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Toll Collection Assistant Supervisor

Chesapeake, VA

Job Description

Toll Collection Supervisors are essential personnel responsible for managing toll collection activities of eight to fourteen Toll Plaza lanes and directly supervise Toll Collectors, part-time employees, and Temps at the Chesapeake Expressway, which operates 24 hours per day, 7 days per week, 365 days per year.

Toll Collection Assistant Supervisors are typically assigned to oversee and assist with all three shifts. Toll Collection Assistant Supervisors work Sunday through Thursday are scheduled 8-hour workdays, but schedules are subject to change to meet operational needs.

Toll Collection Assistant Supervisor's duties and responsibilities include but are not limited to the following:

  • Schedule staff and create lane assignments to ensure that the appropriate number of lanes are open to meet traffic demands in a safely.
  • Promote and ensure quality customer service, which may require interaction with difficult customer service situations.
  • Promote and ensure the safety of all staff members and customers.
  • Train and direct employees on all policies and procedures.
  • Update and distribute materials and operating manuals.
  • Evaluate subordinates' performance and provide constant feedback.
  • Counsel subordinates on disciplinary actions as needed and document such occurrences.
  • Maintain change fund accurately and keep funds secure.
  • Prepare, distribute and collect individual toll collector change funds, including delivering change to toll booths.
  • Monitor the toll facility and grounds constantly for unusual occurrences, safety concerns, traffic and unauthorized personnel.
  • Monitor Milestone (surveillance system) and ARCS/RTM (toll system) for statuses and potential issues.
  • Troubleshoot and make necessary adjustments to equipment, includes repositioning toll gates.
  • Inspect the plaza and roadway for debris and remove debris, includes placing/removing cones and barrels.
  • Access, print, evaluate reports and prepare reports, including accident/incident reports, performance reports, traffic reports and other reports as requested.
  • Use Kronos (timekeeping system) to enter schedules, enter adjustments and comments, grant or deny time off requests, review leave accruals and approve timecards.
  • Track and report time worked by temporary staff.
  • Ensure that all emergency conditions (injury, damage to property, fire, medical, etc.) are handled immediately and safely and reported to the appropriate parties.
  • Provide notification and reports to management regarding operations, unusual occurrences, personnel issues, traffic flow, emergency situations, etc.
  • Assume additional responsibilities/duties as required by management.

In addition, Toll Collection Supervisors must possess strong written and oral communication skills and strong organizational skills. Toll Collection Supervisors must also be able to climb stairs, move around the toll plaza and are required to safely perform their duties around fast-moving vehicles and other hazards.

The City of Chesapeake offers an exceptional range of benefits. Please browse our Benefits Brochure, for a full list of benefits and employee perks. PDN-9f2e5882-cd1f-41e5-8ca4-8c1ff1be837d
Toll Collection Supervisors are essential personnel responsible for managing toll collection activities of eight to fourteen Toll Plaza lanes and directly supervise Toll Collectors, part-time employees, and Temps at the Chesapeake Expressway, which operates 24 hours per day, 7 days per week, 365 days per year.

Toll Collection Assistant Supervisors are typically assigned to oversee and assist with all three shifts. Toll Collection Assistant Supervisors work Sunday through Thursday are scheduled 8-hour workdays, but schedules are subject to change to meet operational needs.

Toll Collection Assistant Supervisor's duties and responsibilities include but are not limited to the following:

  • Schedule staff and create lane assignments to ensure that the appropriate number of lanes are open to meet traffic demands in a safely.
  • Promote and ensure quality customer service, which may require interaction with difficult customer service situations.
  • Promote and ensure the safety of all staff members and customers.
  • Train and direct employees on all policies and procedures.
  • Update and distribute materials and operating manuals.
  • Evaluate subordinates' performance and provide constant feedback.
  • Counsel subordinates on disciplinary actions as needed and document such occurrences.
  • Maintain change fund accurately and keep funds secure.
  • Prepare, distribute and collect individual toll collector change funds, including delivering change to toll booths.
  • Monitor the toll facility and grounds constantly for unusual occurrences, safety concerns, traffic and unauthorized personnel.
  • Monitor Milestone (surveillance system) and ARCS/RTM (toll system) for statuses and potential issues.
  • Troubleshoot and make necessary adjustments to equipment, includes repositioning toll gates.
  • Inspect the plaza and roadway for debris and remove debris, includes placing/removing cones and barrels.
  • Access, print, evaluate reports and prepare reports, including accident/incident reports, performance reports, traffic reports and other reports as requested.
  • Use Kronos (timekeeping system) to enter schedules, enter adjustments and comments, grant or deny time off requests, review leave accruals and approve timecards.
  • Track and report time worked by temporary staff.
  • Ensure that all emergency conditions (injury, damage to property, fire, medical, etc.) are handled immediately and safely and reported to the appropriate parties.
  • Provide notification and reports to management regarding operations, unusual occurrences, personnel issues, traffic flow, emergency situations, etc.
  • Assume additional responsibilities/duties as required by management.

In addition, Toll Collection Supervisors must possess strong written and oral communication skills and strong organizational skills. Toll Collection Supervisors must also be able to climb stairs, move around the toll plaza and are required to safely perform their duties around fast-moving vehicles and other hazards.

The City of Chesapeake offers an exceptional range of benefits. Please browse our Benefits Brochure, for a full list of benefits and employee perks. PDN-9f2e5882-cd1f-41e5-8ca4-8c1ff1be837d

About City of Chesapeake

Chesapeake, Virginia is a vibrant community that enjoys the best of two worlds, one of urban variety, culture, and excitement, and another of rural landscapes and relaxed living. 

Located 20 minutes from the oceanfront, 15 minutes from downtown Norfolk, and 45 minutes from Colonial Williamsburg and the Outer Banks of North Carolina, Chesapeake is the perfect place in which to live, work, and raise a family. 

Home to beautiful parks, lakes, and rivers, Chesapeake has more miles of deepwater canals (part of the Intracoastal Waterway) than any other city in the country! 

The City of Chesapeake was formed through the merger of the City of South Norfolk and Norfolk County in 1963. It’s a community of communities, with each having its own distinctive history. 

Over the last decade, many national and international companies have taken advantage of the City’s ports, atmosphere, and highly qualified labor market by relocating to Chesapeake. 

Chesapeake’s neighborhoods offer a variety of comfortable housing alternatives, from apartments and town homes, to single-family residences and executive homes. The City is consistently ranked by the FBI as one of the safest U.S. cities (with populations over 150,000), which lends to the safe, community atmosphere that residents enjoy.

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Toll Collection Assistant Supervisor
City of Chesapeake
Chesapeake, VA
Jun 18, 2025
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