Cassandra Tripp, Medicare Insurance Agent

About Me

I’m a licensed Medicare agent proudly serving individuals and families throughout Maine, with a focus on Oxford, Androscoggin, York and Cumberland Counties. For the past five years, I’ve had the privilege of sitting across the table from seniors and their families, helping them understand Medicare and feel confident about the decisions ahead. I’m appointed with the major carriers in Maine, which allows me to take a true look at the options available and help each person find coverage that fits their individual healthcare needs, priorities, and budget.

For me, this work is about so much more than choosing a plan. It’s about education, relationships, and being someone you know you can call or text when Medicare gets confusing. My services come at no cost to you, and I believe you should understand your options before ever making a decision. I stay on top of Medicare changes, plan updates, and important deadlines so my clients don’t have to navigate it all alone.

Maine is home, and I love being a local resource in the communities I serve. When I’m not talking Medicare, you’ll probably find me at the gym, exploring our beautiful state, cheering on my favorite sports teams, or grabbing a microphone for some karaoke!

Whether you’re turning 65, retiring, already on Medicare, or simply have questions, I’m here to make Medicare a little less overwhelming and a lot easier to understand. My goal is simple: educate you, support you, and be a resource you can count on for years to come.

Get in touch with Cassandra using this form

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My Google Reviews

11 Total Reviews   (5.0 )

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Teaen Davis
August 21, 2024

I honestly can't thank Cassandra enough for all of the help she has given us over the past year. My husband became disabled & all of a sudden we were receiving information that he was on Medicare but I still had him on my employers plan. She help us navigate getting him an advantage plan so that we could take him off of my employer's plan saving us a lot of money. Then not only did she do that, we take care of my husbands grandmother's affairs, so she helped me get her on a better suitable advantage plan again saving her money. So thank you truly.

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Kathy Woodyard
August 2, 2024

Casey has everything a good agent needs. She is extremely knowledgeable, ensures she understands her clients and their needs, and clearly explains the options so her client is matched with the best option(s) available. I could no recommend her more wholeheartedly!

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Susan Brennan
August 1, 2024

Casey is a warm, engaging professional who was very thorough explaining my Medicare benefits as I soon greet my 65th year. She thoughtfully reminded me to sign up and will work with me to complete the process. Casey made this time of change easy!

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Mark Rochelle
July 25, 2024

I found Casey through a friend of mine that she worked with in the past. She came with great reviews! I met with her and she held up to her reputation. Casey was knowledgable in all areas of retirement including Medicare and even set me up with a great financial advisor to help plan out retirement. Her communication and follow up is excellent and reliable. She def goes above and beyond for her people. She gets 5 stars from me!

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Tina Maloney
July 17, 2024

Cassy is amazing!!! She is a wealth of knowledgeable about Medicare and has such a friendly personality. Not knowing anything about Medicare; where to start, what questions to ask, she had all the answers and kept it very simple to understand. I’m so grateful to her for helping me through this process. She is the best!!!!

Q&A with Cassandra Tripp

What are the reasons why I should work with a Medicare agent?

Answer: Working with a Medicare agent really saves you time, stress, and potentially a lot of money. We help you compare all your options – original Medicare, advantage plans, Medigap and drug plans – so you don’t miss out on coverage or pay more then you need to. We know the deadlines, the fine print, and how to avoid costly mistakes like late enrollment penalties. Best of all it doesn’t cost you anything extra to get expert guidance tailored to your specific health and financial needs.

How do you educate clients who are completely new to Medicare?

Answer: I keep it simple and personal – I’m a sit at the kitchen table, kind of gal. I break Medicare down into the basics; what parts A, B, C, and D actually mean, how they work together (or don’t), and what options make the most sense for your health and budget. I explain the difference between original Medicare and advantage plans in plain English, not insurance jargon. My goal is to make you feel confident in your choices and never overwhelmed.

What's the most cost-effective way for a healthy 65-year-old to structure their Medicare coverage?

Answer: The most cost-effective Medicare set up is typically Medicare (part A& B) paired with a low or zero premium Medicare advantage ( part C ) plan that includes built-in part D prescription coverage. These plans often offer low monthly costs, including dental/vision, perks, and cap your annual out-of-pocket spending. However, you’ll usually need to stay in network and pay co-pays for services as you use them. This set up typically works best if you’re healthy, have predictable medical needs, and are comfortable with provider networks and some cost sharing.

Can you explain what "creditable coverage" means and when it applies?

Answer: Credible coverage refers to health insurance that is considered as good as or better than Medicare, particularly for part B and part D. It’s most commonly relevant when someone is delaying Medicare because they’re still working and have an employer sponsored coverage. As long as that coverage is deemed credible, you can delay enrolling in Medicare without facing late enrollment penalties. When you do retire or lose that coverage, you’ll get a special enrollment period to sign up for Medicare without penalty

My income fluctuates significantly year to year from investment distributions. How can I avoid IRMAA surcharges when I have an unusually high-income year?

Answer: IRMAA surcharges are based on your income from two years prior, so a single high income year can impact future Medicare premiums. If the spike and income was due to a one time event, such as a large investment distribution, you can file form SSA – 44 to request a reduction based on a life-changing event like works stoppage or reduced income.

To help avoid surcharges in future years, my partner, Mike Secord; who is a local fiduciary, and I can help you explore investment distribution strategies tailored to keep your Medicare related income in check. We specialize in coordinating retirement income, and Medicare planning to help you keep more of what you’ve earned.

I have a family history of colon cancer. Will Medicare cover more frequent colonoscopies for someone in my situation?

Answer: Medicare will cover a colonoscopy every 24 months. You’ll need to check with your medigap plan or advantage plan to see how many more you can get.

I'm participating in a clinical trial for a new cancer treatment that uses personalized medicine based on my genetic profile. How does Medicare coverage work in this situation?

Answer: The trial could be covered by Medicare. Contact your Advantage Plan carrier or Medigap plan for more details.