Toll Collection Assistant Supervisor at City of Chesapeake Human Resources – Chesapeake, Virginia
City of Chesapeake Human Resources
Chesapeake, Virginia, 23322, United States
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Industries:Government/Civil ServiceJob Function:Admin/Clerical/Secretarial
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About This Position
Working Title of Vacant PositionToll Collection Assistant Supervisor
Job Type: Full Time
Posting Type: Public
Number of Vacancies: 1
Department: PUBLIC WORKS
Division: PUB WORKS 168 TOLL ROAD
Requisition Number: 20263
Number of hours worked per week: 40, mandatory overtime may be required
Work Schedule: Normal Shift Hours: 2:30pm-11:00pm Schedules are subject to change when needed to support a 24 hour facility. Employees may be expected to work hours in excess of, and/or outside of, their normally scheduled hours in response to short-term department needs and/or City-wide emergencies. Emergency operations support work and work locations may be outside of normal job duties. | Continuously- 2/3 or more of the time.
Work Site Location: Chesapeake, VA
Position Driving Requirement: O - Occasional
Pay Basis: Semi-Monthly
Advertised Salary:
Job Description:
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.
Required Qualifications:
Preferred Qualifications:
Job Open Date: 04/02/2026
Job Close Date: 04/17/2026
Open Until Filled: No
Special Instructions to Applicants:
Job Type: Full Time
Posting Type: Public
Number of Vacancies: 1
Department: PUBLIC WORKS
Division: PUB WORKS 168 TOLL ROAD
Requisition Number: 20263
Number of hours worked per week: 40, mandatory overtime may be required
Work Schedule: Normal Shift Hours: 2:30pm-11:00pm Schedules are subject to change when needed to support a 24 hour facility. Employees may be expected to work hours in excess of, and/or outside of, their normally scheduled hours in response to short-term department needs and/or City-wide emergencies. Emergency operations support work and work locations may be outside of normal job duties. | Continuously- 2/3 or more of the time.
Work Site Location: Chesapeake, VA
Position Driving Requirement: O - Occasional
Pay Basis: Semi-Monthly
Advertised Salary:
Starts at $38,579; Depending on qualifications and experience.
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:
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:
- Wil be required to successfully train as a toll collector.
- Will be required to work as a toll collector as needed.
- 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.
Required Qualifications:
VOCATIONAL/EDUCATIONAL REQUIREMENT: Requires high school diploma or GED/HSE and any combination of education and experience equivalent to satisfactory completion of one year of college education.
EXPERIENCE REQUIREMENT: In addition to satisfying the vocational/education standards, this class requires a minimum of six months of related, full-time equivalent experience.
SPECIAL CERTIFICATIONS AND LICENSES: Requires a valid driver’s license and a driving record that is in compliance with City Driving Standards.
SPECIAL REQUIREMENTS: Employees may be expected to work hours in excess of their normally scheduled hours in response to short-term department needs and/or City-wide emergencies. Emergency operations support work and work locations may be outside of normal job duties.
EXPERIENCE REQUIREMENT: In addition to satisfying the vocational/education standards, this class requires a minimum of six months of related, full-time equivalent experience.
SPECIAL CERTIFICATIONS AND LICENSES: Requires a valid driver’s license and a driving record that is in compliance with City Driving Standards.
SPECIAL REQUIREMENTS: Employees may be expected to work hours in excess of their normally scheduled hours in response to short-term department needs and/or City-wide emergencies. Emergency operations support work and work locations may be outside of normal job duties.
Preferred Qualifications:
- One or more year of supervisory experience
- Cash handling experience
- Experience developing schedules for multiple employees and multiple shifts
- One or more years’ experience in Toll Operations preferred
- Strong customer service
- Microsoft office
Job Open Date: 04/02/2026
Job Close Date: 04/17/2026
Open Until Filled: No
Special Instructions to Applicants:
Chesapeake Expressway Toll Collection Assistant Supervisor’s work as essential (alpha) personnel in support of a 24 hour/day, 365-day/year operation, including holidays, weekends and during inclement weather events. Schedules are subject to change to meet the operational needs of the Chesapeake Expressway.
Medical marijuana:
In accordance with City policy, this position is deemed safety sensitive. As such, applicants for this position are subject to pre-employment drug/alcohol testing after receiving a conditional offer of employment and may also be subject to random testing. This drug test includes testing for marijuana. Possession of a medical marijuana card will not excuse an applicant from the testing process; however, a test will not be considered positive for marijuana if a valid medical marijuana certification is presented unless the position requires a commercial driver’s license (CDL) or is a sworn law-enforcement officer/deputy.
Medical marijuana:
In accordance with City policy, this position is deemed safety sensitive. As such, applicants for this position are subject to pre-employment drug/alcohol testing after receiving a conditional offer of employment and may also be subject to random testing. This drug test includes testing for marijuana. Possession of a medical marijuana card will not excuse an applicant from the testing process; however, a test will not be considered positive for marijuana if a valid medical marijuana certification is presented unless the position requires a commercial driver’s license (CDL) or is a sworn law-enforcement officer/deputy.
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Job Location
Chesapeake, Virginia, 23322, United States
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