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Assistant Director, Operations - Corporate Study

Job in Chicago, Cook County, Illinois, 60290, USA
Listing for: Christ the King Jesuit College Prep
Apprenticeship/Internship position
Listed on 2026-03-07
Job specializations:
  • Management
  • Transportation
Salary/Wage Range or Industry Benchmark: 125000 - 150000 USD Yearly USD 125000.00 150000.00 YEAR
Job Description & How to Apply Below
Position: Assistant Director, Operations - Corporate Work Study

Christ the King Corporate Work Study Overview

Christ the King Jesuit College Prep, through the Cristo Rey Network model, provides a college preparatory education to high school students from under resourced communities on Chicago’s West Side. At CTK, we prepare students to achieve their fullest potential through the integration of academics, work experience, extracurricular activities, and service. We are proud that, over 15 years, CTK graduates have been accepted to college.

Job Summary – Assistant Director, Operations – Corporate Work Study

CTK seeks an Assistant Director, CWSP Operations, to lead CWSP operations essential to the student experience and success. Reporting to the VP for Corporate Work Study, the Assistant Director, CWSP Operations runs the operational aspects of the CWSP program including, but not limited to, CWSP’s transportation program, job partner contracts and monthly job partner billing, department of labor compliance, student break work, CWSP events, and other operations as assigned.

The Assistant Director drives transportation routes as needed in a back-up capacity.

Key Responsibilities
  • CWSP Transportation:
    Manage all aspects of CWSP’s transportation operation which safely transports approximately 125 students from school to work each morning and from work to school each evening.
  • Develop and manage transportation routes that minimize student time on transportation and maximize student time ate and maintain route sheets for drivers with accurate routes and stop times each day.
  • Manage CWSP’s Pace Not-for-Profit Shuttle Program and all aspects of the Pace van fleet.
  • Manage CWSP’s partnership with a third-party bus transportation company.
  • Ensure operational protocol and procedures are in place and followed to ensure every student arrives at work safely and on-time each morning and every student is picked up and returned to school safely and on-time each evening.
  • Coordinate CWSP mid-day student pick-ups as needed.
  • Driver Supervision:
    Serve as the direct supervisor for CWSP’s van drivers and bus chaperones.
  • Recruit, select, orient, train, and develop staff.
  • Monitor performance, coach, hold accountable, and appraise staff performance.
  • Schedule drivers for all CWSP routes, schedule substitute drivers as needed, and serve as the primary back-up driver/chaperone when driver/chaperone is not available.
  • Manage driver time to most effectively utilize CWSP budget resources.
  • Monitor staff hours, collect timecards, and submit payroll on time each pay period.
  • Contract Billing:
    Maintain accurate records of all corporate partner contracts, contact information, billing amounts, and billing schedules.
  • Send bills to corporate partners on schedule each month.
  • Coordinate with the business office to track payments received.
  • Follow up on all late or missing payments.
  • Prepare monthly financial reports.
  • Student Break Work:
    Lead the student break work for students who work for their CWSP employers during winter, spring, and summer breaks.
  • Work with students, success coordinators, partners, parents, and CTK’s business office to ensure agreements are in place, employment paperwork is complete, direct deposit accounts are set up, supervisors submit timecards, and payroll is complete each period.
  • Department of Labor Requirements:
    Coordinate the process of collecting student’s employment documents (e.g., I-9, W-4).
  • Conduct intake meetings with students and parents/guardians to collect all required documents and coordinate success coordinators in doing the same.
  • Ensure every student is in compliance before they begin work each year.
  • Event Planning and Execution:
    Collaborate with the VP for Corporate Work Study, Director of Corporate Partner Development, and Director of Student and Partner Success to plan and execute CWSP events for students, parents, partners, and the school community.
  • Manage details of the events, including space booking and setup, menu planning and food ordering, communication, RSVP tracking, day of logistics coordination, and assessment.
  • Other CWSP Duties as Assigned:
    Coordinate additional CWSP operations processes and tasks as assigned, including, but not limited to, partner onboarding requirements, daily…
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