A DEDICATED MAVEN IS HERE TO HELP YOU. I pride myself on being a relational broker and not a transactional broker. I put your needs first by asking you questions regarding what is important to you with your insurance coverage. I will check your medications and doctors to be certain they take your plan. I check in with you periodically to be certain you are utilizing all of your benefits available to you which leads to your annual benefit review. Having access to shop out your insurance needs really puts YOU in the heart of the matter. At the end of the day, I am honored to be a part of your care in your Medicare journey.

As a local licensed and AHIP certified insurance broker, I serve as your Insurance Maven to provide you with easy to understand education and information you need to help you make a decision on which plan is best for your needs. ‍

I am licensed in CT, DC, FL, GA, IL, IN, KY MA, MD, ME, MI, MO, NC, NH, NJ, NY, OH, PA, RI, SC, TN, TX, UT, VA, and WA. ‍

No need to stress, Just call Jess!

Jessalyn Pito is a local, licensed broker, not a random rep in a call center. Jessalyn lives, works, and contributes to the same local communities you are a part of!

Serving the Medicare Community for over five years.






No need to stress, just call Jess!

– Jessalyn Pito

"I have been in the Insurance business in Connecticut for almost 52 years. I don’t deal in the Senior market and when my wife and I needed to select a Medicare product I was referred to Jessalyn by a fellow Insurance professional. ‍
Jessalyn was a God send. She knows the Senior Market inside and out and she helped us select Medicare Advantage Plans that fit each of our individual needs. She is easy to reach with questions and I have referred clients of mine to her confidently.
We trust Jessie and are extremely happy we are a client of hers."

"I was introduced to Jessalyn Pito by a trusted friend and financial advisor. She is very professional but very friendly. We discussed my needs and she responded with great options. She is very considerate of my time but makes sure we cover everything. ‍
I’ve been so pleased that I recommended her to my wife who has been very happy as well.
We look forward to continuing our relationship with Jessalyn as our needs change over the years. I would not hesitate to recommend Jessalyn to everyone in need of an excellent Medicare Advisor."

"Jessalyn was so helpful when I became eligible for Medicare. Her assistance in navigating the complexity of the many different plans available to me was instrumental in choosing the right plan for me.I was healthy when I applied and a short time later was diagnosed with cancer.
Her expertise in assisting me in choosing what was right for me, has allowed me to focus on treatment without worrying about the bills and copays that go with treatment.
essalyn has always been available with any questions I might have. I have highly recommended her to family and friends and she has helped them as well."



I am a licensed broker and I am dedicated to you and all of your different insurance needs:

  • Medicare Advantage Plans
  • Special Needs Plans
  • Part D Drug Plans
  • Medicare Supplement Plans
  • Life and Disability Insurance
  • Dental and Vision Plans
  • Final Expense
  • Cancer Plans
  • Travel Insurance




Jessalyn Pito - Podcast Appearances


Connecticare Aetna
Anthem Care Partners of Connecticut
Cigna Delta Dental
Humana United Healthcare

I do not offer every plan available in your area. Currently I represent 9 organizations which offer many products in your area.
Please contact Medicare.gov or 1–800–MEDICARE, or your local State Health Insurance Program to get information on all your options.