Dayna Schafer, CMIP®, Raised in Chicago, I relocated to Florida only to leave a decade of Human Resources experience behind to build a company that would bring a much needed service to our community.

I began with employer benefits in the greater St. Petersburg area. My focus has been on the growth and challenges the health insurance industry has endured. That journey took me from employer benefits to the Affordable Care Act’s implementation and now focuses mainly on Medicare.

My company and I, now a Certified Medicare Insurance Planner™, look forward to building a long-term relationship with you.

“I want each person that I work with to feel confident that I heard what their medical and financial needs are as it relates to their health insurance, and that I responded with the right medical plan for those needs. Building a relationship as their healthcare needs change is important to me and the service I provide.”

I’m originally from the Bronx, New York, and spent over a decade living in Puerto Rico. These experiences helped me become fully bilingual in English and Spanish and allowed me to connect with people from diverse backgrounds.

I spent 35 fulfilling years in education, guiding students and their families in achieving the individual needs of each student. Helping students reach their goals was one of the most rewarding parts of my career. Now, I carry that same dedication into health insurance—listening closely to ensure each person feels informed and supported in their choices, while finding the right fit for their medical and financial needs.

Since retiring from education, I’ve been helping individuals navigate their health insurance with care and clarity. I’m excited to now expand into the Medicare market as part of the Bayside Health Benefits team, continuing my commitment to serve with compassion, knowledge, and heart.