Local Agents, Local Service, Local Savings
Who We Are at Rowley Insurance
Michael Keith Rowley, Owner
Keith is an active member in our community which he has called home since 1976, attending Englewood Elementary and then Lemon Bay Junior/Senior High School. Keith joined his late father, Rex in his insurance business in 1988 and eventually purchased Rowley Insurance Agency Inc. in 2004. His family has helped thousands of families, hundreds of businesses, and countless seasonal residents with their insurance needs/questions in the Southwest Florida area and the entire state of Florida. He is a third-generation insurance agent/agency owner and is proud to continue the family vocation. When Keith is not in the office working on marketing plans and helping various community organizations, he can be found on his boat with his wife of over 36 years, Cheryl, visiting their Son , daughter in-law and grandchildren in North Carolina and keeping in touch with his youngest son as he prepares to get married. Keith is excited about being in the heart of downtown Englewood with its wonderful revitalized district and is looking forward to being a part of the revitalization.
Our History
Where it all started
Keith's Grandfather, Richard Rowley shown here with Keith (he is the youngest), his siblings and Grandmother started in the Insurance industry selling life insurance and collecting nickel, dime and quarter premiums on a weekly basis.
2nd Generation
Pictured here is Keith's late parents , Rex and Donna, in front of the family agency company car in the early 1960's.
The Team
Dana Gesmond
Alissa Edwards
Dana Gesmond
Dana joined our team in 2014, she brings many years of Insurance experience with her from Pittsburgh, Pennsylvania. She strives to provide coverage tailored to meet the client's needs and make it a positive experience. In her free time, you will find her out enjoying Paradise at the beach or enjoying the local bands at the Tiki Bars with
Dana joined our team in 2014, she brings many years of Insurance experience with her from Pittsburgh, Pennsylvania. She strives to provide coverage tailored to meet the client's needs and make it a positive experience. In her free time, you will find her out enjoying Paradise at the beach or enjoying the local bands at the Tiki Bars with her husband of 40 years and counting! She’s always willing to share recent photos of her children and 4 grandchildren and of course we won’t leave out her dog, Duce and her cat Dolly.
Bryan Domian
Alissa Edwards
Dana Gesmond
Bryan is a Financial Professional, with over 20 years of experience, who empowers individuals and families by teaching them how money works. His mission is to help clients protect what they’ve built, grow their wealth with intention, and create lasting legacies through smart financial strategies.
With a client-first approach, Bryan provi
Bryan is a Financial Professional, with over 20 years of experience, who empowers individuals and families by teaching them how money works. His mission is to help clients protect what they’ve built, grow their wealth with intention, and create lasting legacies through smart financial strategies.
With a client-first approach, Bryan provides guidance on everything from insurance and investment planning to retirement and generational wealth transfer. Bryan believes financial literacy is the foundation of financial freedom — and he is passionate about making it accessible and actionable for everyone he works with.
Alissa Edwards
Alissa Edwards
Alissa Edwards
Alissa moved to Englewood from Nashua New Hampshire in 2002, and graduated from Lemon Bay High school in 2005. Although she does miss the change of seasons in New England, she considers Englewood to be her home.
Alissa can be found spending time with her husband PJ, and sons Riley and Jaxon. Her boys are her pride and joy, and she spends
Alissa moved to Englewood from Nashua New Hampshire in 2002, and graduated from Lemon Bay High school in 2005. Although she does miss the change of seasons in New England, she considers Englewood to be her home.
Alissa can be found spending time with her husband PJ, and sons Riley and Jaxon. Her boys are her pride and joy, and she spends every moment she can with them.
Alissa joined Rowley Insurance in 2019 as a receptionist and has worked her way up to become an account manager for our personal lines team.
Dana Smith
Myranda Villacis
Alissa Edwards
Dana joined our team in 2023. She is a seasoned personal lines insurance professional with over 18 years of experience. She has helped many people protect their valuable assets through all the complexity and daily challenges that the insurance industry brings with homeowners, auto, umbrellas, condos, and recreational vehicles. She is
Dana joined our team in 2023. She is a seasoned personal lines insurance professional with over 18 years of experience. She has helped many people protect their valuable assets through all the complexity and daily challenges that the insurance industry brings with homeowners, auto, umbrellas, condos, and recreational vehicles. She is very attentive to the clients needs, and will tailor a policy to fit the coverage needed and provide ongoing support to ensure client satisfaction and security.
