CWSP Operations Manager (or Coordinator/Specialist)

Christ the King Jesuit College Prep; Chicago (IL); On-site; USD 40,000 - 65,000; Full time

Job summary

Christ the King Jesuit College Prep is seeking an CWSP Operations Manager/Coordinator/Specialist to oversee transportation for 350–400 interns, plus systems administration and billing duties. The role includes supervising drivers, maintaining route logistics, and supporting Salesforce and data reporting to aid student outcomes.

The position may be titled at Manager/Coordinator/Specialist depending on experience, with a broad salary range and potential schedule variations.

Qualifications

• Bachelor’s degree or an equivalent combination of education and experience.
• Prior experience coordinating transportation at scale and/or serving as a systems administrator, preferred.
• Prior experience working in education, workforce development, nonprofit, social services, or a similar field preferred.
• Proficiency in Microsoft Excel, Word, and PowerPoint.
• A valid driver’s license with no serious moving violations and proof of insurance.
• Minimum of 3 years of safe driving experience and ability to be insured.
• Strong analytical, problem‑solving and organizational skills.
• Respect for the mission of Christ the King Jesuit College Prep.
• Ability to pass Pace driver certification and drug tests.

Responsibilities

• Manage transportation operation for 350–400 students to and from internships.
• Develop and manage routes; create route sheets and coordinate with drivers.
• Supervise van drivers; recruit, train, and evaluate staff.
• Support Salesforce and other systems; generate attendance/timecard reports.
• Set up billing trackers; generate invoices and track payments with the business office.
• Coordinate student break work and payroll/timecard submissions.

Skills

Transportation coordination

Systems administration

Data analytics

Budgeting

Staff supervision

Driver certification

Education

Bachelor’s degree or equivalent

Tools

Microsoft Excel

Microsoft Word

PowerPoint

Job description

CWSP Operations Manager (or Coordinator/Specialist)

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, the 15 years CTK has been open, 100% of CTK graduates have been accepted to college.

Job Summary – Operations Manager

Reporting to the CWSP Director of Student & Partner Success, the CWSP Operations Manager is primarily responsible for transportation, systems administration, partner billing, and student break work. The Manager coordinates the logistics of transporting approximately 350-400 high school students to and from their corporate internships. The Manager drives transportation routes as needed in a backup capacity. Further, the Manager supports the Director in the administration of CWSP’s operational systems (e.g., Salesforce), processes and tracks invoices and payments, and coordinates student work during school breaks. As assigned, the Manager may serve as the Success Coordinator for a limited portfolio of corporate partners and their associated students.

Position Specifics

Level/Title – As written, this is a Manager level role. Depending on the qualifications, experience, and education of the successful candidate, this position could alternately have the level and title of Coordinator or Specialist and the Job Description will be adjusted accordingly.

Schedule – As written, this is a year‑round position. However, depending on the preferences of the successful candidate, this position could work 11 months each year and have a month off each summer or work a reduced schedule each summer.

Salary – The salary for this role will be determined by the level/title, schedule, qualifications, experience, and education of the successful candidate. As such, the salary range for the role is broad – $40,000-$65,000.

Key Responsibilities

CWSP Transportation

• Manage all aspects of CWSP’s transportation operation which safely transports 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 at work. Create and maintain route sheets for drivers that provide 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 are 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.
• 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.

Systems Administrator and Data Analytics

• Support the Director as the system administrator for the school’s instance of Salesforce, which is used to track corporate partners, job placement, and student performance, as well as supplemental systems which are used to support CWSP operations such as the master placement spreadsheet and deployment/attendance tracker.
• Align operational processes with system capabilities and implement workflows that support the most effective and efficient management of CWSP operations and support of students and partners.
• Generate Salesforce reports that support the work of the Student & Partner Success team including, but not limited to, attendance, timecard completion, and student performance.
• Represent CTK in the Cristo Rey Network’s broader database initiatives and lead the implementation of new technology and features at CTK.

Contract Billing

• Set up and maintain the annual billing tracker spreadsheet.
• Generate and send invoices to corporate partners monthly.
• Coordinate with the business office to track payments received.
• Alert the VP for Corporate Work Study when invoices become past due.
• Follow up on all late or missing payments.
• Prepare monthly financial reports for the VP for Corporate Work Study and the business office.

Student Break Work Coordination

• Coordinate student break work (e.g., winter break, spring break, summer break) with the success coordinators, partners, students, families, and the business office.
• Ensure all documentation is complete before students begin work.
• Coordinate timecards and submit payroll to the business office.
• Invoice partners for student work and track receipt of payment.

Other CWSP Duties as Assigned

• Coordinate additional CWSP operations processes and tasks, as assigned.
• Serve as the Success Coordinator for a limited portfolio of corporate partners and their associated students, as assigned.

Requirements

Qualifications

• Bachelor’s degree or an equivalent combination of education and experience.
• Prior experience coordinating transportation at scale and/or serving as a systems administrator, preferred.
• Prior experience working in education, workforce development, nonprofit, social services, or a similar field preferred.
• Proficiency in Microsoft Excel, Work, and PowerPoint.
• A valid driver’s license with no serious moving violations and proof of insurance.
• A minimum of 3 years of safe driving experience and ability to be insured.
• Exceptional analytical and problem‑solving skills with a strong ability to think logically and strategically.
• Meticulous attention to detail, with demonstrated ability to manage complex data sets and route configurations.
• Strong organizational, time management, and administrative skills.
• Respect for the mission of Christ the King Jesuit College Prep.
• Sensitivity to the ethnic, racial, and religious identities of the student body.
• Ability to become and maintain Pace driver certification.
• Ability to pass annual and random drug tests and alcohol screens.
• Flexibility to adjust hours to drive routes as needed and to meet deadlines and school needs.
• Flexibility to work occasional evenings and weekends as needed.

Please note: The successful candidate is required to pass a background check prior to hire and annually while employed, obtain and maintain Pace driver certification, maintain a driver’s record clear of major incidents, and pass annual and random drug and alcohol screenings.