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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: $65,000-75,000

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.

About Crossroads and C5 Leaders

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.

  • Facilitate Grade 11 and 12 postsecondary planning by providing coaching focused on high school completion, creation of college application checklists, college application support, financial aid form completion and the college/job training enrollment process.

  • Build and maintain partnerships with college admissions offices, career training programs, local businesses, and organizational partners to leverage opportunities for student success.

  • Engage in data collection and analysis to support data-informed practices.

  • Engage families in supporting students through the facilitation of college and career planning, access and affordability workshops.

  • Oversee coaching, check-ins, group sessions, and data collection from program graduates in the first two years of their chosen postsecondary pathway, following high school graduation.

  • Recruit, hire, train, supervise, and inspire a diverse team of seasonal and school year staff to achieve program outcomes. Maintain a high level of applicable professional knowledge and best practices through ongoing professional education and relationships with colleagues and experts in the field.

  • Develop and foster strong relationships with families, teens, and partners to ensure we are maintaining a culture of high expectations and outstanding outcomes. Support the annual recruitment, interviewing, and onboarding of a new class of teen participants.


Areas of Emphasis:

  • Ensure that the highest levels of safety are in place at all times, prioritizing the physical and mental well-being of all participants and staff.

  • Foster and promote a culture of joy, inclusivity, and optimism.

  • Focus on enacting outstanding postsecondary programming that results in all C5 Leaders reaching program outcomes.

  • Collaborate in design and enacting high-quality staff training and ongoing coaching to ensure that standards for professionalism, program improvement, and staff development are met.

  • Demonstrate strong problem-solving skills, and the ability to identify connections and relationships between concepts, resources, and people.

  • Generate innovative solutions to program challenges. Support implementation of measurement and evaluation systems for tracking youth development toward program outcomes.

  • Foster a culture of respect and appreciation for Crossroads, the young people we serve, our staff, the facilities, and the natural environment where our programs are offered.

  • Supervise teams and collaborate with facilities/maintenance staff to ensure a high level of cleanliness and facility readiness; promote a culture of “Leave No Trace.”

  • Collaborate with the development team on donor and grant-based fundraising opportunities and contribute to the culture of philanthropy.


Supervisory Authority:

  • Partner with the C5 team, the Director of Management & Evaluation, the Chief Operating Officer, and the Executive Director to develop and implement annual priorities that ensure program standards and youth development outcomes are advanced.

  • Exercise lead decision-making over all elements of the day-to-day programming operations during College Tour and ACT Now Summit.

  • Supervise and coach summer and school year staff to build their capacity to deliver outstanding experiential programs within the context of a joyful, inclusive community.

  • Develop and manage the summer program budget to balance appropriate investment with efficiency.


Work Environment & Culture:

A successful candidate would embrace the following organizational norms:

  • Proactively contribute to a healthy team and organizational culture Willingness to be a flexible and adaptable teammate

  • Eagerness for intra- and inter-departmental collaboration and clear, thorough communication

  • Respect for others across diverse populations and a commitment to anti-racist practices

  • Engagement in culturally responsive practices and communication with colleagues, families, and teens

  • Ability to travel to communities around Greater Boston and Brockton – a valid driver’s license is required

  • Ability to accommodate occasional non-traditional hours during the school year that may include evenings, weekends, and overnights

  • Ability to engage in overnight programming in a remote, rustic camp setting during the summer months.


Knowledge & Skills:

  • Demonstrated passion for working with youth and a genuine belief in their potential for success

  • Deep familiarity with Boston/Brockton educational landscape

  • Ability to analyze and interpret program performance data and make data-driven adjustments to maximize impact

  • Ability to self-direct and prioritize among competing goals and to initiate process improvements

  • Strong achievement orientation with exceptional time management skills and demonstrated ability to multitask

  • Unquestioning integrity and an unshakable belief in the mission of Crossroads.

  • Commitment to diversity, equity, inclusion, and belonging.

  • Collaborative, engaging leadership style with mature interpersonal skills and the ability to manage multiple, competing priorities and deadlines.

  • Strong work ethic; ability to lead by example and be effective in a fast-paced, high-energy environment.

  • Self-starter who can work independently and take initiative.

  • Keen attention to detail and strong organizational skills

  • Effective team-builder and problem-solver who remains calm under pressure.

  • Polished communication and interpersonal skills with an ability to establish strong relationships via email, phone, and in person with families, campers, agencies, schools, volunteers, and staff.

  • Ability to safely and effectively manage risk.

  • Ability and enthusiasm to work evenings, weekends, and overnights including up to ten weeks during the summer months.

  • Willingness to obtain skills certifications, as appropriate.

  • Positive approach, can-do attitude, sense of humor, and grace under pressure.


Education & Experience:

  • Bachelor’s degree or equivalent work/life experience

  • Demonstrated experience in a role related to post-secondary support or college counseling experience, with at least two in a supervisory role

  • Demonstrated ability to coach, train and supervise a diverse group of staff and to develop a climate of trust, respect, and accountability.

  • Experience with creating and leading high-quality programs to meet desired outcomes.

  • Deep commitment to and experience prioritizing and maintaining the highest levels of child safety.

  • Experience working in a diverse community with first generation students and families

To download a pdf of this job description click here.

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