Executive Director of Strategic Initiatives

EXECUTIVE DIRECTOR OF STRATEGIC INITIATIVES

HAROLD WASHINTON COLLEGE

CITY COLLEGES OF CHICAGO

City Colleges of Chicago’s vision is to be recognized as the city’s most accessible higher education engine of socioeconomic mobility and racial equity – empowering all Chicagoans to take part in building a stronger and more just city. The community college system’s more than 3,500 faculty and staff serve more than 70,000 students annually at seven colleges and five satellite sites.

Reporting to the President of a college, the Executive Director – Strategic Initiatives plays a key leadership role in advancing the college’s vision, mission, and strategic goals. The Executive Director – Strategic Initiatives is responsible for providing strategic direction and administrative oversight across multiple areas of the college, including academic, operational, and organizational excellence. The Executive Director leads the successful execution of major projects, managing all phases from planning and resource allocation to coordinating efforts among college teams, district personnel, and external stakeholders.

The role ensures projects are completed on time and in alignment with the college’s strategic objectives. Performs related duties as required.

• Spearheads the identification and implementation of initiatives that enhance student success, streamline operations and improve organizational effectiveness, aligning efforts with the college’s long-term strategic objectives.
• Leverages internal and external best practices to drive continuous improvement across academic and administrative functions, ensuring the integration of innovative solutions that advance the institution’s mission.
• Collaborates with senior leadership to design and refine organizational processes and procedures that optimize performance across the college.

• Directs and manages multiple cross-functional project teams, guiding them through all phases of project execution from ideation and resource planning to implementation and post-project review.
• Uses a data-driven, hypothesis-based approach to foster a solution-oriented mindset within teams, establishing clear metrics to measure both team and project performance while ensuring accountability for outcomes.
• Coaches, mentors, and develops Project Team Leaders, providing guidance on advanced problem-solving techniques, performance management and leadership development.
• Leads the recruitment, evaluation, and professional development of project leadership, making decisions regarding staffing, performance improvement, and, when necessary, disciplinary action.
• Resolves conflicts and challenges across teams and stakeholders, ensuring smooth collaboration and maintaining focus on project goals.

• Establishes performance metrics to measure the impact of projects, tracks milestones, and ensures timely delivery in alignment with success criteria.
• Proactively identifies risks, manages scope changes, and implements mitigation strategies to keep projects on track.
• Conducts post-project reviews to assess outcomes and generate recommendations for continuous improvement.

• Serves as a key liaison with internal and external stakeholders, maintaining clear and timely communication on project expectations, progress, and results.
• Prepares and delivers proposals, status updates and presentations, ensuring transparency and alignment with project goals.
• Works collaboratively with department heads and other senior leaders to allocate resources, resolve interdepartmental issues, and ensure the success of cross-functional initiatives.
• Cultivates and strengthens relationships with key stakeholders, both within and outside the institution, to support the successful delivery of strategic projects and initiatives.

Reports To:

College President

Direct Supervision:
None

Indirect Supervision:
Project Team Leaders

• Masters degree from an accredited college or university in Education, Administration, Business, or related…