Associate Youth Service Director

Role Overview

• 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.
• Support the expansion of DREAM’s programs by working closely with the Regional Director to launch new and grow existing sites.
• Provide direct leadership and oversight for 3 Village Mentoring Chapters , with the goal to expand.
• 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.
• Lead the restructuring and redevelopment of our afterschool program, including assessment, curriculum design, and creation of sustainable program systems during a planned program pause.
• 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.
• Work in close collaboration with the Program Director to help plan and implement fundraising strategies that support program sustainability and growth.
• Provide regular team and one-on-one support while maintaining strong relationships with program sites through consistent visits and partnership management.

Requirements

• 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.

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,
• expanded health benefits (dental and vision) with employee contribution.