Cheryl C Perez
Job Description
POSITION SUMMARY
The Executive DirectorofSay Yes Cleveland is the organization's top executive, responsible for advancing its mission, providing visionary leadership, and executing strategy across all school-based programs, operations, public and private partnerships, and organizational fundraising efforts. Reporting to the Board of Directors, the Executive Director serves as the primary representative of Say Yes Cleveland to the community, funders, stakeholders, and the public. The role requires a dynamic and strategic leader who can build organizational infrastructure, foster strong partnerships, secure and manage public funding, and lead with a deep commitment to equity and student success.
Full-time, Exempt Reports to:
Board of Directors Location:
Cleveland, OH
ORGANIZATIONAL OVERVIEW
In 2019, our community launched an unprecedented effort to bring the national Say Yes to Education model to Cleveland. The mission of Say Yes Cleveland is to help Cleveland Metropolitan School District (CMSD) students overcome the significant challenges of multi-generational poverty so they can successfully pursue and complete post-secondary credentials. This work is carried out by two separate but complementary entities:
Say Yes Cleveland , an independent nonprofit organization that convenes, mobilizes, and aligns community resources to provide comprehensive, school-based support services from PreK through high school to address social and non-academic barriers that impede post-secondary pursuits; and The
Say Yes Cleveland Scholarship Board,
which oversees and manages the scholarship fund that provides tuition scholarships to every eligible CMSD high school graduate to attend a four- or two-year institution or accredited training program and maintains relationships with higher education partners.
This position-Executive Director of
Say Yes Cleveland -will lead the organization as it evolves its governance structure, fundraising capacity, and long-term strategy for impact.
ESSENTIAL DUTIES AND RESPONSIBILITIES
The Executive Director of Say Yes Cleveland will manage an ambitious cross-sector model. This includes supervising 75+ staff (primarily Family Support Specialists) embedded in schools as well as closely collaborating with the CMSD, City of Cleveland, Cuyahoga County, nonprofit organizations, and philanthropic partners to align and bring resources and support to students. The Executive Director also works in close partnership with the Say Yes Cleveland Scholarship Board, which ensures Say Yes scholarship recipients have the post-secondary campus supports they need to successfully complete their education. Essential duties and responsibilities include:
Provide strategic leadership and oversight for all Say Yes Cleveland school-based programs and operations, aligning efforts with the Cleveland Metropolitan School District and other partners and stakeholders to support the organization's long-term mission, impact, and sustainability. Serve as the organization's chief liaison with public sector funding partners to ensure ongoing sustainability for the Family Support Specialist program and core administrative functions; cultivate relationships with private funders, philanthropic organizations, and corporate partners to support organizational priorities. Serve as the administrative head of the organization, overseeing all daily operations, effective program implementation, organizational workflows, and staff management in student and family services, information technology and data, communications, and development; champion a culture of excellence in execution, strong team cohesion, equity, collaboration, professional development, and staff engagement at all levels. Develop and manage the organization's annual budget (approximately $8 million in 2025-26) in partnership with the fiscal agent, College Now Greater Cleveland, ensuring compliance and effective allocation of resources. Establish and monitor annual organizational goals, ensuring performance metrics and benchmarks are met, and aligning internal progress with Say Yes Cleveland's mission and public commitments. Develop and implement systems, tools, and evaluation frameworks to measure organizational impact, track key performance metrics, and inform data-driven decision-making across student and family support services and leveraging these insights to drive continuous improvement and demonstrate outcomes to funders, partners, and the community. Support and evolve the Board of Directors' governance, including onboarding and engaging new members, defining roles and expectations, and strengthening the organization's long-term leadership pipeline; oversee the creation and successful execution of an organizational strategic plan under the guidance and support of the Board of Directors. Schedule, plan, and facilitate regular board and committee meetings, preparing key updates and materials to support decision-making and transparency. Serve as a voting member of the Say Yes Cleveland Scholarship Board, helping shape policies governing post-secondary tuition scholarships and ensuring alignment with broader educational goals
Requirements
QUALIFICATIONS AND EDUCATIONAL REQUIREMENTS
To perform this role successfully, the individual must demonstrate excellence across strategic leadership, program execution, resource management, governance, operations, stakeholder engagement, and fundraising. The requirements below reflect the knowledge, experience, and character traits necessary for this position:
Master's degree or higher in a related field (education, nonprofit administration/management, law, public policy, business, etc.). While an advanced degree is typical for leaders in similar roles, Say Yes Cleveland also welcomes applications from nontraditional candidates whose career and life experience align with the goals of this role. Minimum of 10 years of progressive leadership experience in the nonprofit, education, or government sectors, including experience leading teams and managing budgets. Proven track record of working with or reporting to a Board of Directors and leading organizational strategy. Experience with county, state, and federal public funding streams and private fundraising. Deep understanding of the Cleveland community, education ecosystem, nonprofit landscape, and cross-sector collaboration. Prior experience with strategic planning and change management, especially during organizational growth, transition, or restructuring phases.
