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Teen Match Support Specialist

Big Sister Boston is seeking dynamic individuals to join Our Big Futures team to support our teenage Little Sisters and their Big Sisters. OBF focuses on supporting Little Sisters from 14 to the age of 24, to achieve sustainable financial independence via career development and/or college success. Our Big Futures team engages the Big Sisters to offer tailored support to their Little Sisters, enhances the 1-1 mentoring experiences of our teens and young adults by providing workshops, leadership training, partnership engagement and enrichment opportunities to prepare them for their future. 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 Teen Match Support Specialist is responsible for providing case management and coaching specifically to teen aged youth to support program participants to ensure longer and stronger relationships between Big Sister and Little Sister. This includes offering guidance and support to teenagers in various aspects of their personal growth, including navigating career paths, college options, and milestones specific to adolescence to aid in their personal development journey. This role also supports the development of the Teen Programming department through workshops, partnership with Our Big Future resources and exciting opportunities that promote the financial independence via career development and/or college success of our youth. As needed, this role also conducts introductory match meetings to launch new match relationships.  

Strong candidates can connect with and support adults and teens 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. Candidates of color, multilingual and multicultural candidates 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. 


Caseload Management & Match Support  

  • Support a caseload of teen Little Sisters and their Big Sisters once they turn 14; Occasionally conduct introductory match meetings for 14 year olds (virtual primarily or at times in Little’s homes)   
  • Maintain an assigned caseload of approximately 60 Community-Based matches   
  • 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, teen safety, teen development, and match relationship development 
    • Provide comprehensive documentation related to strength of match relationship and support needs for each match participant  
    • Share information and coaching around engaging with Our Big Futures events and opportunities, community resources, agency activities, and programs 
  • Provide specific coaching and support to teens in key OBF focus areas such as education and career pathways, wellbeing management, financial literacy, career readiness, leaderships and goal setting  
  • 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 

Administrative and Interdepartmental Support  

  • Support staff training (staff observations and lead process workshop, as assigned) 
  • Update all appropriate databases (Matchforce, Sisterforce) in a timely and accurate manner   
  • Gather and document target Our Big Future programming outcomes and help identify the most effective recruitment strategies 
  • Attend and lead Our Big Futures events and workshops as assigned, seeking opportunities to make meaningful in-person contacts with matches and enhance the engagement with Our Big Futures  
  • Attend special agency events as assigned 


Candidates taking on roles in our 1-1 mentoring program must have a high school diploma/GED equivalent and meet one of the following criteria: 

  • A documented bachelor’s degree or completion within six months in field relevant to direct service, youth development, social work, or other related area 
  • A documented associate degree or two years of higher education experience in related field and two years of relevant work experience in direct service, youth development, social work, or a related area 
  • At least four years of relevant work experience in direct service, youth development, social work, or a related area 

Along with the above criteria, candidates should have some of the following qualifications to be successful in the role. 

  • Passionate about Big Sister’s mission and excited to support and coach program participants in healthy mentoring relationships   
  • Ability to build strong, healthy and productive relationships   
  • Sensitivity to and experience in working with culturally diverse populations and with girls and women 
  • Effective presentation and public speaking skills for audiences of 25-100+  
  • Ability to clearly communicate in writing and speaking to diverse audiences across different sectors (e.g. neighborhood communities, college students, corporate audiences)  
  • Passion and a proven track record of success in providing excellent, supportive direct service  
  • Excellent project management and organizational skills with ability to consistently meet deadlines    
  • Exceptional time management skills and ability to multitask  
  • Demonstrated skill to take initiative, be proactive in problem-solving and - implementing new procedures to improve customer service   
  • Excited about and effective in working autonomously and within a cross-functional team 
  • Enthusiastic about learning with the ability to give and receive constructive feedback   
  • Ability to clearly communicate on the phone and in person as well as via email  
  • Facility with Microsoft Office Suite and comfort with data management systems (Big Sister uses a Salesforce database platform)  
  • Availability and flexibility to work in person on weekday evenings and weekends on a regular basis, as well as travel to various sites within Greater Boston  
  • Experience in a social service setting, youth development, public service, or direct service strongly preferred   

Don’t meet every qualification? Studies have shown that women and people of color are less likely to apply to a job unless they meet 100% of the job qualifications. At Big Sister, we are committed to building a diverse and inclusive workplace environment where staff can grow and develop their passions and skills. If you are passionate about the role and the organization, we encourage you to apply even if your experience does not meet every requirement. You could be just the person we are looking for this role or other opportunities  

Reports to: Manager of  Our Big Futures

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

Start date: September

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 around Greater Boston to youth programming sites

Compensation: This position offers a competitive salary starting at $52,953.Full-time, exempt position. Comprehensive benefits package including paid time off and health benefits.

Please send resumé with subject line Teen Match Support Specialist to: [email protected]. Please attach your resumé as a Word document or a PDF.