Jessica Greenfield

Chief Financial & Administrative Officer at City Year

In this role Jessica oversees the preservation and creation of value in partnership with City Year’s senior leadership team through leadership of the financial, technology, legal and federal grants management for City Year’s annual operating budget and staff of 4,500. In this role, Jessica enables sustainable enterprise growth strategy in new and existing markets, co-leads transformations of the organization operating model to expand the benefits of national support services, and effectively deploys financing vehicles on the cutting edge for tax-exempt organizations, including swaps and derivatives, while maintaining compliance and risk controls. As an officer of the organization, Jessica is also charged with leading City Year’s investment, finance and audit committees.

A Massachusetts native, Jessica joined City Year in 2003 as a Fireman Fellow. While at City Year, Jessica served as City Year's Vice President of Operations Transformation, leading the development of the operating model transformation project processes, practices, and frameworks to increase frontline staff time focus on students, corps, and our stakeholders. Prior to this role, Jessica was City Year’s Vice President of Financial Planning and Analysis, where she oversaw the annual operating and grant budgeting process for the enterprise, developed financial models for organizational and site growth, and designed financial and revenue reporting tools and processes. Prior to that, she served as City Year's National Director of Service, responsible for the standardization of our school-based service model. In her very first role at City Year, Jessica successfully managed the development of 287 Columbus Avenue as our national and City Year Boston headquarters.

Jessica brings to the CFAO role many years of experience in a broad range of disciplines, including finance, operations, governance, strategic planning, and change management. Her responsibilities have included risk management, compliance, marketing and sales, personnel management and training, financial modeling, contract administration, and customer satisfaction at public and private sector organizations including The Community Builders, MassDevelopment Finance Agency, and Public Financial Management Inc.

Jessica has been an active volunteer in her children’s school communities, serving in capacities as varied as Board Chair and room parent. She has also served several terms in leadership of her synagogue's Board of Trustees. She graduated from Yale University with a degree in Urban Studies and the MIT Sloan School of Management MBA program where she was awarded the Seeley Scholarship prize. She is the proud parent of Hannah and Theo.



  • Chief Financial & Administrative Officer

    Current role

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