Jason Rubin, Medicare Insurance Broker
Jason Rubin
Jason Rubin Insurance Services LLC
Medicare Broker Licensed in CA, AK, AL, AZ, CO, FL, GA, HI, IA, ID, IL, KY, MA, MD, ME, MI, MN, MT, NE, NJ, NM, NV, NY, OH, OR, PA, SC, SD, TN, TX, UT, VA, WA, WI, WV and WY
19+ Years of Experience
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Woodland Hills, CA
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About Me
Where Quality Healthcare Meets Compassion
Located in Woodland Hills, CA, we have been providing Medicare Insurance plans to individuals 65 and over for the past 15 years. Our company offers a range of services, including Medicare Supplement, Medicare Advantage, Part D Prescription Drug Plans, Dental health insurance, and more.
With years of experience in the Medicare industry, Jason has assisted numerous individuals in navigating the complexities of Medicare. His unwavering commitment to offering simplified Medicare plans to those who need them is a testament to his passion for helping people.
So, when you choose Jason Rubin Insurance Services, you can rest assured that you are getting personalized, professional service from a Medicare specialist who genuinely cares about your health and needs.
Our commitment to providing a personal touch is what sets us apart. Being a smaller agency allows us to devote ample time to addressing your needs and delivering exceptional service. Given the perplexity and confusion surrounding the Medicare system, we hold transparency and honesty as our company's foundation. By doing so, we strive to alleviate any confusion and offer a clear path forward for our clients.
As a family-owned company located in California, we understand the importance of building solid relationships with our clients. We treat every client like family and are dedicated to delivering compassionate, attentive care to each and every individual we serve for Medicare in Woodland Hills CA.
As you approach your mid-60s, have you found yourself pondering questions such as "What does Medicare Advantage really entail?”, "When is the optimal time to enroll in Medicare?”, “What are the costs associated with Medicare?" and "What exactly do the four parts of Medicare entail?" If so, rest assured that you are not alone in your curiosity.
We help you compare plans and understand the costs and benefits of each option while also offering resources and tools to help you make informed decisions about your healthcare insurance.
Choosing the right Medicare plan can be overwhelming, and that is what we are here to assist you with. We offer expert guidance and a variety of plans to meet your healthcare needs and budget, including traditional Medicare, Medicare Advantage, and Medicare Supplement plans, as well as Medicare Prescription Drug Plans.
Services:
Medicare Supplement, Part D, and Medicare Advantage plans
Long-Term Care Insurance
Life, Health and Disability Insurance
Focusing exclusively on Medicare Health Plan Options Medicare Advantage, Medicare Supplement, and Part D drug plans.
Directions to My Office
My Google Reviews
244 Total Reviews (5.0 )
September 11, 2026
It was a pleasure working with Jason. He answered my insurance questions with empathy and skill. I look forward to his help in the future.
September 10, 2026
After one chat with Jason, I am on my way to a better understanding of CA insurance and a more affordable premium. I feel calm and empowered. Thank you, Jason. Call him! You won't regret it.
September 9, 2026
I was so incredibly fortunate to find such a knowledgeable and approachable person as Jason to navigate me through the Insurance process! He was able to break everything down in digestible pieces, provide clear options, provide information on market trends, and dramatically help me to make the best choice! I highly recommend Jason!!
September 8, 2026
I truly cannot say enough wonderful things about Jason and the experience we had working with him. From the very beginning, he went above and beyond anything I would normally expect from an insurance broker. Getting our health insurance in place as quickly as possible was extremely important to us, and Jason understood that from the start. He treated our situation with a genuine sense of urgency and did everything he could to keep the process moving. What impressed me most was how available and dedicated he was. I had A LOT of questions throughout the process, and Jason patiently answered every single one. He responded to my texts after normal business hours, on weekends, and even over a holiday weekend. There were several times I expected to hear, “We’ll take care of this on the next business day,” but instead, Jason was right there helping me. I know that kind of availability isn’t something anyone should expect from their insurance broker, which is exactly why it meant so much to me. He gave up his own personal time simply because he knew how important it was to us to get our coverage handled as quickly as possible. There were moments when I was anxious about whether everything would come together in time, and Jason never made me feel like I was bothering him or asking too many questions. He was patient, reassuring, knowledgeable, and incredibly kind throughout the entire process. He explained things clearly, kept me informed, and made something that could have been extremely overwhelming feel manageable. What really stayed with me was that I never felt like we were just another application or policy number. He understood that this wasn’t simply paperwork to us. This was our health insurance, our peace of mind, and something that genuinely mattered in our lives. He treated it that way. There is a huge difference between someone who simply does their job well and someone who genuinely cares about the people they are helping. Jason is one of those rare people who manages to do both. Because of him, what started as a stressful and time-sensitive situation ended with me feeling incredibly relieved and grateful. Having someone in our corner who was willing to put in that extra effort made all the difference. Thank you for answering what probably felt like a million text messages , for your patience when I had question after question, and most importantly, for caring enough to go the extra mile for us when we really needed it. You have absolutely earned my trust and my future business. I would recommend Jason without hesitation to my friends, family, employees, or anyone looking for an insurance broker who is knowledgeable, dependable, responsive, and genuinely cares about his clients. Five stars honestly doesn’t feel like enough. ⭐️⭐️⭐️⭐️⭐️ Thank you, Jason. We are incredibly grateful for everything you did for us.
