Deputy Chief of Out of School Time

Arts For Learning Maryland•Baltimore, MD

17h

About The Position

Arts for Learning Maryland is a mission-driven organization that enriches the lives and education of Maryland youth through educational and culturally diverse arts programs. Professional teaching artists partner with educators, schools, and districts to provide arts learning opportunities to students statewide. Reporting to the Vice President of Education, the Deputy Chief of Out of School Time (OST) provides strategic vision, executive oversight, fiscal governance, and cross-team alignment across Extended School Year (ESY), Summer Arts for Learning Academies (SALA), and Afterschool programming. The position has ultimate decision-making authority for OST programs and leads high-level strategy, district partnerships, and program cohesion, while Program Directors manage day-to-day operations. The Deputy Chief directly supervises the Director of ESY, Director of SALA/Afterschool, Special Education Specialist, and Professional Development Manager. This is an exempt position. The role establishes a unified vision and long-term goals for OST, leads team development and performance management, advances antiracist and culturally responsive practices, and tracks program KPIs. It manages district-level relationships and business development, including revenue opportunities and public funding. The Deputy Chief oversees departmental budgets, financial reporting, contracts, grant and MOU compliance, program evaluation, and continuous quality improvement. The position also participates in site visits, key events, Leadership Academies, and cross-team debriefs. Arts for Learning Maryland offers a starting annual salary of $109,000 and benefits including medical, dental, and vision coverage, retirement contributions, and flexible paid time off. Employees are subject to federal and state background checks.

Requirements

Bachelor’s degree in Education, Arts Administration, Public Administration, Non-Profit Management, or a related field.
5–6 years of progressive leadership experience managing large-scale youth development, OST, or educational programs.
3 years of experience directly supervising full-time managerial staff and building collaborative teams.
Proven ability to monitor and manage for results.
Experience securing public grants, writing proposals, or expanding fee-for-service revenue models in a nonprofit setting.
Proven experience managing multi-million-dollar department budgets, including government restricted grants, reporting, and contract/MOU compliance.
Demonstrated track record building and maintaining district-level relationships, such as with public school systems or state education departments.
Commitment to embedding antiracist, equitable, and culturally responsive practices in leadership, staff development, and student programming.
Ability to foster trust, resolve conflict, and promote shared accountability across departments.
Ability to use evaluation frameworks and KPIs to drive continuous program improvements.
Skill building credibility with external stakeholders, steering difficult conversations, aligning competing priorities, and resolving systemic challenges collaboratively.

Nice To Haves

Master’s degree in Education, Educational Leadership, Non-Profit Management, or Business Administration (MBA).
10 years of progressive leadership experience.
5 years of experience directly supervising full-time managerial staff.
Direct familiarity with Maryland State Department of Education policies, Maryland school district structures, and public funding streams.

Responsibilities

Establish a unified vision, guiding philosophy, and long-term strategic goals for OST programs, aligned across teams, departments, and community programs.
Supervise and support direct reports through regular check-ins and performance management.
Develop a high-trust, accountable, results-focused team and support healthy communication and conflict resolution.
Advance antiracist, equitable, and culturally responsive practices across OST programming, staff onboarding, and leadership development.
Partner with the POPs team on team dynamics, staffing structures, and cross-departmental collaboration.
Establish OST program KPIs, report progress to senior leadership, and collaborate across teams to remove operational barriers.
Maintain alignment with the Special Education Specialist and Program Directors to support unified operational and instructional delivery across sites.
Manage high-level relationships with public schools, regional school districts, and external agencies.
Develop program growth and business development strategies, including fee-for-service, public funding, and grant opportunities.
Identify new revenue-generating partnership opportunities and expand program reach and impact.
Represent Arts for Learning in statewide and district-level OST advisory groups, policy committees, and conferences.
Monitor MSDE policies, local district plans, and youth development research to inform strategy and advocate for OST funding.
Oversee OST department fiscal governance, including annual budget development, resource allocation, mid-year re-projections, and financial reporting.
Promote sustainable financial management, risk management, resource optimization, and internal controls.
Build Program Directors’ financial management capacity; ensure project budgets are monitored, contracts and MOUs are executed, and accounts receivable remain low.
Ensure compliance with district MOUs, grant deliverables, foundation terms, and state guidelines.
Oversee evaluation frameworks and continuous quality improvement with external evaluators and the Data & Systems Manager.
Ensure evaluations demonstrate the impact of OST programs.
Help Program Directors address structural barriers while maintaining program fidelity, quality standards, and budget compliance.
Participate in OST activities, including site visits, key events, Leadership Academies, and cross-team debriefs.