Director of Summer Programming

Job Posting Summary:

Tenacity is looking for a seasoned, dynamic, mission-driven Director of Summer Programming to oversee the planning, coordination, and execution of our Tenacity Summer Tennis, Reading and Pickleball Program at 18 sites across Boston. This leadership position is responsible for supervising seasonal staff, ensuring program quality, managing partnerships, and supporting family engagement through strong leadership and managerial skills. Expertise in tennis or pickleball not required. The Director will serve as the primary point of contact for summer-related matters and report directly to the CEO.

This is a seasonal, full-time position running from mid-May through August 22nd. There is potential for the role to evolve into a year-round position based on performance and organizational fit.

Position Title: Director of Summer Programming

Reports To: Chief Executive Officer (CEO)

Location: Boston, MA

Classification: Full-Time, Seasonal (Start Date ASAP – August 2025)

Compensation: $20,000–$25,000 for the season, based on experience. Includes 403(b) retirement plan and health insurance coverage.

Tenacity’s Mission:

To provide a Pathway to Post-Secondary Success for Boston’s at-risk youth by combining literacy, life skills, family engagement and fitness/tennis to improve their scholastic, character, and physical development.

Since 1999, the Summer Tennis Reading & Pickleball program (STRP), jointly offered through a partnership with Boston’s Parks and Recreation Department and the City of Boston, has provided an enriching learning environment for city youth, keeping minds and bodies active during the summer.

During July and August, this public-private partnership serves nearly 4,200 Boston youth ages 6–15 through programming held in many municipal parks and a few Departments of Conservation and Recreation locations across the city. This dynamic program is offered free of charge on summer weekday mornings and afternoons.

Each age group meets for a session that includes tennis and fitness activities and a variety of light reading activities.

This public-private partnership helps the City of Boston employ around 100 Boston teenagers and young adults as staff in the STRP, providing fun jobs with opportunities to build leadership skills. These positions are coordinated through Boston’s Youth Engagement and Employment program and the Boston Centers for Youth & Families. All STRP site leaders and staff 18 and older are USTA Safe Play certified.

Responsibilities:

• Oversee daily operations of summer program sites, ensuring smooth registration and delivery of high-quality programming
• Manage logistics, supplies, attendance tracking, and coordinate the Mayor’s Cup with City of Boston officials.
• Supervise Sector Leaders and seasonal staff; lead training and onboarding efforts, including June 30–July 2 orientation.
• Partner with HR to finalize hiring, process payroll, address staff issues, and allocate support where needed.
• Act as the main point of contact for external partners and ensure timely submission of required program reports.
• Collaborate with internal teams (HR, Operations, Finance) to support audits, reporting, and data tracking systems.
• Lead communication with families through weekly updates, addressing questions, concerns, and weather alerts.
• Maintain a responsive and professional approach to family engagement throughout the summer season.
• Ensure all sites meet safety standards and staff are trained on emergency protocols and procedures.
• Respond to urgent issues and maintain readiness for any site-level emergencies or incidents.

Skills & Qualifications:

• Strong communicator with excellent organizational, problem-solving, and conflict resolution skills
• Ability to thrive in a fast-paced environment and build positive relationships with diverse stakeholders
• Experience in youth development or program management preferred
• Proficiency with Microsoft Office, Google Workspace, and Active Network a plus
• CPR/First Aid certification (or willingness to obtain) preferred

Experience Requirements:

• 3–5 years of experience in youth development, program management, or education-focused nonprofits
• 2 years of supervisory experience, ideally managing seasonal or part-time staff
• 5–7 years in leadership roles within camps, after-school programs, or similar settings is preferred
• Experience coordinating with city agencies or community partners is preferred
• Background in managing large events or multi-site programming is a plus

Equal Opportunity Statement

We are an equal-opportunity employer and do not discriminate based on race, religion, gender, age, sexuality, gender identification, or physical ability.