Executive Director

ABOUT Y2Y

Y2Y Network envisions a world where every young person has a safe place to grow and never has to sleep outside.

Y2Y Network’s mission is to disrupt the cycle of homelessness by and for a generation of young adults. Its groundbreaking college partnership model mobilizes young people to provide a safe and affirming environment for young adults experiencing homelessness. Founded in 2015, Y2Y Harvard Square is the nation’s first homeless shelter for young adults. It is run by college students and is affiliated with Harvard University’s Phillips Brooks House Association (PBHA). Y2Y Network has a pilot site in New Haven, CT in partnership with Youth Continuum. In addition to supporting these sites, the organization is transitioning to a focus on building a national movement to break the cycle of youth homelessness.

Y2Y’s peer-to-peer model relies on hundreds of young adults' talents, passion, and leadership. Y2Y meets guests’ needs with a comprehensive program to provide emotional and physical stability and facilitate access to critical resources. Beyond providing shelter, Y2Y’s extensive partner network includes professional healthcare providers, skilled volunteers, and community partners. Student case managers work with guests to access critical resources, including job training, mentoring, mental health care, and permanent housing.

The values of Dignity, Safety, Adaptability, Collaboration, Affirmation and Cultural Responsiveness, Young Adult Leadership Development, and Social Justice drive Y2Y’s work.

THE POSITION

As we prepare for our next growth stage, including developing a Y2Y Network Fellowship Program, we seek an Executive Director with a unique blend of skills and qualities. The ideal candidate is deeply committed to youth-led social change, demonstrates exceptional leadership capabilities, and can craft and execute a compelling strategic vision. We're looking for someone who embraces a collaborative, strengths-based approach and is passionate about positioning young people as leaders in this critical work.

The Executive Director will strategically champion Y2Y Network's youth-driven model and mission to end youth homelessness. Successful candidates will demonstrate an unwavering belief in the power of youth leadership and a deep understanding of how peer-to-peer service models create transformative change. Experience with positive youth development and serving vulnerable populations in a direct service capacity is strongly preferred.

Success in this role requires the ability to authentically engage with and support passionate young adults while fostering their growth as leaders. You'll play a crucial role in amplifying youth voices, developing our overall growth strategy, and building and nurturing a high-performing team that centers youth leadership. We need someone who can anticipate challenges, solve problems proactively, and position the organization for sustainable growth.

As Executive Director, you'll take on comprehensive strategic and operational leadership responsibilities. You'll work closely with our Board of Directors, manage Y2Y staff, and cultivate relationships with various stakeholders, including funders, universities, government agencies, and community partners. Your role will focus on developing and implementing the expansion plan for our new Y2Y Network Fellows program while ensuring the continued success of our current sites. Your overarching mission will be to chart a programmatic and operational growth course that amplifies youth leadership while aligning with our values and objectives.

This position calls for a dynamic leader who can drive Y2Y's expansion while staying true to our core mission of empowering young people to address youth homelessness. Your commitment to youth leadership, strategic acumen, and ability to inspire and mobilize others will be instrumental in taking Y2Y to the next level of impact and reach.

This role reports to Y2Y's Board of Directors and collaborates closely with staff, guests, student staff, and community and university partners. The Executive Director will manage a staff team of four, including the New Haven Student and Community Manager, the Director of Administration, and the Director of Development. The Executive Director will co-manage the Harvard Square Student and Community Manager with the Deputy Director of PBHA. Y2Y's FY25 annual budget is $1MM.

MAJOR FUNCTIONS & RESPONSIBILITIES

As the Executive Director, you will be responsible for the following threads of work:

Organizational Leadership

• Ensure the success and sustainability of current sites and enhance current programs to broaden and deepen the organization’s impact in breaking the cycle of youth homelessness by improving and expanding Pathways offerings
• Build a thoughtful expansion plan for new sites that aligns with Y2Y’s core principles and positions young adults experiencing homelessness, student staff, and volunteers as leaders in the movement to interrupt the cycle of youth homelessness and create a sustainable framework for their leadership to thrive
• Evaluate and strengthen Y2Y Network impact and efficacy by fostering relationships with partners, collaborators, volunteers, staff, donors, governmental agencies, community organizations and program participants

Program Stewardship

• Work closely with the staff, Board, and key stakeholders to design and align programmatic outcomes with strategic goals
• Support and foster a culture that embraces teamwork, mutual respect, transparency, seamless communication, and meaningful mentorship among staff and guests
• Promote the ongoing success of core services by using data to drive decisions and foster a spirit of continuous improvement
• Assess, enhance, redesign (if necessary), and maintain Y2Y Network’s systems and infrastructure, including team management

Team Leadership and Management

• Oversee Y2Y’s efforts to center diversity, equity, inclusion, and the voices of students and youth experiencing homelessness in all decision-making, organizational practices, and culture.
• Nurture a transparent and compassionate culture through high support and high accountability for ambitious outcomes, where staff can bring their whole selves to work and productively and openly engage in critical conversations.
• Develop a staffing structure as the organization scales and hire for new positions as needed.

