Matt Fenner

Matt Fenner is a finance and operations executive with more than 30 years of experience helping entrepreneurs, operators, and investors build businesses that grow and create lasting value. Based in Jacksonville, Florida, his career has taken him from the early stages of startups to executive leadership within some of the largest enterprises in their industries. Throughout that journey, he has developed a reputation for combining financial discipline with practical, results-oriented operational leadership.

Matt currently serves as COO of Caplin Ventures, a Jacksonville-based investment firm he helped launch in 2019. Today, Caplin's portfolio includes 10 operating companies and more than 20 passive investments across healthcare staffing, technology services, engineering, dentistry, medical research, retail, and professional sports. The businesses within the portfolio collectively employ more than 1,000 people and span a broad range of industries, reflecting the firm's commitment to building diversified, durable enterprises.

Earlier in his career, Matt was a member of the senior leadership team at Scott Alarm, where the team worked to build what became one of the largest privately held alarm security companies in the United States. Following the company's acquisition by Republic Industries, Matt joined Republic as an executive leader on its mergers and acquisitions team. That experience, shaped in large part by working within an organization driven by entrepreneur H. Wayne Huizenga, gave Matt a strong foundation in acquisition strategy and the mechanics of creating value at scale.

He later served as CFO and startup equity partner of Indian Motorcycles Florida, LLC, overseeing a network of retail locations throughout Florida with more than 50 million dollars in combined annual revenue. During a period when the Indian Motorcycle brand was actively reestablishing itself in the marketplace, Matt and his team focused on building a strong retail platform and driving continued growth for the business.

Matt also served as a senior financial executive at Convergys Corporation, which was at the time one of the world's largest business process outsourcing firms. In his role leading financial operations for the Wireline Telecom business unit, he oversaw a division with approximately 17,000 employees and roughly 800 million dollars in annual revenue.

His experience also includes guiding micro-cap businesses through growth and successful exits. As CFO of Certified Security, a Florida-based alarm and fire security company with more than 20,000 residential and commercial customers, Matt helped position the business for its eventual sale to Vector Security. That transaction was recognized for achieving one of the strongest valuation multiples in the security industry at the time.

Matt holds an MBA in Finance and a BBA in Accounting from the University of North Florida. He believes that the most successful businesses share common traits: strong leadership, disciplined financial management, operational focus, and a genuine commitment to creating long-term value for employees, customers, and investors.