Operating background
Jeremiah spent 13 years on the executive team at Property Management Inc. (PMI), where he helped grow the company from $22 million to $120 million in systemwide revenue and expand the network from under 100 locations to 450.
He climbed nearly every rung of that growth — Director of Conversions, VP of Operations, Chief Operations Officer, and ultimately Chief Growth Officer — working frontline operations well before executive strategy and board-level reporting. As COO and CGO he was the executive sponsor for marketing, operations, franchise business coaching, acquisitions, partnerships, and development across 450 owner-operators.
That experience spans start-up franchisors through mature brands generating tens of millions in systemwide revenue — across commercial services, property management, and home services. The range matters: the problems of a young system granting its first territories and those of an established brand whose unit count has flattened are different problems, and he has worked both.
He continues to hold a minority equity interest in PMI, acquired through the company's stock option plan during that tenure.
How that shapes Cundiff Capital
At PMI he was also the executive sponsor of the team that built the company's proprietary operating system, adapted from EOS after implementing it across the 20 largest offices in the network. Building the management infrastructure that a distributed business actually runs on is the specific work Cundiff Capital does inside the companies it acquires.
Working directly with franchise systems, franchisee networks, and the operational infrastructure that supports distributed owner-operators informs how he evaluates businesses, assesses management teams, and identifies where a focused growth plan can create meaningful value.