Fundraising and Partnership Development

• Cultivate, steward, and develop new and existing relationships with community partners and funders to reach organizational growth and sustainability goals.
• Develop, maintain, and support a strong Board of Directors; seek and build Board engagement with strategic direction for effective operations, impactful programming, resource development, and community partnerships.
• Create an ambitious, achievable annual development plan that implements fundraising strategies to secure financial support from various sources, including foundations, corporations, and individual donors and manage the Director of Development to execute that plan
• Cultivate and steward critical relationships such as college and university partnerships, site locations, and federal, state, city, and community-based agencies to reach organizational scale and achieve sustainability

Advocacy and External Affairs

• Strategize with the leadership team on approaches to building important and sustained cross-sector partnerships that can find service and policy solutions that have a demonstrable impact on ending youth homelessness
• Maintain a working knowledge of significant developments, best practices, and trends in the fields of youth homelessness, youth leadership, and university partnerships and build the public profile of Y2Y Network as a sought-after resource in these areas

QUALIFICATIONS & EXPERIENCE

There are innumerable ways to learn, grow, and excel professionally. We respect this when we review applications and take a broad look at the experience of each applicant. We want to get to know you and the unique strengths you will bring to the work. This said, we are most likely to be interested in your candidacy if you can demonstrate the majority of the qualifications and experiences listed below:

• Trajectory of increased breadth and depth of development and management experience gained in high-growth organizations
• Ability to build sustainable and productive partnerships with nonprofits, businesses, academic institutions, and federal, state, and city government agencies
• Demonstrated commitment to, expertise with, and/or passion for working with youth and young adults with deep respect and understanding of the power of youth leadership and peer-to-peer service models
• Comfortable and capable of speaking to all constituents and stakeholders about the power and potential of Y2Y Network’s model
• Ability to compel others to action as a key storyteller of our path to impact, priorities for growth and ongoing contributions to the communities and young people we serve
• Desire to play a key role in achieving an ambitious vision requiring cultural responsiveness, bold thinking, and comfort with pivots to harness opportunity to advance our work strategically
• A proven track record and passion for nonprofit fundraising that is demonstrated in a commitment to maintaining current funders, a zest for cultivating new donors, an ability to generate new revenue streams, and a history of successfully taking organizations to the next level of sustained philanthropic support
• Self-motivated and inspirational problem solver with demonstrated ability to coach, manage, and develop high-performing, diverse teams to achieve strategic objectives
• Intellectual depth, maturity, and the ability to collaborate effectively with colleagues, Board Members, external partners, and direct reports
• Strong analytical skills and proficiency with the use of data to drive fundraising and programmatic decisions
• Service mindset that shows a commitment to working “shoulder to shoulder” to support Y2Y Network’s daily operations and program implementation
• Experience with advocacy, public policy, and systems reform efforts
• Demonstrated commitment to positive youth development and serving vulnerable populations in a direct service capacity is strongly preferred.
• A background in campus and/or community organizing is a plus
• Comfort and experience with working in an entrepreneurial and fast-paced environment that requires nimbleness and the ability to change course while bringing all stakeholders along effectively

LOCATION, COMPENSATION & BENEFITS

This is a full-time, hybrid, remote position. Candidates should live in the Greater Boston Area. The Executive Director will be expected to regularly work from the Y2Y shelter in Cambridge, MA and to visit our pilot site in New Haven, CT as needed with regularity. Additionally, the ED will be expected to regularly meet in person with stakeholders and donors in the Boston Area and to travel as needed to potential expansion sites.

The salary range for this role for this position is $100,00-$120,000 annually. Y2Y offers a comprehensive benefits package including medical, dental, vision & disability insurance, retirement plan, and flexible paid time off. You can find an overview of the benefits here.

HOW TO APPLY

Interested candidates are encouraged to promptly submit their application through our online portal. All applicants will receive a response to their application. Please email rcostello@positivelypartners.org with questions or for support submitting your application.

Candidates who advance should expect:

• initial interviews with the recruitment team at Positively Partners, beginning in November or December 2024
• a virtual interview with members of a Search Committee comprised of Y2Y stakeholders
• A multipart interview and facility tour with Y2Y staff, students, and stakeholders in January 2025

The target start date is Winter 2025. Positively Partners is committed to conducting an equitable, accessible assessment process. If you would like to request an accommodation during the interview process, please email search@positivelypartners.org. Accommodation requests will be handled confidentially.

Y2Y is an equal-opportunity employer and is committed to building a diverse and inclusive workforce. We encourage applications from individuals of all backgrounds, experiences, and perspectives.

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