Meet Our Agents
Our experts can help walk you through your options and compare the top carriers and plans available.
MRS Insurance is growing! We have agents throughout the Tampa Bay Area in Florida to serve you, and we are licensed in 19 states and expanding.
Our Founders
Profile
Sherry Gillard’s role as principal of MRS Insurance is marked by an impressive track record in the insurance industry, reflecting her dedication and expertise. Her journey began in 1997 on the variable annuity sales desk with Raymond James & Associates in St. Petersburg, Florida. Her passion for the industry led her to Chicago, where she served as an inside wholesaler with Scudder Investments in 2000. Following the events of 9/11, Sherry returned to her roots in Niagara Falls, New York, and became a variable annuity Regional VP with US Allianz, showcasing her adaptability and resilience. Her commitment to her craft ultimately brought her back to Tampa Bay in 2008, where she served as a marketing manager before joining the family business in 2018.
As the principal of MRS Insurance, Sherry brings a wealth of experience to her clients. She is not only dedicated to providing top-notch service but also actively trains new agents and contributes to building the business. Beyond her professional life, Sherry is a champion of pro-life initiatives, anti-human trafficking efforts, and support for missionaries serving orphans and widows.
When she’s not working, Sherry’s diverse interests shine. She finds solace in the mountains and the serenity of the beaches, loves camping and traveling, has a flair for cooking, enjoys gardening, spending time with family, friends and her dog, Princess. Her multifaceted experiences and commitment to both her professional and personal passions are what make Sherry an integral part of the MRS Insurance family. Together, we strive to offer personalized service and a shared commitment to the values we hold dear.
Profile
Mary Martin’s journey in the world of finance began after a remarkably successful 24-year career managing $500 million in assets. Her dedication and expertise led to accolades during her tenure with New York Life, Raymond James, and Prudential. Notably, in her role as Vice President, Investments for 20 years, Mary’s exceptional skills and commitment earned her numerous prestigious awards with both Raymond James and Prudential, cementing her reputation as a leader in the field.
In 2010, Mary returned as an independent planner and agent, focusing on asset management and Medicare needs for her clients, all while maintaining the same high standards that defined her illustrious career.
Our family-centered approach to financial planning took root when Mary was joined by her husband, Bob, and daughter, Sherry, and established MRS Insurance, with Sherry leading the way as the agency principal.
Profile
Bob Martin, a former Sergeant in the air force stationed at MacDill Air Force Base for 4 1/2 years, brought his unique perspective and skills to the family business. For many years, he managed his own music store, demonstrating his entrepreneurial spirit and a love for music.
Bob has been a licensed insurance agent in Florida since 2014, and his experience has proven invaluable to our clients.
Beyond his professional contributions, Bob is an active member of the community. He plays softball once a week and has been an avid golfer for almost 50 years. His passion for sports and music trivia adds a distinctive touch to our team, and his connection to the NBA through his grandson highlights the depth of his family ties.
Our Agents
Profile
With over 24 years of experience running a small business and a career spanning 18 years in the nursing field, I have gained invaluable insights into the challenges and rewards of the insurance industry. My nursing background has also exposed me to the financial, medical, and emotional difficulties people face when it comes to selecting life and health insurance.
The task of choosing the right insurance plan to meet individual needs and lifestyle can be overwhelming and confusing. That’s why I have made it my personal mission to guide people and ensure they avoid the pitfalls and misinformation that plague our industry.
Retirement is a new chapter in your life where you take control, and I am here to be your advocate every step of the way, helping you navigate this new occupation with confidence.
Profile
As a Southern California native, Don developed a love for the outdoors and a knack for ingenuity from an early age. His commitment to accountability and faith, instilled by his mother, guided his actions. Don’s journey led him to Loyola University of Chicago, where he met and married his bride in 1979. With 4 children and 8 grandchildren, their family thrived.
Beginning his career as the Director of a religious not-for-profit in Chicago, Don transitioned to a 30-year stint in the mail/print outsourcing industry. As an analyst, Don designed solutions that integrated people, business processes, and systems, with a focus on quality and customer care.
In 2014, after relocating to Florida, Don ventured into the health and life insurance business with Aflac, Insurance Hub, and Amac Broker Services. These experiences coalesced into his own firm, Lesher Medicare Solutions. Don focuses on matching clients with the right healthcare plans, explaining the impact on their lives both now and in the future.
Returning to his roots, Don finds fulfillment in volunteering and providing impactful solutions. His career has come full circle, from the non-profit sector to his current dedication to the well-being of his clients at Lesher Medicare Solutions.
Profile
I have been actively involved in the insurance industry since 2004, initially serving as a personal lines service representative. Over the years, I have expanded my expertise and acquired licenses in life, health, annuities, and general lines agency in 2015 and 2019 respectively. My focus and specialization are in Medicare and health insurance, particularly within the Florida region.
Family is incredibly important to me, and I have been happily married to my husband Mike for 32 years. Together, we have been blessed with two beautiful daughters and a wonderful son-in-law. Spending quality time with my loved ones, including my mom and friends, brings me great joy. When I’m not engrossed in my work or cherishing time with family, you can find me indulging in hobbies such as reading, practicing yoga, and passionately supporting the Tampa Bay Lightning as their devoted fan.
At MRS Insurance, my agency offers a comprehensive range of competitive Medicare plans to cater to your specific needs. I eagerly anticipate the opportunity to connect with you soon.
Profile
Amy is an Air Force Veteran, she served at MacDill AFB in Tampa FL. When she got out in 2005, she moved to the Florida Keys where she worked as a case manager for the Homeless for over 7 years.
In 2020, she moved with her husband and son to Pinellas County to become an insurance broker with a strong focus on helping the community with Medicare, Health & Life insurance.
Tony Calimano
Cell: (813) 786-1481
Office: (813) 553-3822 Ext: 4
Bilingual: English & Spanish
Profile
I have been involved in the healthcare industry for over 30 years.
I started my career working as a Radiographer at the prestigious Johns Hopkins Hospital Emergency Room for over 10 years.
I moved to Florida in 2001 and began working as a Medical Sales Rep in various medical sectors before switching over to the health insurance industry in 2017.
I have always found it very rewarding helping people. Transitioning from a healthcare worker to an insurance representative has been challenging yet very rewarding experience. I have found that many of my skills I developed as a healthcare worker have proven to be invaluable. My ability to communicate effectively, empathize with others, and problem-solve on the spot has allowed me to excel in the ever changing health insurance market.
Please feel free to contact me so I can help you navigate which health insurance plan you’re looking for. Lastly, I’m am bilingual if you’re looking to work with a Spanish speaking representative.
Profile
Mike has a career in education that has spanned over 30 years. This has included roles in supporting children, families and teachers. As a trained School Social Worker and Special Education Administrator, Mike has learned the importance of hard work, determination, and the value of perseverance. Overcoming obstacles builds character and resilience, teaching us discipline, which is so important in our busy lives today.
As an independent licensed insurance agent, Mike brings that same tenacity and passion to this exciting role. Building upon his roots as an educator, he will help others choose the right plan to meet their individual needs by navigating them through the confusing landscape of insurance.
When he’s not working, he loves to explore all the beauty that our state has to offer. He often embarks on adventures to small and rural towns, communities and cultural exhibits. He also enjoys hiking, camping and traveling. He is blessed to have his beautiful wife Karen by his side and two wonderful adult children to visit and spend time with.
Please Note: We do not offer every plan available in your area. Currently we represent 15+ organizations which offer 125+ plans 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.