Assistant Manager, Tolling Operations in Chicago, Illinois at Skyway Concession Company

About the Skyway

Built by the City of Chicago in 1958, the Chicago Skyway Toll Bridge (“Skyway”) is a 7.8-mile toll road connecting the Indiana Toll Road to the Dan Ryan Expressway on Chicago’s South Side.

A key feature of the Skyway is the half-mile-long steel truss “High Bridge,” which spans the Calumet River and Calumet Harbor—an important route for industrial shipping. The bridge’s main span is 650 feet long and provides 125 feet of vertical clearance.

Our Vision: To be the best operational toll road project in the United States, recognized for delivering exceptional value to our customers, partners, and community through operational excellence and sustainable long-term performance.Our Mission: Our mission is simple: Provide the safest, most time-efficient, convenient, and reliable highway to and through Chicago

Position Summary

The Assistant Manager, Tolling Operations provides leadership and oversight to 4-5 Tolling Operations Supervisors and oversees the Traffic Management Center (TMC) operations in support of safe, efficient, customer-focused, and reliable tolling service. The TMC serves as the central point for monitoring roadway, toll plaza, traffic, and operational conditions across the Skyway. TMC Operators maintain real-time situational awareness; receive, document, and communicate operational information; coordinate first-line responses to incidents, equipment failures, lane disruptions, severe weather, and other abnormal conditions; dispatch or notify appropriate internal teams, emergency responders, and vendors; and escalate significant events through established protocols. The TMC also supports continuity of operations by maintaining accurate incident records, tracking response actions, communicating status updates, and helping ensure that tolling and roadway operations remain safe, reliable, and coordinated on a 24/7 basis. The role manages workforce and resource planning, service delivery, operational performance, cost control, safety, compliance, operational-control coordination, incident response, and continuous improvement. The Assistant Manager supports the SCC Supervisor Life Cycle from selection and onboarding through development, performance, succession, and transition, while reinforcing SCC’s Supervisory Skills Framework across Foundation, Managing People, Managing Operations, and Advanced Leadership. The position supports a 24/7 operating environment and may act for the Director of Tolling & Field Systems when assigned.

Essential Functions (Duties and Responsibilities)

1. Tolling Operations Leadership

Provide day-to-day leadership and direction to Tolling Operations Supervisors and support consistent execution of tolling operations.Monitor operational performance, staffing, service levels, transaction activities, and departmental priorities.Ensure toll lanes, TMC operations, and related tolling activities are appropriately staffed and operational.Support timely resolution of operational issues, equipment concerns, system issues, customer matters, and other tolling-related disruptions.Partner with Operations and HR leadership and other departments to maintain effective and reliable tolling operations.

Maintain and periodically test Tolling Operations emergency-response and business-continuity procedures, including staffing contingencies, manual or degraded-mode operations, severe-weather response, communication protocols, and post-incident review. Ensure supervisors and TMC Operators understand their assigned roles and that identified corrective actions are documented and completedParticipate in an on-call leadership rotation and remain available for escalated incidents, staffing emergencies, severe weather, special events, and other operational disruptions.Ensure customer interactions and tolling services reflect SCC expectations for safety, reliability, professionalism, and timely issue resolution.2. Supervisory Leadership & Development

Lead, coach, and develop Tolling Operations Supervisors to strengthen leadership, accountability, communication, and operational performance.Set clear expectations and hold supervisors accountable for performance, attendance, conduct, safety, and adherence to SCC policies and procedures.Support supervisors in managing employee performance, employee concerns, training, and day-to-day employee relations matters.Partner with Human Resources on talent management, performance management, staffing, employee relations, and other people-related matters.Promote consistent and fair application of SCC policies, procedures, and labor requirements.Build supervisor capability through structured onboarding, mentoring, recurring training, coaching, and documented development plans.Ensure supervisors and TMC Operators complete required onboarding, job-specific training, safety instruction, system training, and periodic refresher requirements. Maintain visibility into qualification status, address training gaps, and verify operational readiness before employees assume independent responsibilities.3. Workforce & Resource Management

Review staffing needs and support workforce planning to ensure appropriate operational coverage.Oversee scheduling practices and resource allocation through the Tolling Operations supervisory team.Monitor staffing levels, attendance, overtime, and operational coverage and communicate significant trends or concerns to Operations leadership.Identify opportunities to improve workforce utilization, operational efficiency, and service delivery.4. Budget & Financial Responsibility

Monitor and track Tolling Operations costs and provide information to Operations leadership to support budget management.Monitor overtime, staffing-related costs, supplies, and other operational expenditures within assigned areas of responsibility.Support the development and management of departmental budgets and identify cost-saving opportunities.Review operational variances and work with appropriate departments to understand and address cost or revenue-related issues.Promote responsible use of Company resources while maintaining operational and service standards.Lead the operational response to suspected cash loss, revenue leakage, fraud, policy violations, or control breakdowns within Tolling Operations. Preserve relevant records, coordinate promptly with Finance, Audit, Human Resources, Security, and legal counsel as appropriate, and track corrective actions through resolution5. Performance, Reporting & Continuous Improvement

