About Jeffrey Werner
Based in the Boston area, Jeff Werner is an independent licensed insurance agent specializing in Medicare plans.
With 10,000 people a day turning 65, and the huge demand for information about Medicare, Jeff started OTL Benefits to help clients benefit from his unique blend of technical knowledge about Medicare, competitive knowledge about all the carriers promoting their plans, and a genuine desire to help people.
Throughout his career, Jeff has been responsible for providing health benefits for retirees, so he understands what people face when they transition to Medicare.
Jeff is a licensed insurance agent and has a national AHIP certification. He previously worked in senior level positions with national carriers, such as Blue Cross Blue Shield and Kaiser, and has also administered Union health benefit funds.
With experience in health care that spans four decades, Jeff can answer the many questions that people have as they enroll in Medicare and grapple with all the mailings from various plans.
Over the years, Jeff always made time for people who had questions. Here are some of the questions that Jeff answers every day:
Kathy from Stoneham MA called in with a common question:
“WHEN DO I SIGN UP FOR MEDICARE? WILL I HAVE TO PAY A PENALTY?”
Kathy can enroll in Medicare Parts A and B in her Initial Election Period (IEP), which is a seven month window – three months before the month in which she turns 65 or qualifies for a disability, the three months before the month in which she turns 65, and the three months after the month in which she turns 65.
Medicare imposes lifelong late enrollment penalties if Kathy delays signing up past her Initial Enrollment Period (IEP). Penalties vary:
Part B: Premium increases by 10% for each full 12-month period Kathy delays enrollment. Kathy will pay this higher premium for as long as she has Part B.
Part D (Prescription Drugs): Kathy would pay an extra 1% of the national base beneficiary premium for every month she went without creditable drug coverage. This penalty is added to thepremium for as long as she has Part D.
Bill from Dorchester MA called in with another common question:
“I AM 68 AND MY EMPLOYER INSURANCE IS ENDING. HOW DO I SIGN UP FOR MEDICARE PART B?”
Bill was 68 when he retired from his job on December 31, 2025. His health insurance with his employer also ended on the same date. Bill had signed up for Medicare Part A only when he turned 65 (in his Initial Election Period/IEP) because it was no cost to him, and he declined Part B because he continued his insurance through his employer.
In order to sign up for Part B after the IEP without paying a Late Enrollment Penalty, Bill must qualify for a Special Enrollment Period (SEP). In an initial planning meeting, Jeff Werner provided Bill with forms necessary to establish the SEP. Bill’s employer must verify that he had insurance since he turned 65. The employer must complete CMS Form L-564, REQUEST FOR EMPLOYMENT INFORMATION, and return it to Bill. Bill must also complete CMS Form 40B, APPLICATION FOR ENROLLMENT IN MEDICARE PART B (MEDICARE INSURANCE).
Bill should deliver both completed forms to his local Social Security office at least 60 days in advance of the effective date, and no sooner than 90 days in advance. In Bill’s case, he would deliver the forms no later than November 1, 2025. The forms can be hand delivered, faxed or sent Priority Mail. Social Security will confirm enrollment by regular mail and via MYSocialSecurity (if Bill has an account set up). Bill will also receive a new Medicare Card, with Part B effective date, sent by regular mail.
(NOTE – This process can be completed online through a MYSOCIALSECURITY account.)
Gary from Boston was very upset about a letter he received from Social Security about his Medicare premiums:
“WHAT IS IRMAA AND WHY DO I HAVE TO PAY SO MUCH FOR PART B?”
Gary enrolled in Medicare A and B in October of 2026, for effective date January 1, 2026. He received his confirmation letter around November 15, and then received his new Medicare card during the first week in December. He was feeling pretty good about the process when, in mid-December, he received another letter from Social Security Administration. The second paragraph contained a key sentence – “The law requires that some people pay higher premiums for their Part B (Medicare) and Part D (Prescription Drug Plan) because of their income. These increases in the premiums are called Income-Related Monthly Adjustment Amounts (IRMAA).”
Gary expected to pay the standard amount, $202.90, for Part B and then whatever Part D premium offered by the insurer. Reading further, he saw his 2024 Modified Adjusted Gross Income (MAGI) listed at $152,356. Based on this MAGI, his 2026 Part B premium would be $405.80, and $37.50 would be added to his Part D premium.
In the initial client meeting with Gary, Jeff had alerted Gary to the possible impact of IRMAA. Jeff advised Gary that many retirees are impacted by IRMAA in their first two years of Medicare coverage, due to the two-year look-back. To resolve this issue, Jeff provided Gary with Form SSA-44 Medicare Income-Related Monthly Adjustment Amount – Life Changing Event, which can be submitted to Social Security for relief. Gary estimated that his 2026 MAGI would be approximately $85,000, which put him under the threshold for higher premiums. The happy ending was that Gary’s Part B premium for 2026 was $202.90, with no Part D premium beyond that charged by the insurer.
(Insert IRMAA chart?)
Get answers to your Medicare questions. Contact Jeff Werner today.
Call (978) 447-3737 or send an email to jeff@otlbenefits.com