Managing Director of Operations & Strategy (MDOS)

Summary

Hit the Books (“HTB”) aims to provide educational resources to underserved communities through a sports-based development approach, with tutoring and mentorship at its core and mixed martial arts as the ‘hook.’ Based out of our 5,000 sq ft facility located in Harlem, NY, Hit the Books serves as an academic, fitness, and community center
that helps make every goal achievable for its students. To learn more about Hit the Books, please visit www.hitthebooksnyc.org.

HTB provides free afterschool educational programs, mixed martial arts classes, and mentorship to students in Harlem in grades 2-8. HTB exposes our students to educational opportunities that may otherwise pass them by, fostering an environment of educational equality. In addition to enhancing the educational resources available to children, HTB has developed into a community within a community where students view the facility as a safe space and second home.

Position Summary
Hit the Books (HTB) seeks an experienced, disciplined, and strategic Managing Director of Operations & Strategy (MDOS) to oversee day to day operations and refine organizational systems and ensure alignment across all programmatic and operational functions. The MDOS will lead HTB’s Directors and Managers, operationalize organizational priorities, reinforce accountability, and ensure consistent, high
quality experience for students, families, and staff. The MDOS is a senior leader who models operational excellence and accountability. This role requires a seasoned professional who can diagnose root causes, build sustainable systems, coach leaders, and
manage complex workflows with clarity, structure, and calm. The MDOS ensures that HTB’s goals, policies, and standards are executed consistently and effectively every day.

Qualifications

• 7–10 years of professional experience, including 2-5 years in nonprofit or youth serving management with a minimum of 3 years direct supervision experience.
• Proven experience building, implementing, and refining organizational systems with project management tools, dashboards, or performance frameworks.
• Experience overseeing multidepartment operations (program implementation, HR, compliance, facilities, and/or youth development).
• Demonstrated success leading organizational change, cross-functional teams, or crisis response.
• Strong analytical and strategic planning skills with the ability to diagnose and solve complex problems with exceptional communication skills with executive-level writing and presentation abilities.
• Experience in afterschool, youth development, education, academic enrichment, or human services a plus

Duties

Core Responsibilities

A. Organizational Leadership & Strategy (30%)

• Serve as the ED’s strategic partner in annual planning, goal setting, scheduling, budgeting, and organizational execution, and translate these priorities into the systems, timelines, deliverables, and accountability structures required for effective implementation for cross-departmental alignment.
• Maintain a solutions-first culture grounded in data, root cause analysis, strategic planning, and disciplined execution, and prepare executive-level reports, dashboards, and briefings that clearly communicate progress, trends, and organizational needs to the ED, Board of Directors, and all stakeholders.
• Anticipate organizational needs, identify performance gaps, and propose strategic solutions with clear recommendations and implementation

B. Operations Management & Systems Building (30%)

• Maintain and reinforce organizational systems for enrollment, attendance, retention, compliance, family engagement, communication, safety protocols, and overall program operations.
• Lead and institutionalize operating schedules for meetings, decision making, planning, reporting, and cross-departmental alignment to ensure clarity, consistency, and disciplined execution.
• Oversee School Aged Childcare (SACC) compliance, Office of Child and Family Services OCFS/ Department of Health (DOH) requirements, vendor relationships, facility operations, and logistics, and strengthen organizational infrastructure to support scale, replication, and long-term sustainability.

C. People Leadership: Supervision, Coaching & Accountability (25%)

• Directly supervise Directors and Managers with clarity, structure, and consistent expectations aligned with yearly organizational goals, KPIs, and reporting systems that ensure consistent alignment and execution.
• Build leadership capacity in strategic thinking, systems planning, decision making, communication, and follow through; coaching staff to proactively communicate, close loops, seek solutions, and operate without repeated follow-up.
• Manage performance with professionalism and consistency, including evaluations, coaching, and corrective action, while maintaining healthy boundaries, emotional regulation, and a calm, executive presence in moments of conflict or complexity.

D. Program Oversight & Quality Assurance (15%)

• Ensure program quality, safety, developmental alignment, and fidelity to HTB’s mission across daily programming, Saturday sessions, and summer programming.
• Oversee academic assessments (e.g. iReady, Hello Insight) and MMA fitness assessments, and monitor attendance, retention, engagement, and performance trends to identify gaps and implement targeted interventions.
• Ensure systems, staffing, and operational readiness support consistent, uninterrupted programming.