Kevin Gear
Director
Kevin Gear
Director
Suite 500
Tampa FL 33607
About
Growing up, Kevin’s father was a Naval officer, so his family moved around the world quite a bit. He has lived in Orlando, San Diego, Okinawa, San Francisco, Guantanamo, and Bethesda. At a young age he learned to adapt to changing environments and how to make new friends and establish new social circles. His family eventually settled in Fort Myers, Florida, where his father started a family business. In school, he was active in track and field, cross country, and soccer, which taught him to compete and navigate the challenges of life, business, and relationships.
At Benchmark International, Kevin represents private business owners in the sale of their companies and helps them to understand their options while achieving their unique exit strategies. His desire to help people achieve their goals is rooted in understanding his clients’ needs and objectives.
Passion
The decision to sell a business can be emotional and overwhelming for business owners, and Kevin enjoys offering his experience to help them navigate the inevitable hurdles, achieve their desired outcomes, and see what is possible.
Education
DePaul University - Accounting & Finance
University of South Florida - MBA, Finance, Marketing
Experience
Kevin Gear is a seasoned business and finance executive with more than 25 years of experience guiding middle-market companies through mergers and acquisitions, capital formation, and strategic growth. Throughout his career, he has served in senior leadership roles where he not only directed complex transaction processes but also built and led high-performing teams. His work has consistently centered on helping business owners and executives navigate pivotal moments whether preparing for a sale, raising growth capital, or restructuring operations to unlock value.
Kevin’s approach blends analytical rigor with practical execution. He has advised on both buy-side and sell-side transactions, managed due diligence from initial engagement to final close, and worked closely with clients to develop long-term financial strategies. Known for his ability to connect the numbers to the broader business vision, he’s also served as an interim CFO, providing hands-on leadership during critical transition periods.
His experience spans a wide range of industries and includes international dealmaking and cross-border team coordination. Kevin takes pride in building trusted relationships with clients, colleagues, and strategic partners, and brings a thoughtful, collaborative style to every engagement. His professional journey reflects a deep commitment to driving results while maintaining integrity, adaptability, and a focus on the people behind the business.