Associate Youth Service Director

The Dream Program • South Burlington, VT

3d • $59,059

About The Position

We are seeking an Associate Youth Service Director to guide and strengthen our Northern Vermont operations. This is an opportunity for a collaborative leader to work with a team to build upon the region’s strong foundation, bring people together, grow to new sites, and continue to strive for programmatic excellence. The ideal candidate will be skilled in overseeing youth programs and fostering a supportive and cohesive team culture by working alongside staff, volunteers, and community partners to ensure the region thrives. This role is about connection, growth, and laying the groundwork for long-term success, making it a rewarding opportunity for someone passionate about mentorship, community-building, and impact-driven leadership. If you’re a confident leader ready to make a lasting difference, this is your opportunity to drive meaningful change. The DREAM Program is committed to fostering a welcoming and inclusive environment where all staff, volunteers, youth and families have the opportunity to thrive. We believe in continuous learning and growth, and we encourage members to engage with curiosity, openness, and a commitment to making a meaningful impact. Our mission is to close the Opportunity Gap by providing mentorship and enriching experiences that support youth from a wide range of backgrounds. We seek teammates who bring unique and varied perspectives, experiences, and skills. DREAM values individuals who are dedicated to creating an environment where everyone feels seen, supported, and empowered. Overview of Responsibilities of the Associate Youth Service Director: The Associate Director works in close strategic partnership with the Regional Director as part of the region’s core leadership team, sharing responsibility for advancing DREAM’s vision and impact. While the Director provides overall strategic direction and external leadership, the Associate Director serves as a key thought partner and operational leader, helping translate regional priorities into action. Together, they collaborate on planning, decision-making, and problem-solving, ensuring the region’s growth is both strategic and sustainable while fostering a strong, supportive team culture. As a hands-on leader, the Associate Director oversees multiple Village Mentoring Chapters, supports closely with one Guided Mentoring site, supervises and coaches staff and AmeriCorps members, and ensures consistent, high-quality implementation of DREAM’s mentoring model across programs. They lead major initiatives including summer programming, afterschool program redevelopment, staff hiring and onboarding, data quality efforts, and collaborative fundraising work. In close coordination with the Director, the Associate Director provides day-to-day leadership and execution, helping guide regional strategy while supporting staff success, strong partnerships, and lasting impact for youth and families.

Nice To Haves

• 2+ years of experience in managing a group of employees, service members and/or volunteers.
• Demonstrated experience working directly with youth, with the ability to build positive relationships, support social-emotional development, and foster safe, inclusive, and engaging environments for young people.
• Demonstrated practice or education serving and supervising individuals who have a variety of lived experiences in a manner that is respectful and aware of how those experiences impact who they are as individuals and as a community.
• Experience supervising and leading a strategic visioning and execution process.
• Demonstrated skills in communication and facilitation with and among teams.
• Experience supervising and maintaining an organizational property, office, and/or program space.
• Computer proficiency: comfort with Microsoft Office apps, Google's GSuite and email communication; database experience; accounting software experience.
• Familiarity with AmeriCorps grant requirements and mentoring program requirements as expressed by CNCS and state and local regulations, respectively.
• Demonstrated ability to manage time and set priorities while giving consideration to staff, the organization, and the self.
• Creativity, energy, and an entrepreneurial spirit.
• A contagious energy for DREAM’s work.
• Comfortable working in an outdoor environment in all seasons.

Responsibilities

• Expand DREAM’s Reach As the Associate Director, you will support the expansion of DREAM’s programs by working closely with the Regional Director to launch new and grow existing sites. This includes cultivating strong partnerships with community and housing organizations, establishing DREAM as a key volunteer opportunity on local college campuses, and connecting with families in partner housing communities to enroll youth.
• Deliver Excellent Programming You will provide direct leadership and oversight for 3 Village Mentoring Chapters , with the goal to expand. This includes program coordination, mentor and staff support, and consistent implementation of mentoring model and organizational standards. You will supervise and coach chapter leadership to strengthen program delivery, problem-solve challenges, and support positive mentor–mentee relationships. You will collaborate on and co-lead the strategic onboarding of volunteers, AmeriCorps members, DREAM families, and other regional stakeholders. You will work closely with the rest of the NVT leadership team to coordinate trainings, resources, and operational support to ensure chapters are well-equipped and aligned.
• Summer Program Leadership As the Associate Director, you will act as the central coordinator for our Summer Enrichment Programs, including co-designing and co-implementing summer member orientation, ensuring safety and supervision with daily on-site presence, and leading a regional focus on literacy. This also includes being the lead on local summer hiring to ensure that programs are fully equipped and staffed - hiring is done in collaboration with the entire Youth Service team in the region. This includes recruitment, interviewing, selection, and onboarding of summer staff.
• Afterschool Program Development and Restructuring You will lead the restructuring and redevelopment of our afterschool program, including assessment, curriculum design, and creation of sustainable program systems during a planned program pause. You will collaborate with team members in other regions that are running afterschool program to gain their input and design a clear program structure that strengthens quality, consistency, and youth engagement. You will create tools, resources, and systems to support consistent implementation across sites and staff. You will prepare the program for relaunch through staff training plans, documentation, and implementation guidance.
• Data Quality and Management You will support efforts to maintain accurate, up-to-date program data by overseeing our database systems, supporting staff in data entry practices, and ensuring consistent data quality across programs.
• Fundraising Collaboration and Advancement You will work in close collaboration with the Program Director to help plan and implement fundraising strategies that support program sustainability and growth. Assist in planning and executing fundraising events, campaigns, and outreach initiatives. Contribute program insights, data, and stories to strengthen grant applications, reports, and donor communications. Help coordinate internal efforts to ensure fundraising initiatives are aligned with program priorities and timelines.
• Provide Supervision and Leadership You will work closely with a dynamic team, who are doing work to coordinate local programming with mentor volunteers, and support AmeriCorps members. You will provide regular team and one-on-one support while maintaining strong relationships with program sites through consistent visits and partnership management. As part of the All-DREAM Program Leadership team, you will collaborate with leaders across the Northeast in regular virtual meetings. Additionally, alongside the regional director, you will assess and adapt the region’s strategic plan and goals to align with available resources and evolving community needs.

Benefits

• Group Medical Insurance for the employee paid at 100% of cost the plan (no probationary period - plan is based on our current group offering in Vermont - a “bronze” plan level)
• five weeks (25 work days) paid time off (PTO) inclusive of vacation, sick and personal days
• eight (8) paid holidays (including six (6) single days, a winter break from December 24-January 1 and a November break)
• free access to Employee Assistance Program and its corresponding benefits
• free access to Amazon Prime buying and streaming services
• paid membership in position-specific professional organization
• access to professional development opportunities
• DREAM gear/uniforms
• access to 3% employer match retirement plan, and expanded health benefits (dental and vision) with employee contribution

What This Job Offers

• Job Type: Full-time
• Career Level: Director
• Education Level: No Education Listed