Arena Careers

In the United States, students from underserved communities – disproportionately BIPOC and first-generation – face systemic inequities in school, in the workforce, and in life. Nevertheless, these young people possess unique strengths, resilience, and limitless potential. At Summer Search, we believe in 'No Ceilings' and envision a world in which young people, regardless of circumstances, can chart their own destiny.

Since 1990, Summer Search has partnered with young people 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.

THE OPPORTUNITY

Reporting to the Chief Impact Officer, the Executive Director (ED) will lead the vision, overall strategy, and direction of Summer Search Boston, an established and far-reaching program currently serving 400 high school and 600 post-secondary participants. The ED is responsible for driving fundraising success, ensuring high-quality program delivery, and leading a dynamic team that supports youth in achieving personal and professional success. This role requires a balance of strategic vision, relationship-building acumen, and disciplined execution to strengthen both local outcomes and network-wide priorities.

WHAT YOU’LL DO

Organizational & Strategic Leadership

Provide strategic leadership over Summer Search’s network-wide OKRs to achieve mutually beneficial goals in Boston.

Strategic Leadership and Fundraising

You will lead Summer Search Boston’s overall strategy in close partnership with national leadership, including the Managing Director of Development and other senior leaders, to ensure strong alignment with organizational priorities and long-term growth. You will design and execute a comprehensive annual fundraising plan to meet or exceed Boston’s $3.7MM goal, playing a highly visible role in cultivating, soliciting, and stewarding major donors, foundations, and corporate partners.

You will partner closely with the Boston Board of Directors to expand Summer Search’s visibility and donor base, leveraging their networks and influence to deepen philanthropic support. In collaboration with national and regional colleagues, you will strengthen fundraising systems and strategies that sustain and grow revenue over time.

Financial Management

You will oversee the financial health of the Boston region in partnership with the National Finance Team, leading the development and management of the annual budget. You will monitor expenditures, ensure responsible and sustainable use of resources, and maintain strong alignment between financial decisions and strategic priorities. Through this work, you will uphold a high standard of fiscal transparency, accountability, and long-term sustainability.

Board Relations & Governance

You will work closely with the Boston Board Chair and Board of Directors to ensure effective governance and strategic alignment with Summer Search’s mission. You will engage board members as active partners in fundraising, advocacy, and community-building efforts, while also leading the recruitment, onboarding, and development of new members who reflect the diversity and values of the communities we serve.

Program Excellence

You will partner with the Regional Program Director and National Program Team to ensure the delivery of high-quality, outcomes-driven programming across student recruitment, mentoring, summer experiences, and post-secondary success. You will use data to monitor performance, evaluate impact, and inform continuous improvement, while contributing to organizational storytelling by translating outcomes into compelling narratives.

Team Leadership

You will lead and support a Boston-based team of 18 staff, directly managing the Regional Program Director and supporting the leadership of the Director of Development. You will foster a collaborative, inclusive, and high-performing team culture grounded in clear expectations, strong communication, and shared accountability. As part of a broader organizational team, you will collaborate closely with national departments to ensure alignment, coordination, and operational excellence across all functions.

External Engagement and Advocacy

You will serve as the primary ambassador and spokesperson for Summer Search Boston, representing the organization with funders, partners, and the broader community. You will build and maintain relationships with civic leaders, policymakers, and peer organizations to expand Summer Search’s influence and impact.

You will champion youth mentorship and advocate for the needs and potential of young people, while elevating Summer Search’s work through public speaking, community engagement, and storytelling. In all aspects of your leadership, you will advance the organization’s commitment to equity, diversity, inclusion, and belonging, fostering meaningful dialogue and action both internally and externally.

WHO YOU ARE

You are an experienced strategic leader who combines vision with disciplined execution to drive organizational success. You excel at aligning diverse stakeholders of staff, donors, board members, and partners around shared goals and measurable outcomes. You hold a deep commitment to equity, inclusion, and the belief in young people’s limitless potential.

