Dr. Jennifer Cupid-McCoy
Chief Strategy Officer

Dr. Jennifer Cupid-McCoy serves as the Chief Strategy Officer for The School District of Lee County. She earned her Bachelor of Arts degree in Mass Communications from the University of Pittsburgh, a Master of Education in Elementary Education from Cheyney University of Pennsylvania, an Educational Specialist in Educational Leadership from Nova Southeastern University, and a Doctor of Education in Educational Leadership from the University of Central Florida. In addition to being a public-school educator of 35+ years, she served as an adjunct professor at the University of Central Florida. Dr. Cupid-McCoy began her teaching career with New York City Public Schools, then later in Pennsylvania and Florida. She served as an administrator in both Florida and Nevada.

Purpose

The Strategy Division champions the organization's strategic vision to drive successful organizational transformation. We provide expertise and focus to the strategic advancement of goals, fostering innovation, collaboration and resilience, and strengthen stakeholder engagement.

The Strategy Division consists of three primary areas:

• Strategic Planning and Portfolio Management: provides leadership and guidance in the implementation and evaluation of the district’s strategic goals and initiatives. Leads cross-functional teams to ensure that district resources, policies, and initiatives align with long-term goals and operational efficiency.

• School Transformation and Sustainability: leads district-wide efforts to improve underperforming schools and drive student achievement. Builds the capacity of educators to consistently deliver effective instruction that fosters student ownership, drives achievement, and supports long-term school improvement.

• Risk Management and Internal Compliance: Provides risk prevention and mitigation services. Manages all claims for the District. Assures internal fund compliance with School Board rules and State Statutes.