REQUIRED SKILLS AND COMPETENCIES
Strategic thinker with the ability to develop and implement vision-driven, mission-aligned plans. Skilled communicator (written and verbal) with a talent for storytelling, persuasion, and building trust across diverse constituencies. Culturally competent and equity-minded leader who fosters inclusion and belonging. Proficiency in budget management, operational oversight, and data-driven decision-making. Confident public speaker and relationship builder who can represent the organization externally. Deeply collaborative leadership style with the ability to engage and empower a diverse internal team and external partners. Comfort navigating ambiguity, complexity, and the demands of cross-sector partnerships.
PHYSICAL AND TRAVEL REQUIREMENTS
Some early morning and evening commitments will be expected for board meetings, public engagements, and community events. Occasional local, state, and national travel may be required for conferences, stakeholder engagement, and donor/funder relations. Prolonged periods of sitting at a desk and working on a computer are required. Prolonged periods of walking and standing may also occur during school visits or public events. Must be able to lift up to 20 pounds at times for transporting materials or event support
Benefits
WORKWEEK, COMPENSATION AND BENEFITS
This position is based in Cleveland, Ohio, and requires regular in-person presence at the Say Yes Cleveland office, school partner sites, and local partner meetings. Standard Monday through Friday business hours with flexibility for evening/weekend commitments, as necessary.
Salary is competitive and commensurate with experience, with a salary range beginning at $180,000. Say Yes Cleveland offers a comprehensive benefits package, including medical, dental, and vision coverage; generous paid time off; and support for professional development.
The Executive DirectorofSay Yes Cleveland is the organization's top executive, responsible for advancing its mission, providing visionary leadership, and executing strategy across all school-based programs, operations, public and private partnerships, and organizational fundraising efforts. Reporting to the Board of Directors, the Executive Director serves as the primary representative of Say Yes Cleveland to the community, funders, stakeholders, and the public. The role requires a dynamic and strategic leader who can build organizational infrastructure, foster strong partnerships, secure and manage public funding, and lead with a deep commitment to equity and student success.
Full-time, Exempt Reports to:
Board of Directors Location:
Cleveland, OH
ORGANIZATIONAL OVERVIEW
In 2019, our community launched an unprecedented effort to bring the national Say Yes to Education model to Cleveland. The mission of Say Yes Cleveland is to help Cleveland Metropolitan School District (CMSD) students overcome the significant challenges of multi-generational poverty so they can successfully pursue and complete post-secondary credentials. This work is carried out by two separate but complementary entities:
Say Yes Cleveland , an independent nonprofit organization that convenes, mobilizes, and aligns community resources to provide comprehensive, school-based support services from PreK through high school to address social and non-academic barriers that impede post-secondary pursuits; and The
Say Yes Cleveland Scholarship Board,
which oversees and manages the scholarship fund that provides tuition scholarships to every eligible CMSD high school graduate to attend a four- or two-year institution or accredited training program and maintains relationships with higher education partners.
This position-Executive Director of
Say Yes Cleveland -will lead the organization as it evolves its governance structure, fundraising capacity, and long-term strategy for impact.