Susan Garraus
Myranda Villacis
Myranda Villacis
Susan obtained her 4-40 customer service license and joined Rowley Insurance earlier this year as an account manager. Prior to joining the team she had a 25+ year career in the Title Insurance Industry locally. She is enjoying her new position and looks forward to growing her knowledge within the agency where she can to continue to a
Susan obtained her 4-40 customer service license and joined Rowley Insurance earlier this year as an account manager. Prior to joining the team she had a 25+ year career in the Title Insurance Industry locally. She is enjoying her new position and looks forward to growing her knowledge within the agency where she can to continue to assist clients utilizing her customer service skills, attention to detail, and knowledge of the area
Myranda Villacis
Myranda Villacis
Myranda Villacis
Myranda comes from many years of customer service. Coming out of retail she decided to pursue a career in insurance in 2022. With no prior experience with insurance she started off as a receptionist. This team has offered her many avenues to expand her knowledge and is actively learning something new every day. She has now moved into a
Myranda comes from many years of customer service. Coming out of retail she decided to pursue a career in insurance in 2022. With no prior experience with insurance she started off as a receptionist. This team has offered her many avenues to expand her knowledge and is actively learning something new every day. She has now moved into a roll of processing in the agency. She actively enjoys assisting clients in every need that they have .She looks forward to advancing her career in insurance.
Damon Johnson
Cynthia Cazares
Cynthia Cazares
Damon is a hometown resident here in Englewood and a proud graduate of Lemon Bay High School. With multiple years of experience in customer service, he decided to put that experience to use and begin his career in insurance. His goal is to help a many people as possible in making sure they are protected properly. In his spare time he enjo
Damon is a hometown resident here in Englewood and a proud graduate of Lemon Bay High School. With multiple years of experience in customer service, he decided to put that experience to use and begin his career in insurance. His goal is to help a many people as possible in making sure they are protected properly. In his spare time he enjoys spending time with family and friends, and racing sprint cars. Damon looks forward to learning and expanding his knowledge in the insurance industry.
Cynthia Cazares
Cynthia Cazares
Cynthia Cazares
Cynthia has spent the last 8 years dedicated to the insurance industry helping secure and protect what matters most. She moved to Florida 3 years ago where she has gained a new wealth of knowledge that benefits her clients. Away from the office, her favorite role is being a mother and grandparent making lasting memories with her family.
Blake Lipstein
Cynthia Cazares
Blake Lipstein
Blake was born and raised in the Englewood Area, where he attended all our local schools from Elementary Middle and is a proud graduate of Lemon Bay High School. He then attended the University of South Florida achieving his bachelor’s in marketing in 2015. He came back to Englewood to work in his family’s real estate company and joined t
Blake was born and raised in the Englewood Area, where he attended all our local schools from Elementary Middle and is a proud graduate of Lemon Bay High School. He then attended the University of South Florida achieving his bachelor’s in marketing in 2015. He came back to Englewood to work in his family’s real estate company and joined the Lemon Bay Sunset Rotary. Club. Blake changed careers and joined team Rowley as a commercial sales agent in August of this year and is looking forward to serving the business community and making new connections. He is married to an amazing wife (Alyssa) and they have 2 beautiful daughters and they enjoy Disney trips, and shopping for their daughters.
Carla Bogner
Jason McCulley
Blake Lipstein
Carla moved to Englewood from Cleveland Ohio in 2021 and is an avid Cleveland sports fan, especially the Browns!! After many years in the property management industry, she decided a change was in order and joined Team Rowley Insurance. She is a fully licensed 440 customer service representative and is our front desk coordinator/receptionist.
Jason McCulley
Jason McCulley
Jason McCulley
Jason moved to Florida from Cincinnati, OH in June 2020. He has over 20 years experience in finance and sales. Outside of work, he enjoys spending time with his wife, family, and three dogs. In his free time, he enjoys a round of golf, playing poker with friends and going to beach. He looks forward to becoming an integral part of the pers
Jason moved to Florida from Cincinnati, OH in June 2020. He has over 20 years experience in finance and sales. Outside of work, he enjoys spending time with his wife, family, and three dogs. In his free time, he enjoys a round of golf, playing poker with friends and going to beach. He looks forward to becoming an integral part of the personal insurance sales team at Rowley Insurance.