Summer Programming Jobs in Pennsylvania (NOW HIRING)

Director of Summer & Adventure Programming

DREAM Program, Inc.
Department: Programs
Status: Full-Time (35-45 hours/week), Exempt
Location: Philadelphia, PA
Travel: Approximately 85-90%; Must be able to travel to all summer programming sites and potentially to adventure destinations. Participation and leadership at regular multi-day retreats and trainings are required. Overnight travel to support national programming, orientations, and adventure experiences will occur periodically.

Position Summary

DREAM is seeking a collaborative, strategic, youth-centered Director of Summer & Adventure Programming to lead and strengthen transformative summer and adventure experiences throughout the Philadelphia region while helping shape DREAM’s broader vision for summer and experiential learning across the organization.

Based in Philadelphia, this role serves as the regional leader for DREAM’s summer and adventure programming, ensuring that youth living in Philadelphia’s affordable housing communities have access to engaging, high-quality experiences that foster belonging, confidence, literacy, leadership, and healthy development. From neighborhood-based summer day camps to overnight camp experiences, regional excursions, and national adventure opportunities, this position is responsible for creating meaningful experiences that inspire young people to explore new possibilities, build lasting relationships, and discover their potential.

The Director of Summer & Adventure Programming provides leadership for all aspects of Philadelphia's summer programming, partnering closely with youth, families, AmeriCorps members, volunteers, community organizations, and housing partners. This role oversees program quality, staff development, operational planning, family engagement, adventure logistics, and continuous improvement to ensure every aspect of the summer experience reflects DREAM’s commitment to excellence.

This position serves as a key organizational though partner in advancing DREAM’s national summer and adventure strategy. Working collaboratively with regional leaders, the Camp DREAM team, and national staff, the Director helps strengthen systems, develop best practices, expand adventure opportunities, and build scalable program models that enhance summer programming across DREAm’s network. By leveraging successes and innovations developed in Philadelphia, this role plays an instrumental part in shaping consistent, high-quality summer and adventure experiences for youth across the organization.

The ideal candidate is an energetic, relationship-driven leader who thrives in dynamic environments and believes that transformative experiences happen both inside and outside the classroom. They are equally comfortable with coaching staff, building community partnerships, managing complex logistics, leading youth experiences, and thinking strategically about organizational growth. This individual is an adaptable problem-solver who inspires others, embraces innovation, and is passionate about creating life-changing opportunities that empower young people to learn, explore, lead, and thrive.

Overview of Responsibilities

Lead Regional Summer & Adventure Programming

• Provide strategic leadership and oversight for DREAM’s Summer Enrichment and Adventure programs throughout the Philadelphia region, ensuring safe, engaging, and high-quality experiences for youth.
• Champion a culture of belonging, literacy, youth development, and continuous improvement across all summer programming.
• Monitor program quality through site visits, data, and stakeholder feedback, using insights to strengthen program outcomes and youth experiences.

Develop and Support Exceptional Teams

• Recruit, supervise, coach, and develop a high-performing team of summer managers, AmeriCorps members, and seasonal staff.
• Lead summer onboarding, orientation, and ongoing professional learning that equips staff to deliver exceptional programming.
• Foster a collaborative, accountable, and mission-driven team culture grounded in coaching and continuous growth.

Lead Adventure Experiences

• Oversee the planning, coordination, and implementation of regional and national adventure opportunities, including partnerships with Camp DREAM and other experiential learning initiatives.
• Expand access to transformative adventure experiences that encourage exploration, confidence, leadership, and belonging for Philadelphia youth.
• Ensure all adventure programming reflects DREAM’s commitment to youth safety, risk management, and high-quality experiential learning.

Strengthen Regional Operations and Community Partnerships

• Oversee regional program operations, including enrollment, transportation, staffing, budgeting, scheduling, and resource management.
• Cultivate strong partnerships with affordable housing communities, families, community organizations, and other stakeholders to strengthen youth participation and community impact.
• Ensure operational excellence through effective planning, communication, compliance, and responsive problem-solving.
• Partner with regional and national leaders to strengthen DREAM’s summer and adventure programming through shared systems, best practices, and collaborative planning.
• Contribute to national trainings, retreats, special projects, and organizational initiatives that support consistent, high-quality programming across regions.
• Collaborate with regional leaders to strengthen year-round recruitment, hiring, onboarding, and workforce planning for seasonal programming.
• Help develop tools, resources, and systems that build organizational capacity and support successful summer implementation across DREAM.
• Identify opportunities for innovation and continuous improvement that enhance program quality, staff development, and youth outcomes.

Preferred Qualifications and Experience

• Bachelor's degree or equivalent experience preferred.
• 3+ years of experience managing employees, AmeriCorps members, volunteers, or youth development programs.
• Experience supervising teams and implementing strategic initiatives.
• Demonstrated skills in communication, facilitation, and relationship building.
• Experience coordinating large events, retreats, camps, or adventure-based programming preferred.
• Experience working across multiple teams or locations preferred.
• Familiarity with AmeriCorps requirements and mentoring program standards preferred.
• Strong organizational and project management skills.
• Ability to manage competing priorities while maintaining attention to detail.
• Creativity, flexibility, and an entrepreneurial spirit.
• A contagious energy for DREAM's mission and youth development.
• Comfortable working outdoors in all seasons.

Compensation and Benefits

Salary: $55,000-$65,000 annually (*commensurate with experience)

In addition, employees receive:

• Access to Employee Assistance Program.
• DREAM gear/uniform provided and required.
• Reimbursement for work-related travel expenses.
• Opportunities for leadership development and cross-regional collaboration.

Work Environment

This position operates in multiple environments, including indoor offices, remote workspaces, outdoor settings, and community-based locations. The Director of Summer & Adventure Programming will frequently travel throughout Philadelphia and periodically travel to other DREAM regions to support organizational initiatives.

The role regularly interacts with youth, families, volunteers, AmeriCorps members, and staff and utilizes a variety of software systems for communication, program management, and accountability.

Physical Demands

This position requires comfort working outdoors regardless of weather conditions. Duties frequently involve standing, walking, bending, and active participation in youth programming and adventure experiences.

Employees may occasionally lift and move items weighing up to 50 pounds.

About DREAM

DREAM partners with youth and families living in affordable housing communities to close the Opportunity Gap through mentoring, social-emotional learning, and enrichment programs.

DREAM is a flexible, mission-driven workplace that values autonomy and trust. We are looking for someone who takes ownership of their work and thrives in an environment where initiative is recognized and rewarded. This is a role for someone who is energized by meaningful work, comfortable navigating a growing organization, and ready to make a real impact.

Operating across multiple regions, DREAM values collaboration, adaptability, and accountability. We seek teammates who are excited to contribute beyond their immediate responsibilities, support colleagues across the organization, and help strengthen programs for the youth and communities we serve.

Equal Employment Opportunity Statement

The DREAM Program is an equal opportunity employer and incorporated 501(c)(3) organization. DREAM prohibits discrimination and harassment of any kind and provides equal employment opportunities to all employees and applicants.

At-Will Employment

Employment with The DREAM Program is voluntary and at-will. Employment may be terminated by either the employee or The DREAM Program, with or without cause or notice, at any time.