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Postsecondary Success Manager

Job in Boston, Suffolk County, Massachusetts, 02298, USA
Listing for: CrossroadsMA
Full Time, Seasonal/Temporary position
Listed on 2026-03-03
Job specializations:
  • Education / Teaching
    Youth Development, Education Administration, Summer Seasonal
Salary/Wage Range or Industry Benchmark: 65 USD Hourly USD 65.00 HOUR
Job Description & How to Apply Below

Position Title:

Postsecondary Success Manager
Department/Division: C5 Leaders Program Team
FLSA:
Exempt

Reports to:

Director of Crossroads C5 Leaders
Supervises:
Seasonal Staff Team & Full-Time PSI Coordinator(s)

Location:

Boston & Duxbury
Salary: $65,

About Crossroads and C5 Leaders

Founded in 1936, Crossroads serves over 1,000 children and teens from communities across Greater Boston and Brockton. Our mission is to empower young people to realize their potential and positively impact the world. Crossroads’ programs provide access to opportunities for experiential learning, social-emotional skill development, and relationship building with peers and role models. Our residential settings, intentional mentorship, and powerful culture offer a brave space for participants in Grades 2-12 to test themselves and new ideas as they engage in learning experiences that are rigorous, relevant, and stimulate the development of essential skills.

The primary objective of the C5 Leaders program (Grades 8-12) is to build the capacity of teens to attain a college degree or professional certification. Participants learn skills that empower them to be character-driven, community-focused, challenge-ready, college/career-bound, and committed to a better future (the 5C’s). Over the course of five years, teens refine and practice their leadership skills as they immerse themselves in experiential learning contexts, civic engagement, and college and career exploration.

The depth of peer‑to‑peer and teen‑to‑staff relationships fostered over the course of five years and the intensity of our challenge‑based, experiential learning model are key differentiators between C5 and other youth development programs.

The Crossroads Postsecondary Success Manager is focused on designing and implementing programming and systems to support C5 Leader participants and alumni. The Postsecondary Success Manager will support young people as they explore, select, and succeed in their chosen college or career pathway. The Postsecondary Success Manager will oversee the planning and enactment of college and career exploration experiences, both during the summer months and the school year, with an emphasis on personalized guidance to prepare young people for the transition from high school to college/the workplace.

The manager will supervise the Postsecondary Success Coordinator(s), tasked with coaching participants and alumni through regular check‑ins, support, and feedback.

Each C5 Leader will develop an individualized action plan to guide their progress through the process of exploring, applying to, and selecting the postsecondary option that is the best fit for their needs and aspirations. The PSI Manager will also direct development and execution of a strategy to support C5 Leader graduates in the first two years of their chosen college/career pathway.

The ideal candidate for this position has a background in college access/success advising as well as staff management. This individual must possess strategic planning skills, as well as outstanding written and verbal communication skills. S/he must have a demonstrated interest in serving low‑income and first‑generation college‑bound students and be dedicated to supporting young people to and through college/early career professional certification.

Key

Accountabilities
  • Lead the planning, coordination, and implementation of safe, engaging, and intentional residential summer programming for teens in Grades 11-12 (Road to College Tours and ACT Now Summit)
  • Manage year‑round Postsecondary Success Coordinator(s) to achieve program outcomes
  • Lead the planning, coordination, and implementation of the Apprentice and Summer Corps training programs for leaders in Grades 10-11 who are interested in becoming summer camp counselors.
  • Lead and deliver outstanding experiential leadership curriculum to all teens enrolled in the C5 program during the school year (Grades 8-12).
  • Lead and refine the C5 Leaders college and career exploration, application, and selection efforts, including the facilitation of workshops, college visits, career panels, job shadows, financial aid advising, academic coaching, and family engagement.
  • Facilit…
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