Greg Rolland

Greg Rolland, CPA and MBA, currently serves as the Controller at Deerfield Academy, where he plays a pivotal role in overseeing the institution’s financial integrity and operational excellence. In this capacity, Greg leads a dedicated team of accounting and finance professionals, ensuring the accurate and timely reporting of the Academy’s financial position, compliance with regulatory standards, and adherence to internal controls. His expertise in financial analysis and strategic management enables Deerfield to maintain transparency and accountability, vital for sustaining donor confidence and institutional growth within the non-profit education sector.

At Deerfield, Greg is instrumental in managing complex financial processes, including the preparation of comprehensive financial statements, overseeing annual audits, and ensuring the proper management of pension plans. His deep understanding of non-profit financial management allows him to implement best practices in budgeting, internal controls, and tax compliance, aligning financial strategies with the Academy’s mission-driven objectives. Greg’s background in enterprise growth and operational management, combined with his non-traditional path—ranging from directing outdoor leadership programs in Alaska and Montana to Fortune 500 finance roles—brings a unique perspective to his leadership.

His expertise extends to optimizing financial workflows, leveraging tools like Microsoft Excel for detailed financial analysis, and developing strategies that support sustainable growth. Greg’s focus on program management and internal controls ensures that Deerfield’s financial operations are both efficient and resilient, enabling the Academy to navigate the complexities of the education industry while maintaining fiscal responsibility. His comprehensive skill set and industry-specific knowledge make him a key asset in driving the financial health and strategic direction of Deerfield Academy.