Lead Director, Workforce Development

Founded in 2003, Urban Initiatives is a nonprofit organization that uses the power of sport and play to empower Chicago's youth to achieve academic success, develop social-emotional skills, and build social capital.

Today, Urban Initiatives reaches more than 100,000 young people annually across more than 80 Chicago schools and community sites. Through youth development, workforce development, adult learning, and community engagement, we help young people build relationships, develop essential life skills, and connect to meaningful opportunities that prepare them for lifelong success.

Urban Initiatives is dedicated to intentionally fostering a climate of purposeful inclusion in our workplace, and candidates of diverse backgrounds and identities are strongly encouraged to apply. Urban Initiatives is an Equal Opportunity Employer. Personnel are chosen based on ability without regard to race, color, religion, sex, age, national origin, veteran status, disability, marital status, sexual orientation, gender identity, or gender expression, in accordance with federal and state law.

Position Overview

Urban Initiatives is seeking a Lead Director of Workforce Development to launch and grow our youth workforce development strategy. This role leads the launch of UI Coaches Lab, connecting our existing leadership, coaching, employment, and career exploration programs into one coherent pathway for young people ages 14-24. Year one centers on building and launching the program — recruitment, employer engagement, staff supervision, and direct youth experience — while laying the groundwork to integrate initiatives like Coach for Success, Community Member to Coach, Summer Employment, and Pathways to Purpose into a seamless long-term strategy.

This is a hands-on role requiring both strategic vision and direct execution. The ideal candidate will draw on Urban Initiatives' existing curriculum, data, employer partnerships, and program infrastructure to build a cohesive participant experience, and will be just as comfortable facilitating youth workshops and coaching staff as building employer relationships and managing complex projects end to end.

The position will report to the Chief Innovation and Learning Officer.

Our Culture

Our healing-centered approach to youth development helps young people reach their full potential and puts YOU right in the middle of making an impact that will shape generations of Chicago youth.

We are coaches by trade and bring this expertise into our work environment. You can expect ample learning opportunities, growth mindsets, a culture of feedback and transparency, and fun as a core value.

Are you ready to put passion into action to build a stronger Chicago?

What You Would Do:

Lead the Launch of UI Coaches Lab

• Serve as the lead responsible for the launch and implementation of UI Coaches Lab.
• Translate strategic plans into operational work plans, timelines, and implementation systems.
• Coordinate implementation across multiple work streams including participant recruitment, employer engagement, curriculum delivery, evaluation, communications, operations, and sustainability planning.
• Monitor progress, identify barriers, and ensure successful execution of program goals and grant deliverables.
• Build systems that position Coaches Lab for long-term sustainability and growth.

• Facilitate learning experiences, workshops, coaching sessions, and workforce development activities for youth ages 14-24.
• Build strong relationships with participants and create engaging, supportive learning environments grounded in positive youth development.
• Supervise participant experiences across multiple workforce pathways.
• Support youth in developing communication, teamwork, leadership, critical thinking, problem-solving, and workplace readiness skills.
• Lead implementation and continuous improvement of Urban Initiatives' current and future employer-based learning partnerships.
• Oversee technical implementation partners and consultants supporting workforce pathway delivery.
• Ensure participant experiences reflect Urban Initiatives' commitment to belonging, opportunity, and social-emotional…