Manager - Strategic Initiatives & Apprenticeships

Since 1911, City Colleges of Chicago has been connecting students from across Chicago’s neighborhoods to economic opportunity. By offering a quality education at an unprecedented value, City Colleges provides students and alumni with a pathway to upward mobility. City Colleges of Chicago is the city’s most accessible higher education engine of socioeconomic mobility and racial equity—empowering its students to take part in building a stronger and more just city.

This is a 5-year grant funded position, currently funded through June 30, 2031.

About the Role

Reporting to the Associate Vice Chancellor of Apprenticeship and Workforce Solutions, the Manager-Strategic Initiatives & Apprenticeships is responsible for leading the implementation, administration, and ongoing success of the Chicago Moonshot initiative, a large-scale work-based learning and apprenticeship expansion effort. This position works with key staff and external partners to create access to quality post-secondary education, career and work-readiness training, and paid work-based learning opportunities in IT, Manufacturing, and related industries. The role serves as the primary project manager responsible for the implementation, management, and operational oversight of the Chicago Moonshot initiative.

Responsibilities

• Leads the planning, implementation, and ongoing management of the Chicago Moonshot initiative, coordinating stakeholders and resources to ensure successful execution and achievement of program objectives.
• Organizes and monitors the activities of District Office Workforce Solutions and Centers of Excellence for Tech and Manufacturing teams to ensure alignment with initiative goals, milestones, and timelines.
• Evaluates progress on an ongoing basis and provides Workforce Solutions leadership with project revisions as necessary to achieve established targets.
• Supervises apprentices employed through the initiative, including recruitment, hiring, onboarding, performance management, employee development, discipline, and other supervisory responsibilities as appropriate.
• Oversees apprentice participation throughout the apprenticeship lifecycle by providing coaching, monitoring progress toward training and employment milestones, coordinating with employer partners, addressing barriers to success, and supporting program retention and completion.
• Proactively identifies issues that may impact the successful execution of the initiative, keeps leadership informed of emerging concerns, and develops recommendations to resolve problems and mitigate risk, while identifying creative means of addressing crucial challenges.
• Supports the development of a sustainable model for CCC’s work-based learning programs, working closely with District Office Workforce Solutions and Centers of Excellence for Tech and Manufacturing teams.
• Conducts analyses, prepares presentations, produces reports, memos, and briefs regarding initiative progress, outcomes, and performance.
• Provides reliable, detail-oriented project management expertise to ensure that initiative objectives are achieved and appropriate stakeholders are engaged throughout the process.
• Develops and maintains comprehensive project plans, including necessary inputs, critical stakeholders, milestones, deliverables, timelines, and evaluation plans.
• Manages initiative grant budgets, tracks expenditures, monitors fiscal performance, prepares financial reports, and ensures compliance with funding requirements, organizational policies, and contractual obligations.
• Tracks progress against project and program milestones and collaborates with team members and stakeholders to resolve challenges and overcome barriers.
• Effectively communicates project expectations and updates to team members, leadership, and stakeholders in a timely and effective manner.
• Supports and advises leadership in the development and execution of new strategic initiatives and projects within the scope of this expansion.
• Performs related duties as required.

Qualifications

• A Bachelor’s degree from an accredited college or university in Public Policy, Education, Workforce Development, Business Administration, or a related field required. Master's degree preferred.
• Minimum of four (4) years of progressively responsible program, project, workforce development, apprenticeship, or related management experience, including supervisory responsibility required.
• Experience in higher education, workforce development, career development, or a related field preferred.
• An equivalent combination of education and experience may be considered at the discretion of management, provided the minimum degree requirement is met.
• Demonstrated understanding of work-based learning models preferred.
• Demonstrated supervisory experience, including employee coaching, performance management, and staff development, preferred.
• Demonstrated experience implementing and managing complex, grant-funded initiatives, including budget oversight, compliance monitoring, reporting, and stakeholder engagement.
• Experience leading projects or programs from concept through implementation and evaluation.
• Demonstrated commitment to diversity, equity, inclusion, and student success.
• Strong analytical, critical thinking, and problem-solving skills, with the ability to develop innovative solutions to complex challenges.
• Excellent interpersonal, verbal, and written communication skills, with the ability to build effective relationships across diverse stakeholder groups.
• Strong organizational and project management skills, with the ability to manage multiple priorities, meet deadlines, and adapt to changing needs.
• Strong proficiency in data analysis and reporting using MS Excel and other analytical tools.
• Strong presentation development and communication skills, including using tools such as Microsoft PowerPoint.
• Ability to work effectively in a collaborative, team-based setting and within a culturally diverse environment.
• Proficiency in the use of Microsoft Office (Word, Excel, PowerPoint, and Outlook).

Pay

Salary Range: $80,717 - $85,000. Offered salary will be determined by the applicant's education, knowledge, skills and abilities, as well as other factors such as internal equity.

Benefits

• Excellent health and welfare benefit package and long-term savings and investment programs including 403(b) & 457(b) Investment Plans and a pension plan with the State University Retirement System (SURS) Plan.
• Generous vacation, holiday, personal, and sick days.
• Tuition reimbursement.

For a more detailed overview of benefits, please visit the benefits page of our website.

Additional Information

Chicago residency is required for all full-time employees within 6 months of hire.