Woof! I just went through this.
First of all, my former employer offered Via Benefits, but I chose not to even talk to them. They have a bunch of complaints online, which gave me pause. And they had only two Medigap plans in my zipcode, while Medicare.gov had @25 plans, and I found less expensive plans online very easily. YMMV.
Medicare.gov is useful for a bunch of info, but it doesn't try to tell you everything, so google is your friend. Do read up at medicare.gov about the basics of how Medicare works, and how Medicare Advantage vs Medigap works.
Medicare.gov will give you a list of what plans are available in your zip code, for MedicareAdvanatge, Medigap, and Rx Drug Plans, and the list has links to those insurance companies. It's then up to you to check out each of those plans on your own.
They seem to want you to choose MedicareAdvanatge. If you click on the New to Medicare link on the medicare.gov website (I might have gotten that wording wrong), they only list MedicareAdvantage Plans and Rx Drug Plans. If you want to see Medigap plans, look for a link labeled something like "Find health and drug plans." And I see they have just revamped their website. So my wording on links should be taken with a grain of salt.
First of all, whatever else you decide about talking to Via Benefits or other such firm, you must sign up for Medicare Parts A and B before signing up for anything else. Part A is for hospitalization. Part B is for doctor's visits. If you delay signing up for this, you will pay a higher premium forever. But if you sign up during your Initial Enrollment Period, you will pay the usual premium.
Your Initial Enrollment Period is a 7 month period, including the three months before the month you turn 65, the month you turn 65, and the three months after you turn 65.
Medicare.gov will tell you that in order to sign up for Medicare you must first create a mySocialSecurity account at ssa.gov. Good luck with that; I was completely unable to do so. Partly because I had a security freeze on my Equifax account (SSA uses Equifqax to verify your identity), and partly because SSA's website does not give a clue as to the format they require for things like your SSN (include dashes or not?) and your phone number (home phone or cell? parens around the area code?). Then they lock you out for 24 hours if you don't get it right in three tries.
Tip 1: Medicare.gov says that you must create a mySocialSecurity account, or at least try to. So after becoming utterly frustrated, I called them. It took a while waiting till they had a live person answer, then it took maybe 10 minutes to run through some questions they had, and then they scheduled me for a phone call to enroll in Medicare. It might be a couple of months to get a phone appointment or an in-person appointment at your local SSA office, but I was lucky and got a phone appointment for 3 days after that first call. Then on the appointment call (they call you at home at a scheduled time), it took about 10 minutes and that was it - I was enrolled in Medicare Parts A and B.
Tip 2: You don't actually have to have a mySocialSecurity account if you don't want it. You can enroll in Medicare without it.
You don't actually have to wait till you're enrolled in Medicare to check out Medicare.gov and the plans in your area. Start reading up now to get familiar with the jargon. Look at the lists of insurance companies from Medicare.gov that sell medicare policies in your area, and check them out.
Along with Medicare Parts A and B, you will probably need either MedicareAdvanatage or a Medigap policy plus a Part D Rx Drug plan. Some MedicareAdvanatge palsn include Rx drugs; some do not - in which case you will need a separate Rx plan.
MedicareAdvantage plans are sort of like HMOs; you usually have to see doctors in their network to get any benefits at all. But there are Advantage plans that are HMOs, some that are blends of HMO with POS or PPO. You will usually pay a lower premium for an Advantage plan than for a Medigap plan.
Medigap plans are secondary insurance plans, where Medicare is your primary insurer. You do not have to see a doctor in your Medigap plan's network. With Medigap, and Medicare, you can see any doctor you want, as long as they take Medicare.
Note: You do need to check if the doctor you want to see takes Medicare - not all of them do. If they do, then they must also take your Medigap as well.
There are a bunch of different Medigap plans, all approved by Medicare. They are designated by letters from A to N, and a plan of any letter will be identical anywhere in the country in terms of what it must cover. Medicare.gov has a table of all of the Medigap plans, showing exactly what each plan covers. Check that table out, decide which letter plan works for you, and then you can focus on which companies offer that plan.
Medicare imposes requirements on the Medigap plans as to the max deductible. A couple of the plans have a max OOP, but most do not.
Rx Drug Plans - Again, Medicare imposes requirements on the insurance companies as to the max deductible. The trick is to figure out if the company covers the drugs you take, and if so, how much you will pay for them in copay or coinsurance. The insurance companies can set up their own tiers of drug types, with different copay/coinsurance for each tier. This can really affect how much you pay during the year. The same drug can be in different tiers at different companies, making the cost you pay very different. Also, different insurance companies will have different "preferred" vs "standard" pharmacies, with different copay/coinsurance depending on where you get your Rx filled.
Medicare.gov supposedly has a way you can check your Rxs to see which company would be more cost-effective for you. Take that with a grain of salt. Each insurance company will also estimate your costs, anonymously online, if you put in your drug info.
Ok, well, I hope you are not already exhausted just reading this.
Good luck!
IsoFIRE