Gary Stropoli

Experience: Bearing Harbor Business Advisory, Munich Health North America, AIG, Munich Re American

Roles: CFO, VP Corporate Planning, VP International Finance and Administration

Education: MBA Finance – Regis University
BBA Finance – Hofstra University

Gary Stropoli is an accomplished Chief Financial Executive, business operations leader, and Board member with a proven track record of driving organizational transformations and delivering sustainable growth across multiple industries, including insurance, healthcare, and services. With decades of experience spanning startups, Fortune 100 companies, and international markets, Gary specializes in leading financial turnarounds, implementing cutting-edge technologies, and fostering operational excellence.

Having held key leadership roles, including Chief Financial Officer and Board Member, Gary brings a wealth of expertise in governance, risk management, and compliance. Extensive experience includes serving on audit, risk, and investment committees, establishing Board protocols, and managing complex financial and operational audits. As a recognized expert in the full insurance vertical, Gary has deep knowledge of financial regulation, international banking, and tax, making him a sought-after leader for organizations seeking to navigate the complexities of global markets.

Throughout his career, Gary has built a reputation as a dynamic change agent capable of revitalizing underperforming organizations. He has consistently delivered measurable results by reducing operating expenses, restructuring operations, and integrating innovative technologies to streamline business processes. From startup environments to large global organizations, Gary’s strategic leadership has been instrumental in positioning companies for long-term success.

Notable accomplishments include transforming Best Doctors Insurance from a failing company to a sustainably profitable entity and serving as CFO at Munich Health North America, where he successfully managed financial operations and risk management functions across the North American region. Additionally, Gary played a pivotal role in revitalizing AIG’s Global Reinsurance Division, overseeing reinsurance collateral and optimizing IT capabilities to support effective data analysis.

In addition to his executive leadership roles, Gary is a valued consultant and advisor through his firm, Bearing Harbor, LLC. Through this venture, he partners with small and medium enterprises (SMEs) to apply big business fundamentals that drive profitability and operational efficiency. His guidance has helped numerous businesses achieve strategic and operational goals, leveraging his expertise in financial planning, mergers and acquisitions, and turnaround management.

Gary’s international experience, spanning regulatory frameworks and business operations across multiple regions, positions him as a trusted advisor for organizations looking to expand globally or improve their financial and operational strategies.