Site Leader: Family Engagement Specialist SY '26-27

*Role commences August 2026

SITE LEADER- Family Engagement Specialist 

Location: Boston, MA 
Classification: Full-Time, Non-Exempt 
Reports To: Director of ACE Academy 

ABOUT TENACITY 

Since 1999, Tenacity has empowered more than 45,000 Massachusetts youth to graduate from high school and achieve post-secondary success through academic enrichment, racket sports, fitness, and life skills development. We provide year-round programs in Boston, Worcester, and Chelsea that build literacy, critical thinking, and healthy habits while fostering supportive relationships between students and staff. 

Tenacity students consistently exceed local graduation and college completion rates—95% graduate from high school, and 75% pursue or complete post-secondary education, compared to 79% and 38% citywide, respectively. Recognized as a leader in in-school, after-school, and summer learning, Tenacity equips young people with the academic, social, and physical foundation to thrive both on and off the court. 

JOB SUMMARY  

The ACE Academy Site Leader-Family Engagement Specialist leads the successful recruitment, engagement, and retention of middle school students participating in Tenacity’s after-school and summer programs.  This role plays a key part in delivering high-quality academic, literacy, fitness, and family engagement programming designed to foster students’ personal, social, and academic growth.

The Site Leader-Family Engagement Specialist will be entrepreneurial, collaborative, and possess a commitment to further developing their understanding of how to best support students and families in our communities. This person will be “willing to go the extra mile”, have a strong desire to lead, take full responsibility for a site, and be committed to helping Boston’s youth succeed academically and athletically while imparting life skills and promoting character development in preparation for post-secondary success. They will be excited to build and maintain a supportive community for our students that encompasses families, teachers, school leaders, and community partners. 

This role requires flexibility, teamwork, and a passion for youth development, as responsibilities may include occasional evening and weekend events, summer programming, and collaboration with school-day teachers and family engagement teams. 

KEY RESPONSIBILITIES  

Site Management 

• Supervise ACE staff and volunteers at the assigned site to ensure effective program implementation and student support.  

• Conduct mid-year and end-of-year performance evaluations for site staff.  

• Lead and facilitate staff meetings to support communication, collaboration, and program effectiveness.  

• Develop and maintain positive working relationships with school administration, faculty, and community partners. 

Recruitment & Enrollment 

• Recruitment and enrollment of middle school-aged students for the Ace Academy.  

• Ensure accuracy in the maintenance of student enrollment and engagement records in the Tenacity data management system. 

Student Engagement & Program Support 

• Support a high rate of student retention and site attendance through the offering of consistent and engaging programming.  

• Lead planning and facilitation of Tenacity activities at the assigned site, including ceremonies, field trips, and other activities, which will involve some evenings and/or weekends. 

• Based on the assigned site, serve as a bus chaperone for student transportation from a programming site. 

• Lead site behavior management structures and individualized student support. 

• Engage students in all aspects of Tenacity Ace programming. 

Academic Programming & Enrichment  

• Support academic programming by leading small groups of students in collaboration with the Academic Coordinator 

• As needed, meet with middle school teachers to support the Academic Coordinator in better understanding the work students do in their other classes. 

• As needed, provide push-in to classrooms during the school day that have high concentrations of Tenacity students. 

• Meet with teachers of classes that do Tenacity push-ins to identify how best to support Tenacity students in those classes. 

• During the summer, assist with the Summer Tennis and Reading Program. 

• Support rackets programming by leading station activities. 

Family Engagement  

• Reach out to families to share updates about students, including positive phone calls and letting parents know when their student breaks the rules. 

• Schedule and lead family visits in the fall and in the spring. 

• Support caregiver/family participation in Tenacity and school activities, including open houses, parent/teacher conferences, events, performances, etc.   

• Support the families of 8th graders in the high school selection process and connect families with the College and Career Prep team working with Tenacity’s high school students.   

SKILLS AND QUALIFICATIONS  

• 3+ years of experience implementing youth tennis programming, preferably in large group settings 

• Passion for working with kids as a Sports Based Youth Development practitioner and coordinator 

• Previous experience working with urban, multi-cultural constituents 

• Previous experience as a coach or mentor 

• Behavior management experience 

• Strong interpersonal, team development, management, organizational and communications skills 

• Proficiency in verbal and written communication, Microsoft Word, Excel 

• Bilingual with Spanish a plus 

• Drivers License,  a plus 

• Owning a car is a significant plus 

COMPENSATION & BENEFITS 

Salary Range: $60,000-68,000 annually (based on experience) 
Tenacity offers a comprehensive benefits package including health, dental, vision, 401(k) plan, paid time off, and professional development opportunities. 

EQUAL OPPORTUNITY STATEMENT 

Tenacity is an equal opportunity employer. We celebrate diversity and are committed to creating an inclusive environment for all employees. We strongly encourage candidates from all backgrounds to apply.