High School Mentor

At Summer Search, we believe in 'No Ceilings' and envision a world in which young people, regardless of circumstances, can chart their own destiny. We partner with young people from underserved communities—disproportionately BIPOC and first-generation—during their transition from adolescence into adulthood by connecting them to expansive opportunities, professional mentoring, and a community of support. Summer Searchers recognize their potential and build a toolkit to navigate and challenge systemic barriers, break new ground for their families and communities, and achieve economic equity and a life of purpose.

About the role

Summer Search Boston is seeking a High School Mentor to manage a caseload of approximately 40 high school students, building long-term relationships and providing regular mentoring through a combination of groups and individual conversations from sophomore year through junior year of high school. This role will join a supportive program team serving over 400+ high school students, practicing Summer Search’s unique mentoring approach, preparing students for two challenging summer experiences, supporting post-secondary readiness and matriculation, and contributing to a team committed to learning, social and racial equity, and student success.

Responsibilities

• Student Mentoring and Program Facilitation (60%)
  • 1:1 Mentoring
    • Mentor a caseload of up to 44 high school participants, building relationships and conducting regular mentoring at school, in our office, or by phone.
    • Utilize a mentoring methodology based on adolescent social-emotional development, cultural relevance, and critical consciousness.
    • Facilitate conversations that allow students to reflect on the impact of identities and social/cultural context on their lives.
    • Hold students accountable to year-round program participation and demonstrate a personal commitment to their engagement.
    • Monitor and promote students’ academic, extracurricular, and post-secondary readiness performance.
    • Communicate with students’ families regarding summer experiences and career opportunities.
  • Group Mentoring
    • Conduct bi-weekly in-person group mentoring sessions for sophomores and juniors.
    • Build multi-year relationships with participants and cultivate connections among students and with Summer Search.
    • Create a safe community where students can engage honestly by ensuring each student has space to be heard and challenged respectfully.
    • Set up physical spaces conducive to session objectives.
    • Recognize and respond to student safety situations, caring for both individuals and the group.
    • Adapt facilitation style based on group needs.
• Community Engagement and Partnership (20%)
  • Support or lead outreach presentations and application workshops for prospective students, including 1:1 follow-up.
  • Establish and nurture relationships with staff at partner high schools.
  • Engage school partners proactively in supporting students and coordinating logistics.
  • Respond promptly and thoughtfully to requests from school partners.
  • Attend key milestone events for participants and their families.
  • Know available resources and personnel at partner high schools and how they intersect with Summer Search.
  • Connect participants to college access, mental health, and career resources.
• Data, Caseload Management, and Learning (15%)
  • Ensure meticulous weekly data collection in our program database (Salesforce) to meet organization-wide metrics and goals.
  • Provide curriculum feedback to inform iterative development.
  • Participate in ongoing observation, coaching, training, and professional development.
  • Engage in program evaluation to assess quality, fidelity, and outcomes, including completing feedback surveys after mentoring sessions.
  • Participate in other assigned projects.
• Engage in Site-Wide and Network Initiatives (5%)
  • Attend and engage in regional Signature Events and participant/family events about 3 times per quarter, typically in the evenings.
  • Support project management of participant-facing events (e.g., orientations, summer celebrations).
  • Provide support to the Summer on Call team for participant-related issues during Summer Experiences.

Requirements

• Experience: At least 2 years of professional experience working with student populations served by Summer Search (e.g., low-income families, students of color, LGBTQIA+, English Language Learners, and diverse religious, cultural, and ethnic backgrounds). Group facilitation experience is strongly desired.
• Depth Mentoring: Ability to create an environment where all people feel safe exploring, discussing, questioning, and reflecting on experiences in one-on-one or group settings.
• Accountability: Hold yourself and others responsible for processes, decisions, actions, and commitments to drive high-quality outcomes. Responsive to stakeholder needs and follow through on commitments.
• Teamwork & Collaboration: Value diverse voices, create space for dialogue, handle interpersonal issues constructively, and inspire commitment and trust to achieve common goals.
• Critical Consciousness: Understand root causes of societal discrimination and injustices, reflect on your own privilege and positional power, and apply critical thinking toward liberatory and inclusive practices.
• Technology Skills: Proficiency in meticulous data tracking and management; experience with Salesforce or similar databases is a plus.
• Language Skills: Proficiency in Spanish or Haitian Creole is a plus.

All Summer Search staff bring a commitment to our mission of unleashing students’ potential through mentoring and transformative experiences, as well as the ability to thrive in an environment valuing excellence, gratitude, well-being, diversity, authenticity, and collaboration.

Schedule

Work hours are Monday–Friday, 10:00 AM–6:00 PM, with occasional weekend and evening special events (e.g., student interviews, orientations, summer prep sessions, community events). Work location is hybrid: 3 days in the Summer Search Boston office (Jamaica Plain) and 2 days remote. You may also be required to be onsite at partner schools for Group Mentoring Program 2 times per month. Access to a car or reliable transportation to travel to the office and schools in the greater Boston area is required.

Pay

This is a non-exempt position with a starting pay rate of $31.14 - $34.83 per hour, equivalent to $60,725–$67,910 annually. Summer Search is committed to transparent, equitable compensation practices. Salaries are benchmarked using current market data, and salary bands demonstrate growth potential within the band. Offers are typically made at the starting place of the salary band.

Benefits

• Medical insurance with up to 90% employer contribution.
• Dental, vision, FSA, life, and disability insurance plans.
• 401(k) with employer match up to $2,000 annually.
• Generous time off: 15 vacation days, 10 sick days, and 18 holidays (including 2 floating holidays, a birthday day-off, 10 company-wide holidays, and a 1-week December closure). Plus, Re-Fresh Fridays—a paid full day off the first Friday of every month.
• Comprehensive Employee Recognition Program (years of service awards, spot awards, and professional development funding).
• A four-week paid sabbatical after five years of continuous employment.
• Individual, local, regional, and national training opportunities.
• Commitment to developing leaders from within the organization.
• Organizational culture supporting staff well-being and holistic self-care/community care.
• Ample opportunities to connect with the students and communities we serve.