August 26, 2026
I owe my friend Susan SO MUCH for referring me to Jason Rubin Insurance Services. I was beyond stressed out from all the e-mails and regular mail i received from EVERY company that offers Medicare. Jason made it BEYOND easy. After I signed up initially with Social Security - I called Jason and literally ONE phone call - he explained EVERYTHING and took care of everything - and within minutes i was done. The next day i got an e-mail confirming my approval and here we are 6 weeks out before it's even effective - and i'm ALL signed up and ready to go. Thanks Jason - I will tell ALL my old friends to go through YOU.
Q&A with Jason Rubin
Should I sign my parents up for Medicare?
Answer: Here are the key things to consider:
1. Are they 65 or older?
• If yes and not enrolled yet: They generally should enroll during their Initial Enrollment Period (IEP) – the 7‑month window starting 3 months before the month they turn 65 and ending 3 months after.
• If already over 65 and not enrolled: This can be more urgent; they may face late enrollment penalties or gaps in coverage if they wait longer.
2. Do they have other coverage now?
• If they’re still working (or covered under a working spouse’s employer plan) and that plan is from a large employer (20+ employees), they may be able to delay some parts of Medicare without penalty.
• If their only coverage is individual insurance, COBRA, retiree coverage, or a small‑employer plan, they usually should enroll in Medicare at 65 to avoid penalties and ensure primary coverage.
3. Which parts of Medicare are we talking about?
• Part A (Hospital): Often premium‑free if they worked enough years; most people should enroll at 65 unless there’s a special case (e.g., they contribute to an HSA and want to keep doing so).
• Part B (Medical): Has a monthly premium; delaying it without qualifying employer coverage can cause lifetime penalties and delayed access to doctors/ outpatient care.
• Part D (Drugs) or a Medicare Advantage plan (Part C) or Medigap may be needed depending on their health and prescriptions.
4. Penalties and costs if you wait too long
• Part B penalty: 10% higher premium for each full 12 months they could’ve had Part B but didn’t, often for life.
• Part D penalty: 1% of the “national base premium” per month they go without creditable drug coverage, also typically for life.
5. How to actually help them sign up
• Create or use their my Social Security account at ssa.gov.
• Enroll in Medicare Part A and B through Social Security (online, phone, or in person).
• Then decide:
• Original Medicare (A & B) + Part D + optional Medigap, or
• Medicare Advantage (Part C) that bundles A, B, often D, and extras.
I'm taking a brand-name medication that doesn't have a generic version. How can I find a Medicare Part D plan that will cover it at a reasonable cost?
Answer: To find a Medicare Part D plan covering your brand-name medication, use the Medicare Plan Finder on Medicare.gov and input your medication, dosage, and preferred pharmacies to compare plans and costs.
I've been on disability for years and am about to turn 65. Do I automatically get Medicare because I'm on Social Security, or do I need to do something?
Answer: Yes, if you're receiving Social Security disability benefits and are about to turn 65, you'll be automatically enrolled in Medicare Part A and Part B. You don't need to do anything to enroll, but you can choose to delay Part B if you have other creditable coverage.
Why do doctors not like Medicare Advantage plans?
Answer: Doctors dislike Medicare Advantage plans due to administrative burdens, low reimbursement rates, and frequent denials of care, which impact their practice and patient care.
Can I backdate my Medicare enrollment if I missed my initial window due to a medical emergency?
Answer: While Medicare doesn't typically allow backdating enrollment due to a medical emergency, you might qualify for a Special Enrollment Period (SEP) to enroll outside your initial window, potentially avoiding penalties.
Does Medicare cover cancer screenings, and how often can I get them?
Answer: Yes, Medicare covers various cancer screenings, primarily through Part B, and the frequency of these screenings depends on the type of cancer and individual risk factors.
How is Medicare Advantage expected to evolve in the future?
Answer: It's hard to predict the future of Medicare Advantage. Many hospitals and doctors leave the system every year. I think we still need to wait and see what happens. I would pay close attention to our current administration and see if CMS chooses to make any changes in the foreseeable future.
Can you describe a time when you helped a client navigate a complex Medicare issue?
Answer: I assisted an individual last week who was new to Medicare and had no idea the difference between original Medicare with a supplemental plan or a Medicare Advantage plan. After conducting a thorough needs analysis, it was determined that most of his doctors accept Orignal Medicare only. I proceeded to enroll the individual in a Medicare supplement plan along with a Part D drug plan.
What is the biggest mistake seniors make when enrolling in Medicare?
Answer: Not knowing about the fee for Medicare Part B or the potential of paying for IRMAA. I feel the public is not informed about this topic, and it becomes a big surprise when they receive the statement in the mail.