The DREAM Program, Inc.

Associate Youth Service Director

The DREAM Program, Inc.

full-time

Posted on:

Location Type: Hybrid

Location: South Burlington • Vermont • United States

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Salary

💰 $59,059 per year

Job Level

Lead

About the role

  • 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.
Applicant Tracking System Keywords

Tip: use these terms in your resume and cover letter to boost ATS matches.

Hard Skills & Tools
program developmentcurriculum designdata quality managementfundraising strategysupervisionmentoringstrategic planningteam leadershiptime managementrelationship building
Soft Skills
communicationfacilitationcreativityenergyentrepreneurial spiritproblem-solvingcollaborationsupporting social-emotional developmentinclusivityadaptability