Associate Youth Service Director

The Dream Program•South Burlington, VT

4d•Hybrid

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
Deliver Excellent Programming
Summer Program Leadership
Afterschool Program Development and Restructuring
Data Quality and Management
Fundraising Collaboration and Advancement
Provide Supervision and Leadership

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.