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DEPUTY CHIEF OF OUT OF SCHOOL TIME (OST)

About Us

Arts for Learning Maryland (formerly Young Audiences of Maryland) is devoted to enriching the lives and education of Maryland’s youth through educational and culturally diverse arts programs. Through Arts for Learning, professional teaching artists from all disciplines partner with educators, schools, and school districts to provide -- on average -- over 560,000 hours of learning in, through, and about the arts to more than 155,000 Maryland students annually.

Arts for Learning is a mission-driven organization that values community, innovation, and passion. The staff, board, and teaching artists have a shared commitment to advance equity in the field of education by working tirelessly to generate opportunities for students to imagine, create, and realize their full potential through the arts.

 

Job Description:

Reporting to the Vice President of Education, the Deputy Chief of OST provides strategic vision, executive oversight, fiscal governance, and cross-team alignment across all Out of School Time (OST) initiatives—including Extended School Year (ESY), Summer Arts for Learning Academies (SALA), and Afterschool programming. The Deputy Chief holds ultimate decision-making authority for OST programs, driving high-level strategy, district-level partnerships, and systemic program cohesion while empowering Program Directors to handle day-to-day operational execution.

FLSA Status: Exempt

Reports To: Vice President of Education

Direct Reports: Director, ESY; Director, SALA/Afterschool; Special Education Specialist; Professional Development Manager

 

Responsibilities Include:

Strategic Leadership & Organizational Alignment (35% of time)

• Establish a unified vision, guiding philosophy, and long-term strategic goals for OST at Arts for Learning, ensuring alignment across multiple teams, departments, and community programs.

• Lead and supervise direct reports (Director, ESY; Director, SALA/Afterschool; Special Education Specialist; Professional Development Manager), facilitating regular check-ins and performance management to support team growth, healthy communication, and operational accountability.

• Develop a high functioning team grounded in high trust, accountability, focus on results, and commitment with an ability to move through conflict.

• Embody and advance antiracist, equitable, and culturally responsive practices across all OST programming, staff onboarding, and leadership development.

• Partner with the POPs team to ensure healthy team dynamics, appropriate staffing structures, and collaborative pipelines across departments.

• Establish KPIs for OST Programs and regularly share progress with the senior leadership team, working collaboratively across teams to remove operational roadblocks.

• Maintain regular alignment and touchpoints with the Special Education Specialist and Program Directors to ensure unified operational and instructional delivery across sites.

Partnership & Business Development (25% of time)

• Manage high-level, district-level relationships with Public Schools, regional partner school districts, and external agencies to expand OST learning opportunities and ensure that services provided meet and exceed partner expectations

• Drive business development and program growth strategies, identifying fee-for-service, public funding, and grant opportunities in collaboration with executive leadership.

• Drive program growth in reach and impact and develop new revenue-generating partnership opportunities.

• Represent Arts for Learning in statewide and district-level OST advisory groups, policy committees, and conferences.

• Stay current on Maryland State Department of Education (MSDE) policies, local district board plans, and youth development research to inform organizational strategy and advocate for OST funding.

Fiscal Governance & Contract Administration (20% of time)

• Oversee master fiscal governance for the OST department, leading annual budget development, resource allocation, mid-year projections, and financial reporting in collaboration with finance leadership.

• Ensure department's financial success is sustainable, manage risk, optimize resources and ensure internal controls are in place, 

• Build financial management muscle among Program Directors, ensuring project budgets are monitored, contracts/MOUs are executed, and accounts receivable remain low.

• Ensure department compliance with district MOUs, grant deliverables, foundation terms, and state guidelines.

Program Quality, Evaluation & High-Level Oversight (20% of time)

• Oversee evaluation frameworks and continuous quality improvement strategies in partnership with external evaluators and the Data & Systems Manager to demonstrate programmatic impact.

• Ensure that evaluations demonstrate the transformational impact of A4L’s OST  programs. 

• Support Program Directors in removing high-level structural barriers while maintaining program fidelity, quality standards, and budget compliance.

• Dedicate time across overall duties to direct participation across all OST program aspects, including site visits, key events, Leadership Academies, and cross-team debriefs.

 

Qualifications:

While no one candidate will possess every quality outlined for this position, the successful candidate will fit many of the following professional qualifications and personal attributes:

• Education: Bachelor’s degree in Education, Arts Administration, Public Administration, Non-Profit Management, or a related field.  

• Experience: 5-6 years of progressive leadership experience managing large-scale youth development, out-of-school time (OST), or educational programs.

• Leadership & Management: 3 years of experience directly supervising full-time managerial staff (e.g., Program Directors, Specialists) and building high-functioning, collaborative teams. A proven ability to monitor and manage for results.

• Revenue Generation: Experience securing public grants, writing proposals, or expanding fee-for-service revenue models in a non-profit setting.

• Fiscal Management: Proven experience managing multi-million dollar department budgets, including large government restricted grants and reporting and contract/MOU compliance.

• Strategic Partnerships: Demonstrated track record of navigating, building, and maintaining district-level relationships (e.g., with public school systems or state departments of education).

Preferred Qualifications:

• Advanced Degree: Master’s degree in Education, Educational Leadership, Non-Profit Management, or Business Administration (MBA).

• Experiences: 10 years of progressive leadership experience and 5 years of experience directly supervising full time managerial staff.

• Local System Knowledge: Direct familiarity with Maryland State Department of Education (MSDE) policies and local Maryland school district structures, and public funding streams.

Core Competencies & Other Skills

• Equity & Culturally Responsive Leadership: Deep commitment to embedding anti-racist, equitable, and culturally responsive practices into staff development and student programming as their own leadership practices.

• Conflict Resolution & Team Building: Ability to foster an environment of high trust, healthy conflict resolution, and shared accountability across multi-departmental pipelines.

• Data-Driven Decision Making: Skill in translating evaluation frameworks and KPIs (developed with data managers/external evaluators) into continuous programmatic quality improvements. 

• Partnership Diplomacy: Proven skill in building trust and credibility with external stakeholders, with a strong ability to steer difficult conversations, align competing priorities, and collaboratively resolve systemic challenges.

 

Compensation:

We offer a starting annual salary of $109,000 and an attractive benefits package that includes medical, dental, and vision healthcare coverage, retirement contributions, and a flexible paid time off policy.

 

To Apply:

For consideration, please apply on our website at artsforlearningmd.org. Please do not send applications that include headshots or photos of yourself. No phone calls or recruiters, please. All employees will be subject to a federal and state background check in accordance with state and federal law.

Arts for Learning Maryland is an Equal Opportunity Employer committed to cultivating a diverse workforce and equitable workplace. We encourage applications from individuals of all backgrounds, regardless of race, ethnicity, gender, sexual orientation, gender identity and expression, age, national origin, veteran status, and disability. All qualified applications will be given equal opportunity.