Director of Pathway Programs (High School Mentoring)

Big Brothers Big Sisters of Eastern Massachusetts
Boston, MA

At Big Brothers Big Sisters of Eastern Massachusetts (BBBSEM) we believe that every child deserves to have at least one mentor in their corner to ignite and defend their potential. That's why  we are committed to promoting the healthy development of children through the nurturing of continuing, one-to-one friendships with caring responsible adults, supported by trained professional staff . To accomplish this we partner with schools, workplaces, and volunteers all over Eastern Massachusetts to bring our program and services closest to youth who need them.

Role Summary: BBBSEM is seeking an Director of Pathway Programs to oversee the creation and support of mentoring relationships based in 4 local high schools, help the team implement a high-quality program, and maintain and strengthen high school and post-secondary partnerships. You will lead a results-oriented staff already working within schools in Eastern Massachusetts.

Key Responsibilities:

Staff Management and Program Implementation

  • Manage (including hiring and onboarding) a team of program staff at varied levels towards successful program implementation
  • Cultivate a high achievement, results-driven environment that supports the implementation of our model and meets programmatic outcomes. Work with Chief Program Officer to set clear goals and outcomes
  • Ensure staff are effectively executing their roles in-school by conducting site visits (including 1-2 live observations per month per staff), attending live events (often happening during the evening 1-2 times p/week), and forming relationships with key school stakeholders to improve program quality.
  • Be a first option for school day coverage when staff are unavailable
  • Support staff as they provide cohort level and individualized coaching to mentors. Ensure direct reports are up to date in their case management responsibilities including documentation, tracking and follow-up
  • Guide staff to use data to track progress towards their goals, identify necessary interventions to increase success, and identify pairs that need additional coaching or support. Model how to use data for continuous improvement
  • Partner with college counseling services at each high school to streamline the college research, application, and transition process, further embedding and strengthening our program
  • Monitor application and tracking of post-secondary transition steps, including enrollment in the Post-Secondary Program

Strategic Partner and Grade Team Leader

  • Collaborate with other Program leaders to support local trainings, planning meetings and professional development opportunities for staff and constituents to improve program quality and impact
  • Represent Pathways programming in critical agency conversations (Board meetings, leadership retreats, etc.)
  • Help assess risk and ensure safety compliance across Pathways programs. Manage, in coordination with the Chief Program Officer, escalations from staff regarding procedural, clinical, and safety/risk management issues encountered in supporting match relationships
  • Partner with our volunteer recruitment and development teams to identify, vet and pitch new partnerships that will help expand our pathways programming
  • Cultivate relationships with local corporations, organizations and thought leaders to attract resources and content that will expand and strengthen our programming

Basic Qualifications

  • 7+ years of professional experience with at least 3 years working in an educational or youth services environment, and experience in the field of college access or success
  • Prior experience managing professional staff who must use critical thinking, assessment and relational support skills (guiding, supporting, confronting, advising, negotiating) to do their work
  • Willingness and ability to frequently travel to different locations throughout Eastern Massachusetts
  • Highly proficient with MS Office (Outlook, Word, Teams, etc.), Experience with Salesforce, and knowledgeable about business analysis tools and systems

Desired Qualifications

  • Prior non-profit leadership experience, customer relationship management, or human/social services
  • Strong leadership skills with the proven ability to manage, motivate, and develop individual staff and teams to exceed quantitative and qualitative goals
  • Demonstrated comfort and ability to work with and motivate a wide variety of people, including youth and adults, with a preference for candidates with experience in racially, ethnically, and socio-economically diverse urban and/or recent immigrant communities
  • Proven ability to direct multiple projects concurrently. Superior project management, organizational, and problem-solving skills.
  • Experience analyzing data and making strategic decisions based on that data
  • Experience working with diverse populations of adult and youth; experience working with volunteer populations desired. Demonstrated ability to provide superior service and apply sound judgment when working with these groups.
  • Excellent verbal, written and interpersonal communications skills
  • Enthusiasm, creativity, a positive sense of humor, and a “can do” attitude

Salary Range: $83,000 – 91,000 per year

Posted 2026-01-12

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