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.

The DREAM Program, Inc.

Open Positions (1)

Management

Associate Youth Service Director