usually come next.
Read the New to Medicare GuideA simple process
Start with a general Medicare planning conversation.
If you are preparing for an appointment, use the secure questionnaire when our office needs details before we meet.
Compare the paths that fit your timing, coverage, and preferences.
Get help with the next steps once you understand your choices.
Small local team
When you work with Sam Olson Insurance Services, you are not dealing with a call center. Our small team gets to know you and follows through, whether you live nearby or in another state where we are licensed.
Founder / Medicare Advisor
Sam founded the agency to make Medicare easier to understand, with clear explanations of Medicare Supplements, Medicare Advantage, Part D, and retirement-related Medicare decisions.
Client Service / Medicare Support
Sarah is often the first point of contact for clients and brings more than 20 years of healthcare, care coordination, and administrative support experience.
Client words
"Personable and expedient. Sam knows the answers or where to find them. He made the whole process straightforward."James R.
"Professional, timely and helpful making the transition to Medicare seamless. Highly recommend using Sam."Axel G.
Schedule a Medicare call with Sam Olson Insurance Services. If you are preparing for an appointment, use the secure questionnaire when our office asks for more detail.