Crossroads, President & CEO

Crossroads (Edgility Consulting)

Job Description


Since its inception in 1936, Crossroads has stood as a leader in Boston's youth development sector, committed to unlocking the potential of young individuals and challenging the notion that their capabilities are dictated by social and economic circumstances. With 74% of families being low-income, Crossroads ensures financial barriers don't limit access to transformative programs. Each year, Crossroads engages over 1,000 young people in summer and school year programming focused on four areas of development: leadership; civic engagement; social-emotional learning; and postsecondary access and success. Through a decade-long continuum of year-round experiential learning, Crossroads provides opportunities for exploration, growth, and mentorship, playing a crucial role in shaping a brighter future for the youth it serves.

Crossroads’ unique model offers a continuum of programming that engages children from age six through young adulthood. Program offerings include:

  • Overnight Summer Camp Program (Grades 2-8):
    • Creating the space for young people to explore new environments, engage in fun and new experiences, and develop healthy relationships with fellow campers and staff
  •  Junior Leaders Program (Grades 3-7):
    • Providing residential summer camp and school year enrichment experiences that build confidence, strengthen social-emotional skills, promote mentorship, and provide opportunities for play and physical fitness
  • C5 Leaders Program (Grades 8-12): 
    • Year-round experiential learning that includes outdoor education, leadership development, community service, and college and career exploration.
  • Camp Wing Day Camp
    • Fee-based program providing engaging activities in a variety of program areas for youth aged 5 to 16. 

To learn more about Crossroads, please visit


Working closely with the Board of Directors and senior leadership team, the President will serve as the primary external face of the organization, leading all fundraising, partnership development, and brand-building for Crossroads as it continues to build its presence as a leader in the youth development field. This includes thinking creatively about its multiple sites, identifying new revenue streams, strengthening new partnerships and geographies, and extending the organization’s brand.

In addition, the President will oversee all strategy, finance, operations, and staff, directly supervising executive leadership team members in a strongly mission-driven organization. The President will report to the Crossroads Board and will be supervised by the Board Chair and Executive Committee. This is an ideal opportunity for a mission-driven and entrepreneurial leader to partner with and inspire a talented leadership team and committed Board, build upon a strong financial foundation, and lead an already successful organization into its next era of impact.


Organizational Leadership and Management

  • In collaboration with the Executive Leadership Team and Board, review and refine Crossroads' vision and strategic priorities, building consensus and support among key stakeholders

  • Lead the organization through development, implementation, and monitoring of strategic and operational plans which translate the vision into action

Programmatic Excellence  

  • Oversee high-quality, impactful programs that advance the youth development outcomes articulated in the Camper and C5 Outcomes Frameworks

  • Deepen the impact of existing programs and experiences, particularly outdoor and adventure programs

  • Drive a culture of assessment and continuous improvement in programs to ensure impact

Operational Excellence

  • Partner with COO and staff to ensure continued high levels of operational efficiency and effective use of resources while delivering high-quality experiences for young people and families engaged with Crossroads

  • Invest in and maintain sites in a manner that reflects a commitment to providing young people from diverse backgrounds with the very best learning environments and a deep respect for the natural world

People Leadership/Organizational Health

  • Prioritize diversity, equity, inclusion, and belonging as areas of focus for organizational learning, practices, and decisions

  • Promote a healthy workplace environment with shared commitment to one another and organizational priorities

  • Deepen organizational commitment to the growth and development of all staff

  • Strengthen and leverage 30-person board 

Long-Term Financial Sustainability

  • Work closely with the Board and Director of Development to build and execute a robust and diverse annual and long-term fundraising plans to secure needed resources

  • Serve, along with the Director of Development and Director of Leadership Giving, as a primary fundraiser in identifying and cultivating sustainable relationships with major donors, foundations, and corporations

  • Partner with Board/volunteer leadership to solicit funding and non-financial support from individuals, foundations, and other sources of support. 

  • Partner with the Board and Staff  in the management of fundraising strategies, events, and activities, continually building a pipeline of potential new supporters for Crossroads

  • Provide internal and external leadership for donor-centric fundraising events and initiatives to ensure fundraising priorities are successfully incorporated and implemented to meet financial goals

Communications and Partnerships

  • Serve as spokesperson and ambassador for the organization, sharing results, building visibility, creating institutional partnerships, and serving as a thought leader in the youth development field

  • Work with team to develop messages, materials, and vehicles that effectively  and consistently communicate Crossroads’ mission and programs

  • Build strategic and deep partnerships with Boston and Brockton communities and leaders


  • Commitment and connection to Crossroads mission that resonates on a deeply personal level

  • Demonstrated leadership, high energy, enthusiasm, charisma, vision, and deep empathy for all members of the Crossroads community

  • Demonstrated experience in significant leadership roles, accompanied by a track record of outstanding performance and results, ideally in youth development and/or camp settings

  • Ability to build meaningful relationships with youth and communicate the Crossroads story in a manner that is authentic, culturally competent, and compelling to a diverse group of youth, families, staff, and community supporters

  • Experience and expertise in creating and implementing a strategic plan and building the organizational structures, systems, and competencies to effectively deliver on the goals

  • Demonstrated experience building strong and strategic relationships in the non-profit, philanthropic, corporate, and political communities

  • Experience working collaboratively with a Board of Directors, members of a management team, and in managing and leading teams

  • Significant experience engaging key stakeholders as meaningful supporters using proven approaches to fundraising; a successful track record of fundraising

  • Ability to recognize talent and potential, coach and inspire, provide effective feedback, and bring out the very best in a team

  • Business and fiscal management skills including, finance, P&L, budgeting, and forecasting

  • Experience with real estate and facilities management

  • Outstanding interpersonal skills, written and verbal communication skills, with the ability to articulate the Crossroads’ story to prospective and current supporters, partners, and other stakeholders

  • Bachelor’s degree is required, Master’s/advanced degree preferred


This position offers a competitive salary range of $160,000 - $190,000 and robust benefits including medical, dental, and retirement. More details can be provided upon request.


Please submit a resume online at For additional questions about this position or to speak with someone about your interest, please contact Corina Hopson at