Dayna Schafer, CMIP®

“I want each person I work with to feel confident that I heard what their medical and financial needs are as it relates to their health insurance. That’s the job.”

– Dayna Schafer, Founder

Her career began in Human Resources, where she spent years working alongside employees navigating complex benefit decisions, often under pressure, and without the guidance they needed. She saw what happened when people ended up in plans that didn’t fit their situation: the financial consequences, the stress, the confusion that came from a decision made without the right support.

When she moved into insurance and began specializing in Medicare, it was a natural continuation of work she had already been doing for years. The questions were the same. The stakes were the same. The need for a trustworthy advisor who would actually listen was exactly the same.

In 2001, she founded Bayside Health Benefits on that foundation, starting with employer health plans in the greater St. Petersburg area, then following the healthcare system through the Affordable Care Act and into Medicare. More than two decades later, the practice she built has stayed true to one principle: every client deserves to feel genuinely heard, and Dayna is more than determined to be the one to listen and find what serves them best.

Dayna holds the Certified Medicare Insurance Planner™ designation, administered by the Society of Medicare Planners™, a credentialing organization for experienced Medicare insurance professionals who meet specific standards for knowledge, experience, and ethics.

To qualify, agents must meet experience requirements, complete annual Medicare Advantage/PDP certification, remain in good standing with their resident state insurance department, and commit to ongoing ethical standards.

For Dayna, the credential reflects the same standard she brings to every conversation: listen first, explain clearly, and help each client feel confident in their choice.

Today, as a Certified Medicare Insurance Planner™, Dayna works one-on-one with each client to understand their doctors, prescriptions, and budget, and match them to the plan that truly fits, not just for today, but for the years ahead. She represents 11 leading insurance carriers, knows the local doctors, pharmacies, and senior resources across Citrus, Hernando, Pasco, Polk, and Pinellas Counties, and considers her work ongoing long after enrollment is complete.

Medicare changes every year. Carriers adjust their plan structures, their networks, and their pricing. Your health situation changes too. Dayna conducts annual plan reviews with her clients and stays reachable when life events, new prescriptions, or changes in coverage require a closer look.

The goal is not to enroll you in a Medicare plan, but to be your trusted, dependable Medicare advisor for the years ahead.

Dayna offers free one-on-one consultations with no obligation to enroll in anything. Get your questions answered and needs addressed with an advisor who’s here for you, like family.

Call (352) 999-2727 | TTY 711

What is the Certified Medicare Insurance Planner™ (CMIP®) designation?

The Certified Medicare Insurance Planner™ designation is an independent professional certification administered by a credentialing organization for experienced Medicare insurance professionals who meet specific standards for knowledge, experience, and ethics.

How did Dayna Schafer get started in Medicare planning?

Dayna’s career began in Human Resources, where she spent years helping employees navigate complex benefit decisions. She saw the consequences of people ending up in plans that didn’t fit their situations, and that experience shaped her decision to specialize in Medicare. She founded Bayside Health Benefits in 2001 and has served Central Florida Medicare beneficiaries ever since.

What types of Medicare plans does Dayna help clients compare?

Dayna works with 11 financially stable insurance carriers, which allows her to compare Medicare Supplement (Medigap) plans, Medicare Advantage plans, and prescription drug coverage across the full range available in your area. She recommends based on your specific situation, not on any carrier preference or commission structure.

Does Dayna offer annual Medicare plan reviews?

Yes. Annual plan reviews are one of the most valuable services Dayna provides. Medicare plans change their structures, networks, and pricing every year, and the plan that fit your situation previously may not be the best option today. Dayna recommends a review before each Annual Enrollment Period, which runs from October 15 through December 7.

How can I schedule an appointment with Dayna Schafer?

Call Bayside Health Benefits at (352) 999-2727 (TTY 711) to schedule a free one-on-one consultation with Dayna. The consultation is at no cost and carries no obligation to enroll in any plan.