What we do
Medicare enrollment assistance
From your first Social Security application through your effective date, with someone who has done it several hundred times sitting on the other end of the phone.
What you get
Concrete things, not a conversation about a conversation.
Every one of these is included, and none of it is billed to you. Our compensation comes from the carrier you eventually choose — or from nowhere at all, if the right answer is to leave your coverage exactly as it is.
- Confirmation of exactly which enrollment window applies to you, and its deadlines
- Help filing for Part A and Part B, including the forms employers must sign
- A written side-by-side comparison of the realistic plan options in your county
- A doctor-by-doctor network check and a drug-by-drug formulary check
- The enrollment itself, submitted and confirmed, with your effective date verified
- A point of contact afterwards — for the card that did not arrive, the claim that got denied
How it runs
Step by step.
- 01
Work out your timeline
When you turn 65, whether you are still working, whether your employer coverage is creditable, and which of the enrollment windows that leaves you in. Getting this right prevents the late-enrollment penalties that follow people for life.
- 02
Get Parts A and B in place
Filing with Social Security, and — if you are past 65 and coming off employer coverage — obtaining the employment verification form your employer has to complete. We tell you exactly what to send and where.
- 03
Decide the structure
Original Medicare with a supplement and a Part D plan, or a Medicare Advantage plan. This is the fork in the road, and it is the one decision that is genuinely hard to reverse later. We lay out both honestly.
- 04
Choose the specific plan and enroll
Networks checked against your doctors, formularies checked against your prescriptions, out-of-pocket maximums compared. Then we submit the application and confirm the effective date with the carrier.
The mistakes we spend most of our time preventing
- Missing the Initial Enrollment Period and picking up a permanent Part B penalty
- Assuming employer coverage is creditable when it is not — check, do not assume
- Letting the six-month Medigap Open Enrollment Period lapse before deciding
- Enrolling in a plan whose network does not contain the specialist you actually rely on
- Skipping Part D because you take no medication, then paying the penalty for life
- Signing up from a television advertisement without anyone checking your drug list
What it costs you
Nothing. There is no fee, no retainer and no consulting charge. Insurance carriers pay licensed brokers a commission when someone enrolls, and that amount is built into the premium whether a broker is involved or not. Your rate is identical if you enroll on your own — you simply do it without an advocate.
That structure is why we can afford to tell you to stay where you are. If your current plan is the right one, we say so, and we are still here next October when it might not be.
Which enrollment window applies to you
Most of the difficulty in Medicare enrollment is not the paperwork — it is working out which of six windows you are actually in. Getting that wrong is what produces the penalties that follow people for life.
| Window | When | What it allows |
|---|---|---|
| Initial Enrollment Period | 7 months around your 65th birthday | Enroll in Parts A and B, choose Part C or D |
| Medigap Open Enrollment | 6 months from your Part B start date | Buy any supplement with no health questions |
| Annual Enrollment Period | October 15 – December 7 | Join, switch or drop an Advantage or Part D plan |
| Medicare Advantage Open Enrollment | January 1 – March 31 | One change, if already in an Advantage plan |
| General Enrollment Period | January 1 – March 31 | Enroll in Part B after missing your IEP |
| Special Enrollment Period | Triggered by an event | Enroll or change outside the standard windows |
What happens after you are enrolled
Enrollment takes an afternoon. The relationship is the twenty years afterwards, and that is the part most people never see advertised.
- We confirm the effective date with the carrier, not just with an enrollment screen
- We check your card arrived and shows the right dates
- We make sure your pharmacy has the new plan on file before it starts
- Every autumn we re-run your doctors and drugs against next year’s plan
- When a claim is denied or a bill looks wrong, you have a person to call
- When your life changes — a move, a diagnosis, a retirement — we re-check the fit
Frequently asked questions
Do I have to enroll in Medicare at 65 if I am still working?
It depends on the size of your employer and whether the coverage is creditable. If your employer has 20 or more employees and the plan is creditable, you can generally delay Part B without penalty and enroll later through a Special Enrollment Period. Smaller employers change the answer. This is worth a phone call, not a guess.
How long does Medicare enrollment take?
Filing for Parts A and B with Social Security typically takes a few weeks to process. Plan enrollment is faster — often processed within days — but the effective date is governed by the enrollment period rules, not by how quickly you apply. We work backwards from your effective date.
Can you help if I live outside Massachusetts?
Yes. We are based in Marlborough and licensed nationwide and work by phone, email and video with clients across the country. Tell us your ZIP code and we will confirm licensing and show you what is available where you live.
Coverage involved
The products this service touches.
-
Medicare Advantage (Part C)
Medicare Advantage (Part C) is a private plan that replaces how you receive your Part A and Part B benefits. Plans usually bundle prescription drug coverage and extras like dental and vision, often carry a $0 monthly premium, and cap your annual out-of-pocket costs — but you use a provider network and pay copays at the point of care.
About this coverage -
Medicare Supplement (Medigap)
A Medicare Supplement, or Medigap, is a private policy that pays the deductibles, copayments and coinsurance Original Medicare does not. You keep Original Medicare, see any provider in the country who accepts Medicare, need no referrals, and pay a monthly premium. Prescription drug coverage is bought separately as a Part D plan.
About this coverage -
Part D prescription drug plans
Medicare Part D is prescription drug coverage sold by private carriers, either as a standalone plan alongside Original Medicare and a Medigap policy or bundled inside a Medicare Advantage plan. Each plan has its own formulary, tiers and pharmacy network, and an annual cap on what you pay out of pocket for covered drugs.
About this coverage
Related services
Often needed at the same time.
-
Turning 65 consultations
A clear roadmap for your Initial Enrollment Period, starting six months out.
How it works -
Insurance plan comparison
Every realistic option in your county, compared against your own doctors and drugs.
How it works -
Annual coverage review
Your plan changes every January. We re-check it every October, before it costs you.
How it works