Parking Enforcement Supervisor

The Parking Division is seeking a dynamic and customer-focused Parking Enforcement Supervisor to lead the daily operations of the Parking Enforcement Unit. This team plays a vital role in ensuring the safe and accessible use of public streets, sidewalks, parking facilities, and curb space throughout the City of Madison while balancing operational efficiency with quality customer service for residents, visitors, businesses, and partner agencies.

The Supervisor oversees lead workers and enforcement officers who enforce parking regulations across the city. Additionally, this role coordinates operational methods, schedules, routes, and staff assignments while ensuring work meets established quality, timeliness, and performance standards.

Hours: This position is regularly scheduled for 38.75 hours per work. Regular work hours are 7:00 am - 3:30 pm, Monday through Friday; however, hours are flexible and work may be required outside of the regular hours in order to respond to calls that arise and other urgent or emergent issues.

• An effective communicator who provides clear direction, consistent updates, and confident guidance to staff, partner agencies, and the public.

• A steady conflict resolver who can navigate employee issues, performance concerns, and public complaints with fairness and professionalism.

• A growth-minded leader who embraces continuous improvement and supports staff development, training, and evolving operational practices.

• A positive, approachable presence who builds trust through respectful communication, active listening, and a solutions-focused attitude.

• A collaborative supervisor who works effectively across teams,  agencies, and community groups to support coordinated citywide enforcement operations.

IMPORTANT: YOU MUST ATTACH A COVER LETTER IN THE ATTACHMENTS SECTION OF YOUR APPLICATION THAT HIGHLIGHTS YOUR EXPERIENCE RELATED TO THE FOLLOWING: 

1. Leadership experience, including managing or supervising employee groups, serving as a lead worker, and/or leading formal or informal teams;
2. Mediating and resolving conflict involving customers and/or staff;  AND
3. Implementing a workplace process change, including how you identified the need for the change, the steps you took to implement it, and how you managed the change process.

Perform supervision and coordinate daily operations:

• Plan, assign, direct, and review the work of the Leadworkers and Parking Enforcement Officers.
• Develop and coordinate staffing schedules, shift assignments, routes, vacation selections, and daily operational coverage plans.  
• Establish operational priorities and deploy staff resources to address enforcement demands, special events, construction impacts, and emergency situations.
• Monitor field operations for efficiency, timeliness, consistency, safety, and compliance.
• Oversee enforcement activities across multiple shifts, assignments, and geographic areas to maintain effective citywide coverage.
• Interview, recommend for hire, train, supervise, coach, and evaluate enforcement staff.  
• Coordinate onboarding, field training, and employee development activities for enforcement personnel.   
• Address employee performance, attendance, disciplinary, and grievance matters and make recommendations regarding corrective action and personnel decisions.  
• Provide guidance and interpretation regarding parking ordinances, policies, procedures, and enforcement practices for staff.
• Assist in developing, updating, and implementing operational procedures, enforcement guidelines, and workflow improvements.

Respond to issues, concerns and public complaints:

• Provide an active leadership role in the citation review process for contested citations.
• Investigate parking-related concerns and coordinate appropriate follow-up.
• Respond to public complaints and customer service issues related to parking enforcement operations.
• Coordinate with various city agencies to address issues related to signage, traffic control, curb management, and enforcement concerns.
• Work collaboratively with neighborhood groups, businesses, schools, event organizers, and partner agencies on parking and curb access issues.

Coordinate special event parking:

• Coordinate winter parking enforcement operations, snow emergency planning, and seasonal parking regulation enforcement activities.
• Supervise snow emergency enforcement and towing operations.
• Assist with developing and coordinating parking restrictions, traffic control, and towing plans for special events, construction projects, and emergency operations.
• Coordinate temporary parking restrictions, signage placement, staffing assignments, and operational logistics for special events and planned disruptions.
• Assist with developing parking and traffic safety plans for schools, special events, and community activities.

Recommend new equipment and technology:

• Assist with the procurement process for parking enforcement technologies, equipment, and operational tools.
• Monitor the condition, maintenance, replacement, and operational readiness of parking enforcement vehicles and related equipment.
• Maintain uniform, equipment, and operational supply inventories for enforcement staff.
• Assist with budget planning and expenditure tracking related to enforcement equipment, vehicles, uniforms, and operational technology.

Miscellaneous:

•  Assist with responding to Open Records requests and gathering documentation related to parking enforcement activities.
•  Prepare, review, and maintain operational reports, records, training documentation, and program materials.
•  Respond to work-related incidents, accidents, and emergency situations and complete associated documentation and reporting requirements.
•  Provide training, guidance, and technical assistance to City staff and partner agencies regarding parking enforcement procedures and operational practices.

• Four (4) years of experience interpreting, applying, and/or enforcing codes, rules, regulations, ordinances, statutes, laws, restrictions, or workplace policies, procedures, and practices; AND
• Two (2) years of experience applying the following:
  • Map reading, street navigation, or geographic knowledge in field operations, enforcement, or customer service activities;
  • Full range of supervisory principles and practices, which includes staff management, leading operations-related initiatives and training and developing teams;
  • Computer software applicable to the duties of the position, including Microsoft 365.

• Four (4) years of responsible parking enforcement experience comparable to that gained as a Parking Enforcement Officer with the City of Madison; AND
• One (1) year of experience applying the following:
  • Leadership principles (e.g., directing or supervising the work of other staff and/or volunteers, or training, mentoring or coaching)

• Two (2) years of responsible parking enforcement experience comparable to that gained as a Parking Enforcement Officer with the City of Madison, including at least one (1) year of applying leadership principles (e.g., directing or supervising the work of other staff and/or volunteers, or training, mentoring or coaching); AND
• Associate's (or higher level) degree in Business Administration, Criminal Justice, or a closely related field .

• Possession of a valid driver’s license.
• Must obtain Basic TIME (Transaction Information for the Management of Enforcement) certification within six (6) months of hire and must be re-certified every two (2) years. Because of this certification, candidates must undergo a thorough background check including fingerprints, and will be disqualified based on FBI guidelines.
• The employee may be expected to attend meetings at various locations, including meetings outside regular work hours, including nights and weekends.
• The employee must be able to work a flexible schedule in order to meet with staff, attend meetings, and cover absences, special events, and snow emergencies.

• Ability to efficiently travel throughout the City in order to review parking complaints or concerns, review signage issues, and assist with enforcement actions.
• Ability to walk extended distances in all types of weather, when performing field observations.
• Ability to carry objects weighing up to 20 pounds.
• Ability to bend, lift, reach, and pound signs, as necessary.
• Ability to work outdoors in all types of weather at various times of day and night.

Salary : $79,210 - $93,997