Executive Director (Chicago)

Reports to : Chief Executive Officer Member of : Senior Leadership Team (SLT)

About Us :

We are a 25-year-old nonprofit workforce development organization dedicated to preparing individuals from underserved communities for rewarding careers in technology. With a passionate team of 35+ professionals, we’re committed to bridging the gap between diverse talent and the tech industry. We find talent, train talent, and place talent in rewarding careers that end cycles of generational poverty and yield long-term success. At our core, we believe that innovation thrives when people are empowered, supported, and allowed to grow.

If you’re someone who is energized by people‑first leadership and is passionate about making a lasting impact, you may want to be a part of our journey as we continue to shape the future of tech professionals.

About the Role :

The Executive Director (ED) will lead the i.c.stars Chicago program, ensuring its effectiveness throughout the program participant journey—starting with recruitment, through program delivery, graduate placement, and career retention. The ED manages a team of 5–7 full‑time staff, leverages a local advisory board, and collaborates with the national team to align local efforts with organizational goals.

Reporting to the Chief Executive Officer, the ED will oversee all aspects of the program in addition to corporate engagement and funding strategies to sustain impact. The role requires a leader with high emotional intelligence who can cultivate long‑term relationships, drive program excellence, and steward financial and external engagement—activating key stakeholders as doers, donors, and door openers to strengthen i.c.stars’ position as a leader in workforce development with a mission to transform people, businesses, and communities.

Key Responsibilities

Leadership & Program Execution

Execute and implement the strategic vision for i.c.stars Chicago ensuring alignment with goals and sustainable growth.

Lead and develop a high‑performing team, overseeing key staff who own program areas, including corporate sponsorship and events, talent placement, recruitment, case management, technology and program facilitation.

Ensure operational excellence and program effectiveness, driving strong execution across training, alumni engagement, and employer partnerships.

Manage local program operations, personnel, and financial performance, ensuring programmatic and budgetary alignment with organizational priorities.

Ensure high‑quality delivery of our training model to i.c.stars program participants

Support the implementation of data‑driven performance metrics, tracking program outcomes, placement rates, and fundraising effectiveness.

Lead operational planning efforts, ensuring seamless coordination between finance, marketing, development, and program teams.

Engage the local advisory board, leveraging their expertise to expand employer relationships and fundraising success.

Lead efforts to recruit, develop, and engage a high‑impact local advisory board, leveraging their expertise and networks to drive mission success.

Cultivate and manage strategic community‑based partnerships with local nonprofits, workforce development agencies, and educational institutions to expand program impact.

Expand the organization’s influence within the Chicago technology ecosystem, strengthening community partnerships and industry engagement.

Advance i.c.stars' thought leadership by representing the organization at high‑profile industry events, conferences, and workforce development panels, emphasizing our mission to connect potential with opportunity and revolutionize access to technology careers.

Support the optimization efforts of systems and processes that enhance efficiency, scalability, and data‑driven decision‑making.

Monitor and analyze workforce trends, including evolving business, leadership, and technology skill demands, to enable i.c.stars to continuously refine program offerings and employer engagement strategies.

Support a diverse funding portfolio, including corporate partnerships, foundation grants, individual donors, and government funding, ensuring alignment with annual revenue targets.

Manage the local P&L and financial performance, ensuring budgetary discipline while maximizing program impact.

Secure corporate partnerships and engagement opportunities, such as executive volunteer programs, mentorship initiatives, and industry sponsorships.

Identify and cultivate employer partnerships to drive hiring opportunities for i.c.stars graduates, ensuring strong workforce demand for program participants.

Lead and support events and networking conferences, positioning i.c.stars as a premier organization in the tech workforce development space.

Collaborate with the National Development Team to enhance grant strategy, proposal development, and impact storytelling for funders.

Perform other duties as required to support the goals and mission of i.c.stars.

What You Bring :

Bachelor’s degree in Business, Human Resources, Workforce Development, Technology, or a related field, OR equivalent experience

5+ years of experience managing high performing teams, business development, talent placement, workforce development, business operations, or a related field, with at least 3 years in a leadership or strategic role.

Expertise in workforce development strategies and emerging industry trends that influence bridging education and employment.

Exceptional interpersonal skills; ability to effectively collaborate with internal and external stakeholders at all levels.

Strong operational and financial acumen, including budgeting, forecasting, and P&L oversight.

Experience leveraging data and analytics to drive strategic decisions and optimize program outcomes.

Excellent interpersonal and relationship‑building skills.

Demonstrated success identifying and cultivating new corporate and / or foundation funders and partners

Familiarity with workforce development principles and local ecosystem.

Proven capacity to navigate corporate, municipal, and philanthropic landscape

Inclusive philosophy with experience working with ethnically and socioeconomically diverse communities

Demonstrated capacity to build,manage, support and retain collaborative, positive and high performing team culture

Exceptional interpersonal skills; ability to effectively collaborate with internal and external stakeholders at all levels

Strong communication, presentation, and writing skills

Experience in workforce development, talent acquisition, and human resources a plus

Strong analytical and problem‑solving skills

Why Join Us?

Make an Impact : Help us shape the team that develops and prepares individuals for careers in tech. Be a part of an organization that’s making a meaningful difference in the lives of our participants, and the communities and businesses we serve.

Growth Opportunities : We’re a dynamic, growing organization that’s committed to developing both our staff and the people we serve. You’ll have the chance to shape your role and grow professionally.

Collaborative Environment : We pride ourselves on being a supportive, team-oriented organization where everyone’s voice is heard.

Work‑Life Balance : We value our people’s well‑being, offering flexible work arrangements and a comprehensive benefits package.

A Culture of Learning : As a team, we believe in continual growth—personally and professionally. There’s always room to learn, share ideas, and try something new.

• i.c.stars is committed to delivering an equitable compensation and benefits package to support the financial, mental, and physical wellness of our staff. Benefits include :
• Health Insurance (i.c.stars covers 95% of individual medical plan premiums)
• 401(k) plan with employer match
• Flexible Spending Account (FSA)
• Life Insurance & Disability Coverage
• Generous Paid Time Off & Company Holidays
• Professional Development Opportunities

If you meet the qualifications described above and are excited about creating a people‑centric culture and driving the development of our talented team, we welcome your application.

i.c.stars is an equal opportunity employer. All qualified applicants will be considered for employment without unlawful discrimination based on race, color, creed, national origin, sex, age, disability, marital status, sexual orientation, military status, prior record of arrest or conviction, or current employment status.

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