Location: Hartford, CT (local travel required; periodic travel to New Haven and other sites as the model expands)

Type: Full-time
Reports to: Chief Operating Officer

Position Summary
Our Piece of the Pie (OPP) is hiring a Director of Youth Leadership & Development to lead the Hartford Youth Service Corps (HYSC), a paid service-learning program grounded in Positive Youth Development principles and practices that offer youth and young adults ages 16–24 early exposure to workplace expectations through community-based projects. HYSC is youth development first, using service-learning to build belonging, leadership skills, and readiness through meaningful community contribution and supportive relationships. This leader is accountable for daily program operations, staff supervision, partner worksites and agreements, youth engagement, and achievement of program outcomes and grant deliverables. The role also supports planning and readiness for expansion into New Haven and contributes to a strong organizational culture by modeling OPP values and supporting a positive team environment.

Key Responsibilities

• Lead day-to-day program operations, schedules, staffing, and service project execution
• Supervise and develop a team delivering youth engagement, coaching, and group experiences rooted in Positive Youth Development practice
• Build and manage community-based worksite partnerships through Worksite Agreements that support supervision and real learning experiences
• Drive program performance and outcomes including participation, retention, service-hour completion, and successful transitions
• Coordinate wraparound referrals and follow-through with partners for youth needs (education re-engagement, legal, behavioral health, housing resources, parenting supports)
• Engage school officials and education partners to support attendance and re-engagement coordination as applicable
• Maintain municipal and community stakeholder relationships that support service projects and placements
• Ensure documentation, compliance, and reporting practices are strong and aligned with program commitments
• Support funder communication through performance updates and participation in site visits and presentations
• Contribute to expansion readiness activities for New Haven as assigned
• Model OPP values and contribute to a strong, youth-centered organizational culture

• Bachelor’s degree required, master’s preferred
• 5+ years’ experience in youth development, service-learning, workforce, or related youth-serving programs; 2+ years supervisory leadership
• Demonstrated ability to manage program performance, outcomes, and operations
• Experience building partnerships and managing formal agreements (Worksite Agreements, MOUs, or similar)
• Strong communication, problem-solving, and relationship-building skills
• Commitment to youth-centered, equity-driven practice