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Enrollment & Match Support Specialist, Site Based Mentoring

Big Sister Boston is seeking an Enrollment & Match Support Specialist for our Site-Based Mentoring team. The Site-Based program is a one-to-one mentoring program which matches girls, age 7-to-15, with adult women mentors in various sites and schools around Greater Boston and Cambridge. The Enrollment & Match Support Specialist supports those matches who meet in school settings. As a Big Sister staff member, you will contribute to a mentor-rich community in which every girl has access to the individual nurturing, guidance and support she needs to become a confident, competent and caring adult.  

The Enrollment & Match Support Specialist is responsible for conducting assessments for potential volunteer mentors (Big Sisters) and mentees (Little Sisters) and making thoughtful match decisions, with the goal of creating long and strong match relationships while also providing case management support to program participants. The Specialist also conducts introductory match meetings to launch new match relationships. 

Strong candidates can connect with and support adults and children from diverse backgrounds, are constantly curious about understanding the needs of others and creative in identifying solutions, and possess organizational, administrative and detail management that is necessary to ensure compliance to safety and other standards. This is a tremendous opportunity for those who are excited about being on the frontlines of direct service for women and girls and understand the importance of maintaining administrative systems to ensure best practices.  

Big Sister is committed to hiring staff who reflect the diversity of the communities we serve. Multilingual, multicultural and candidates of color are strongly encouraged to apply. If you are interested in working at a well-established, dynamic and supportive organization committed to serving girls, please apply. 


  • Conduct assessments of and make matches between potential volunteer mentors (Big Sisters) and mentees (Little Sisters) according to agency standards and goals  
  • Support a caseload of approximately 60 Site-Based matches (Big and Little Sister mentor/mentee pairings)  
  • Maintain strong relationships with school partners 
  • Conduct regular phone and email check-ins with Big Sisters, Little Sisters, and families, in order to: 
    • Provide on-going support related to match activities, child safety, child development, and match relationship development 
    • Provide comprehensive documentation related to strength of match relationship and support needs for each match participant 
    • Share information about community resources, agency activities, and programs  
  • Facilitate positive closure for matches that are unable to continue meeting as part of the program 
  • Re-engage Big Sisters, Little Sisters and families as appropriate after match closure 
  • Conduct match surveys and annual outcome evaluations with Big and Little Sisters  
  • Attend and lead match activities as assigned, seeking opportunities to make meaningful in-person contacts with matches 
  • Assist with agency special events as needed 


  • Bachelor’s degree with at least one year of experience working with youth in direct service, youth development, social work, or a related area   
  • Excellent project management and organizational skills with ability to consistently meet deadlines  
  • Sensitivity to and experience in working with culturally diverse populations and with youth and women and with the ability to build strong, healthy and productive relationships 
  • Ability to effectively facilitate programming for youth and adolescents 
  • Passion and a proven track record of success in developing and managing productive partner relationships, particularly public schools 
  • Excited about and effective in working autonomously and within a cross-functional team   
  • Facility with Microsoft Office Suite or comparable platforms and comfort with data management systems (Big Sister uses a Salesforce database platform) 
  • Availability and flexibility to work some weekday evenings (scheduled in advance), as well as travel to varying local venues as necessary 
  • Availability and flexibility to travel to various sites within Greater Boston and Cambridge 

Reports to: Director of Site-Based Mentoring 

Language Skills: Written and oral fluency in English; candidates who also have proficiency or fluency in other languages, especially Spanish, Cantonese, or Mandarin, are strongly encouraged to apply 

Start date: October 1, 2022  

Location: Big Sister Association Offices, 20 Park Plaza, Boston, MA. Our office maintains a hybrid working model that allows staff flexibility to work remote and in office. This position also requires travel to and working from the program sites. 

Compensation:This position offers a competitive salary starting at $51,411. Full-time, exempt position. Comprehensive benefits package including paid time off and health benefits. 

Please sendcoverletter and resume withsubjectline Site-Based Mentoring Enrollment & Match Support Specialist to:hr@bigsister.org.Please attach your cover letter and resumé as a Word document or a PDF.   

Big Sister Association of Greater Boston is an equal opportunity employer and does not discriminate on the basis of race, ethnicity, sexual orientation, nationality, ability, age, gender identity or gender expression or any other characteristic protected by federal, state or local laws.