Matt Fenner Male • United States of America

Matt Fenner served as CFO and startup equity partner for Indian Motorcycles Florida, LLC. In that position, he oversaw financial operations for multiple retail locations, generating more than $50 million in annual revenue. His work supported the development of a stable retail presence for a recognized brand during a period of renewed activity. His focus remained on maintaining financial consistency while supporting operational needs.

Matt Fenner of Jacksonville also worked at Convergys Corporation, where he co-led financial operations for a business unit that employed 17,000 people and generated $800 million in annual revenue. During that time, he helped improve margins by $22 million, eliminated over $11 million in billing errors, consolidated 30 systems into three, and supported sales efforts that generated more than $50 million in new contract revenue. These efforts were aimed at improving efficiency and strengthening overall business performance.

Fenner later co-founded Caplin Family Offices, operating as Caplin Ventures, where he continues to serve as COO/CFO. The organization has grown to include 12 operating companies and more than 1,000 employees across multiple sectors. Revenue has increased from $30 million in 2018 to a projected $200 million by year-end 2026. He has also led due diligence and structuring for 17 Seed and Series A investments totaling $24 million.

Matt has completed five micro-cap company builds and exits, following a consistent process focused on improving financial performance, scaling operations, and exiting at the right time. One example includes the sale of Certified Security to Vector Security at a multiple of 4.5x annual recurring revenue.

Matt Fenner continues to focus on helping businesses build stronger financial structures and maintain steady operational progress, thereby supporting long-term growth in practical, sustainable ways.