Review operational reports and key performance information to identify trends, issues, and opportunities for improvement.Ensure supervisors maintain accurate operational records, reports, schedules, and documentation.Prepare or contribute to departmental reports and management updates.Identify opportunities to improve processes, procedures, technology utilization, and operational efficiency.Support implementation of operational improvements and monitor results.6. Safety, Compliance & Risk Management

Promote and reinforce SCC’s safety expectations throughout Tolling Operations.Ensure supervisors and employees follow applicable safety practices, policies, procedures, and operational requirements.Identify operational risks and work with leadership and appropriate departments to address them.Support compliance with applicable laws, regulations, SCC policies, procedures, and the current Collective Bargaining Agreement (CBA).Ensure appropriate documentation and escalation of significant operational, safety, employee, or compliance matters.

7. Cross-Functional & Vendor Coordination

Partner with Human Resources, Finance, IT, Customer Service, Audit, Maintenance, and other departments to support effective Tolling Operations.Coordinate with IT and other technical teams regarding tolling systems, equipment, system issues, and operational disruptions.Coordinate first-line operational response, escalation, and documentation for tolling-system outages, lane-equipment failures, degraded operations, and business-continuity events.Partner with Audit and Finance on toll revenue reconciliation, shortages, investigations, and related operational matters.Monitor adherence to cash-handling, revenue-control, exception-processing, reconciliation, and record-retention procedures; promptly escalate discrepancies in accordance with SCC requirements.Support vendor relationships and operational issues within assigned areas of responsibility.Promote effective communication and collaboration across departments.8. Leadership Decision-Making

Make timely operational decisions within established authority and escalate matters requiring higher-level review.Evaluate operational information, employee and customer impacts, financial considerations, safety concerns, and business priorities when making decisions.Provide recommendations to upper management regarding staffing, performance, resource needs, operational risks, and process improvements.Serve as a leadership resource for Tolling Operations Supervisors and promote consistent decision-making across the department.Qualifications

Bachelor’s degree in Business Administration, Operations Management, Transportation/Logistics, Management, Engineering or a related field; or an equivalent combination of relevant education, logistics/tolling/transportation experience, and progressively responsible leadership experience.5-7 years of progressively responsible experience in tolling, transportation operations, customer operations, or a comparable 24/7 operational environment, including supervisory or team-lead responsibility.

Supervisory or team-lead experience with responsibility for people, operations, or resources.Experience working in a structured operational environment with established policies, procedures, and performance expectations.Demonstrated ability to lead, coach, and hold employees accountable.Strong organizational, communication, and problem-solving skills.Proficiency with Microsoft Office and the ability to learn and use tolling, workforce-management, incident-management, reporting, and other applicable business systems.Ability to work collaboratively with multiple departments and respond effectively to operational issues.Ability to work in a unionized environment and apply policies and procedures consistently.Demonstrated commitment to customer service, safety, reliability, continuous learning, and cross-functional teamwork.Experience in tolling, logistics, transportation, roadway, infrastructure, or a similar operational environment.Experience supervising supervisors or leading a multi-level operational team.Experience with budget monitoring, cost tracking, workforce planning, or operational reporting.Experience working with tolling systems, revenue operations, TMC operations, or related technology.Additional leadership training or professional certification.Experience with process improvement and operational performance management.

Knowledge, Skills, Abilities & Competencies

Operational Leadership – Ability to manage competing priorities and maintain effective daily operations.People Leadership – Ability to coach, develop, motivate, and hold supervisors accountable.

Decision-Making – Uses sound judgment and available information to make timely operational decisions.Communication – Communicates clearly and effectively with employees, supervisors, leaders, and cross-functional partners.Problem-Solving – Identifies issues, evaluates options, and implements practical solutions.Financial Stewardship – Understands operational costs and uses Company resources responsibly.Safety & Risk Awareness – Promotes safe practices and identifies operational risks.Collaboration – Works effectively across departments and with internal and external partners.Integrity & Accountability – Demonstrates dependability, professionalism, integrity, and commitment to SCC’s values.

Work Environment & Physical Demands

This position operates in office, control-room, toll-plaza, and roadway-adjacent operational environments. While performing the duties of this role, the employee is regularly required to communicate, sit, stand, walk, and use standard office and operational equipment.

The role requires periodic presence in operational areas, including work around live traffic and exposure to outdoor weather conditions, noise, and temperature changes. The employee must be able to respond to operational needs across shifts, including nights, weekends, holidays, and emergency situations. Occasional lifting up to 25 pounds, climbing stairs, and extended walking or standing may be required.

Reasonable accommodation may be made to enable individuals with disabilities to perform the essential functions of this position.

Risk, Health, Safety, Environment & Quality

All employees are expected to carry out their duties in alignment with SCC’s commitment to safety, stewardship, and regulatory compliance. Employees must follow established health and safety practices, immediately report hazards, and actively support a safe, secure, and environmentally responsible workplace.

The Assistant Manager is expected to actively promote safety leadership, risk awareness, operational quality, and compliance throughout Tolling Operations.