Lead Director, Workforce Development

Urban Initiatives • Chicago, IL

6d • Hybrid

About The Position

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 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?

Requirements

• Passion for Urban Initiatives' mission and commitment to youth development.
• Bachelor's degree required.
• Minimum of five years of experience working directly with youth, preferably ages 14-24.
• Experience leading youth development, workforce development, employment, mentoring, leadership, or career readiness programs.
• Demonstrated ability to build strong relationships with young people and facilitate engaging learning experiences.
• Experience supervising staff and managing program implementation
• Strong project management and organizational skills with the ability to manage multiple priorities.
• Demonstrated ability to coordinate cross-functional teams and move complex initiatives from planning through implementation.
• Excellent written, verbal, and interpersonal communication skills.
• Commitment to inclusion and positive youth development practices.
• Ability to work occasional evenings and weekends as program activities require.

Nice To Haves

• Experience building partnerships with employers, industry partners, higher education institutions, schools, community organizations, or public agencies.
• Bilingual English/Spanish fluency preferred.

Responsibilities

• 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 development.
• Partner with the Director of Curriculum and Learning to adapt and implement participant learning experiences.
• Partner with the Director of Data Infrastructure to build evaluation, reporting, and continuous improvement systems.
• Partner with the Lead Director of Partnerships to develop employer engagement strategies and expand workforce pathways.
• Partner with the Operations team to design and manage participant onboarding, stipend payments, compliance, credential tracking, and operational systems that support a high-quality participant experience.
• Collaborate with leaders across Coach for Success, Community Member to Coach, Summer Employment, and other workforce initiatives to strengthen participant pathways and eliminate duplication.
• Align external workforce development initiatives with Urban Initiatives' internal talent strategy, ensuring workforce pathways strengthen both participant outcomes and the organization's long-term staffing pipeline.
• Convene cross-functional teams, align priorities, and leverage organizational expertise to deliver a cohesive work-based learning model.
• Develop relationships with employers, industry partners, higher education institutions, community organizations, and public agencies.
• Coordinate work-based learning opportunities including job shadows, site visits, mentoring experiences, internships, and career exploration opportunities.
• Expand employer partnerships across coaching, healthcare, sports business, event operations, and emerging career sectors.
• Support the development of sustainable employer engagement strategies that create long-term opportunities for young people.
• Represent Urban Initiatives within workforce development and youth employment networks.
• Provide strategic leadership for Urban Initiatives' evolving work-based learning portfolio.
• Identify opportunities to strengthen alignment across current and future workforce development partnerships and initiatives.
• Recommend improvements to Urban Initiatives' workforce development strategy based on implementation experience, participant outcomes, and employer feedback.
• Partner with executive leadership to shape the long-term vision for work-based learning within Urban Initiatives.

Benefits

• Competitive medical, dental, and vision insurance options.
• Paid time off and a generous holiday schedule.
• Opportunities for professional learning and leadership development.
• The opportunity to build a nationally recognized workforce development model from the ground up.
• Work alongside an experienced leadership team committed to innovation, continuous learning, and investing in people.
• A mission-driven team committed to helping Chicago's young people thrive through the power of sport, play, and meaningful career pathways.
• Teamwork and Inclusion

What This Job Offers

• Job Type: Full-time
• Career Level: Director