Specifically, we are seeking candidates who bring:

• EXPERIENCE & SKILLS: At least 10 years of progressive leadership experience in the nonprofit, education, or youth development sectors.
  • Proven success in fundraising, donor relations, board and partnership development.
  • Demonstrated experience managing high-performing teams and cultivating inclusive, result-oriented cultures.
  • Strong financial acumen and ability to manage budgets and operations effectively.
• STRATEGIC ACUMEN: You anticipate, articulate, and prepare for various outcomes and use this skill to collaboratively develop objectives and priorities that are informed by data and align with the organizational direction.
• PEOPLE MANAGEMENT: You coach, guide and support members of your team towards achieving individual and collective goals. As a leader you embody practices to effectively hold space, facilitate professional growth, amplify strengths, and hold staff members accountable. Your management style reflects your ability to be adaptive, responsive, and supportive of your team to show up as their authentic and full self.
• ACCOUNTABILITY: You hold yourself and others responsible for processes, decisions, actions, and commitments to results to drive high quality outcomes. You're responsive to the needs of stakeholders and follow through on commitments.
• CHANGE MINDSET: You have a desire to learn, grow and improve with an evolving organization. You prioritize transparency and communication and recognize that it is critical to supporting others to thrive amidst change.
• TEAMWORK & COLLABORATION: You value many voices, are comfortable creating space for dialogue and handle interpersonal issues constructively. You inspire and foster commitment, connection, enthusiasm and trust and motivate others to achieve common goals.
• TECHNOLOGY SKILLS: Proficient in PowerPoint, Canva and Excel.

In addition, 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 that values excellence, gratitude, well-being, diversity, authenticity, and collaboration.

LOCATION AND TRAVEL

This is a hybrid position with at least 3 days a week of the employee’s choosing in the office in Jamaica Plain and up to two days of remote work weekly. Evening and/or weekend work will be required occasionally as needed for events and donor engagement. Occasional travel to other Summer Search sites and national convenings is required up to four times per year.

COMPENSATION AND BENEFITS

Competitive and transparent salaries. This is an exempt position with a starting salary of $180,000. Summer Search is committed to transparent, equitable compensation practices. Salaries are benchmarked using current market data and salary bands are created to demonstrate the growth, potential within the band. Typically, offers are made at the starting place of the salary band. The Hiring Manager partners with the Talent Team to ensure offers are appropriate, competitive and maintain internal equity.

Well-being, flexibility, and ongoing learning and development are pillars of our culture. We value our staff and are committed to creating an environment where every individual feels seen, heard and valued. Investments in our staff include:

• Medical insurance with up to 90% employer contribution
• Dental, vision, FSA, life and disability insurance plans
• 401 (K) and Employer Match up to $2,000 annually
• Generous time off including 15 vacation days, 10 sick days, and 18 holidays (2 floating holidays of your choice, a birthday day-off, 10 company-wide holidays, and a 1-week December closure).
• Refresh Friday’s – a paid day off the first Friday of every month!
• A 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
• A commitment to developing leaders from within the organization.
• An organizational culture that supports staff well-being and holistic self-care/community care
• Ample opportunities to connect with the students and communities we serve.

OUR COMMITMENT TO EQUITY, DIVERSITY, AND INCLUSION

With a staff that cares deeply about social justice and racial justice, we believe that diverse perspectives and backgrounds create a rich work environment and enhance our ability to pursue our mission. We are committed to building an organization with critical consciousness in order to impact how we work with students, as well as how we work together as a team. We hope you will join us as we continue to build a justice-centered organization that fosters a work environment where people from all backgrounds are welcomed and valued.

TO APPLY

This search is being run by NRG Consulting Group. Please contact Naomi Roth-Gaudette and Arianna Haut with questions at [email protected]. Applications will be reviewed on a rolling basis. The preferred application deadline is 5/1/2026.

SUMMER SEARCH IS AN EQUAL OPPORTUNITY EMPLOYER.