Matt Fenner
COO/CFO - Venture Capital
Matt Fenner has spent decades working alongside businesses during periods that require clear financial direction and consistent operational follow-through. His career, which spans more than 30 years, has focused on acquiring companies, improving their internal structure, supporting growth, and exiting when the opportunity is right. His approach is steady and practical, shaped by direct involvement in the details that influence long-term results.
Fenner developed his early professional base through formal education in accounting and finance. He earned an MBA in Finance and a BBA in Accounting from the University of North Florida. His time in a CPA firm environment provided a strong understanding of financial reporting and discipline. As he transitioned into private business, he applied that foundation in situations where decisions had an immediate financial impact. This experience reinforced the importance of combining financial insight with an understanding of how a business operates.
Matt continued to grow by working in roles that required both analysis and execution. He focused on identifying operational gaps and addressing them with structured improvements. His work often involved strengthening processes, improving financial controls, and aligning operational activities with financial goals. Over time, he developed a consistent approach to tackling challenges across different industries and company sizes.
Fenner played a role in the development and eventual sale of a large, privately owned alarm security company in the United States. His responsibilities included financial oversight and operational support as the company expanded. Following this, he joined Republic Industries as part of its M&A team, contributing to acquisition efforts within a company generating $10 billion in annual revenue. This experience provided insight into large-scale transactions and reinforced the value of disciplined execution.
Matt later served as CFO and startup equity partner for Indian Motorcycles Florida, LLC. In that role, he managed financial operations across 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 andgeneratedg $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 core operations.
Matt later co-founded Caplin Family Offices, operating as Caplin Ventures, where he continues to serve as COO/CFO. The firm has grown into a platform with 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.
Fenner has completed five micro-cap company builds and exits by consistently improving financial performance, scaling operations, and exiting at appropriate valuations. One example includes the sale of Certified Security to Vector Security at a multiple of 4.5x annual recurring revenue.
Matt Fenner continues to work with organizations by focusing on clear financial practices and steady operational improvement, helping businesses move forward with stability and a long-term perspective.
Linkedin: https://www.linkedin.com/in/matt-fenner