ESSENTIAL DUTIES AND RESPONSIBILITIES
The Executive Director of Say Yes Cleveland will manage an ambitious cross-sector model. This includes supervising 75+ staff (primarily Family Support Specialists) embedded in schools as well as closely collaborating with the CMSD, City of Cleveland, Cuyahoga County, nonprofit organizations, and philanthropic partners to align and bring resources and support to students. The Executive Director also works in close partnership with the Say Yes Cleveland Scholarship Board, which ensures Say Yes scholarship recipients have the post-secondary campus supports they need to successfully complete their education. Essential duties and responsibilities include:
Provide strategic leadership and oversight for all Say Yes Cleveland school-based programs and operations, aligning efforts with the Cleveland Metropolitan School District and other partners and stakeholders to support the organization's long-term mission, impact, and sustainability. Serve as the organization's chief liaison with public sector funding partners to ensure ongoing sustainability for the Family Support Specialist program and core administrative functions; cultivate relationships with private funders, philanthropic organizations, and corporate partners to support organizational priorities. Serve as the administrative head of the organization, overseeing all daily operations, effective program implementation, organizational workflows, and staff management in student and family services, information technology and data, communications, and development; champion a culture of excellence in execution, strong team cohesion, equity, collaboration, professional development, and staff engagement at all levels. Develop and manage the organization's annual budget (approximately $8 million in 2025-26) in partnership with the fiscal agent, College Now Greater Cleveland, ensuring compliance and effective allocation of resources. Establish and monitor annual organizational goals, ensuring performance metrics and benchmarks are met, and aligning internal progress with Say Yes Cleveland's mission and public commitments. Develop and implement systems, tools, and evaluation frameworks to measure organizational impact, track key performance metrics, and inform data-driven decision-making across student and family support services and leveraging these insights to drive continuous improvement and demonstrate outcomes to funders, partners, and the community. Support and evolve the Board of Directors' governance, including onboarding and engaging new members, defining roles and expectations, and strengthening the organization's long-term leadership pipeline; oversee the creation and successful execution of an organizational strategic plan under the guidance and support of the Board of Directors. Schedule, plan, and facilitate regular board and committee meetings, preparing key updates and materials to support decision-making and transparency. Serve as a voting member of the Say Yes Cleveland Scholarship Board, helping shape policies governing post-secondary tuition scholarships and ensuring alignment with broader educational goals
Requirements
QUALIFICATIONS AND EDUCATIONAL REQUIREMENTS
To perform this role successfully, the individual must demonstrate excellence across strategic leadership, program execution, resource management, governance, operations, stakeholder engagement, and fundraising. The requirements below reflect the knowledge, experience, and character traits necessary for this position:
Master's degree or higher in a related field (education, nonprofit administration/management, law, public policy, business, etc.). While an advanced degree is typical for leaders in similar roles, Say Yes Cleveland also welcomes applications from nontraditional candidates whose career and life experience align with the goals of this role. Minimum of 10 years of progressive leadership experience in the nonprofit, education, or government sectors, including experience leading teams and managing budgets. Proven track record of working with or reporting to a Board of Directors and leading organizational strategy. Experience with county, state, and federal public funding streams and private fundraising. Deep understanding of the Cleveland community, education ecosystem, nonprofit landscape, and cross-sector collaboration. Prior experience with strategic planning and change management, especially during organizational growth, transition, or restructuring phases.
REQUIRED SKILLS AND COMPETENCIES
Strategic thinker with the ability to develop and implement vision-driven, mission-aligned plans. Skilled communicator (written and verbal) with a talent for storytelling, persuasion, and building trust across diverse constituencies. Culturally competent and equity-minded leader who fosters inclusion and belonging. Proficiency in budget management, operational oversight, and data-driven decision-making. Confident public speaker and relationship builder who can represent the organization externally. Deeply collaborative leadership style with the ability to engage and empower a diverse internal team and external partners. Comfort navigating ambiguity, complexity, and the demands of cross-sector partnerships.
PHYSICAL AND TRAVEL REQUIREMENTS
Some early morning and evening commitments will be expected for board meetings, public engagements, and community events. Occasional local, state, and national travel may be required for conferences, stakeholder engagement, and donor/funder relations. Prolonged periods of sitting at a desk and working on a computer are required. Prolonged periods of walking and standing may also occur during school visits or public events. Must be able to lift up to 20 pounds at times for transporting materials or event support
Benefits
WORKWEEK, COMPENSATION AND BENEFITS
This position is based in Cleveland, Ohio, and requires regular in-person presence at the Say Yes Cleveland office, school partner sites, and local partner meetings. Standard Monday through Friday business hours with flexibility for evening/weekend commitments, as necessary.
Salary is competitive and commensurate with experience, with a salary range beginning at $180,000. Say Yes Cleveland offers a comprehensive benefits package, including medical, dental, and vision coverage; generous paid time off; and support for professional development.