Parking Enforcement Supervisor - Winnipeg

Reimagined Parking Inc.; Winnipeg; Hybrid; CAD 28,000 - 30,000; Full time

Benefits offered by this job

Employee Assistance Program

Paid Vacation

Job summary

Reimagined Parking Inc. is seeking a Parking Enforcement Supervisor in Winnipeg to lead field officers and ensure compliance with parking regulations. You will manage schedules, handle escalated issues, and partner with other departments to improve services.

The role emphasizes training, performance reviews, and implementing policies to increase efficiency and effectiveness of the parking program. A valid driver’s license is required.

Qualifications

• Minimum 3–5 years of experience in parking enforcement, law enforcement, or public safety, with 1–2 years in a supervisory role.
• Strong knowledge of local parking regulations and enforcement procedures.
• Excellent leadership, communication, and interpersonal skills.
• Ability to manage schedules and supervise field staff.
• Proficiency with enforcement technology and related software tools.

Responsibilities

• Supervise parking enforcement officers and monitor KPI metrics.
• Audit adherence to department policies and procedures.
• Identify performance issues and provide evidence to the Enforcement Manager weekly.
• Coordinate field operations and report on enforcement activities.
• Assist in developing and implementing enforcement strategies and SOPs.

Skills

Leadership

Communication

Parking enforcement

Enforcement technology

Driver license

Education

High school diploma or equivalent

Public safety certifications

Tools

Enforcement software

Handheld devices

Ticketing systems

Job description

Parking Enforcement Supervisor - Winnipeg

Application Deadline: 9 October 2026

Department: Operations - Field(OPS001)

Employment Type: Full Time

Location: I5-D40_CA-WINNIPEG-PATROL DEPT

Reporting To: Senior Operations Manager

Compensation: CA$20.72 - CA$21.78 / hour

Description

The Parking Enforcement (Patrol) Supervisor supports the Enforcement Manager in the daily operations of the parking enforcement team, ensuring compliance with parking regulations and ordinances. This role involves supervising parking enforcement officers, managing schedules in the absence of the enforcement manager, handling escalated issues, and collaborating with other departments to improve parking services. The supervisor is also responsible for training, performance evaluations, and implementing policies and procedures to enhance the efficiency and effectiveness of the parking enforcement program.

Key Responsibilities

Supervision and Leadership:

• In field operation reviews auditing, coaching, and reporting on enforcement officers' performance of KPI metrics . Minimum three (3) days per week.


• Audit team adherence to department policies and procedures.


• Identify performance issues and provide evidence to the Enforcement Manager weekly.


• Supervise enforcement officers in the absence of the Enforcement Manager.

Operations Management:

• In office operational reviews monitoring and evaluating the efficiency and effectiveness of parking enforcement operations based on ticket production, locations visited, paid/outstanding/void ticket percentage of each enforcement officer. Maximum two (2) days per week.


• Support the Enforcement Manager with developing and implementing enforcement strategies.


• Identify opportunities to improve performance in routes and utilizing data to make recommendations to the Enforcement Manager.


• Support in coordinating the maintenance and inventory of enforcement equipment and vehicles.

Data and Reporting:

• Collect and analyze data related to parking enforcement activities.


• Validate enforcement officers’ productivity against internal reports.


• Prepare reports on enforcement statistics, citation issuance, and other relevant metrics.


• Assist in the implementation of technology solutions to improve parking management.

Policy and Compliance:

• Assist in the development and revision of parking policies and procedures.

Safety and Training:

• Conduct regular training sessions on safety, enforcement techniques, and customer service.


• Ensure all staff are properly trained in the use of enforcement tools and technology.


• Review, update, and create SOPs for current and future enforcement tools.


• Promote a safe working environment and address any safety concerns promptly.

Other Responsibilities:

• Other duties as assigned by the Enforcement Manager.

Skills, Knowledge and Expertise

• High school diploma or equivalent; additional education or certifications in public safety, law enforcement, or a related field preferred.


• Minimum of 3-5 years of experience in parking enforcement, law enforcement, or public safety, with at least 1-2 years in a supervisory role.


• Strong knowledge of local parking regulations and enforcement procedures.


• Excellent leadership, communication, and interpersonal skills.


• Ability to handle difficult situations and resolve conflicts effectively.


• Proficiency in using enforcement technology, including handheld devices and software applications.


• Valid driver’s license and clean driving record.

PHYSICAL DEMANDS:

• The physical demands described here are representative of those that must be met by an employee to successfully perform the essential functions of this job.


• Ability to lift and carry equipment and supplies up to 25 pounds.


• Ability to perform duties requiring frequent standing, walking, bending, and reaching.

WORKING CONDITIONS:

• Work is performed both in an office environment and outdoors, with exposure to various weather conditions.


• May require standing and/or walking for extended periods.


• Must be available to work flexible hours, including evenings, weekends, and holidays as needed.

Benefits

• Employee Assistance Program (EAP): Confidential support for mental health, financial, legal advice, and more for everyone in your home


• Paid Vacation: Enjoy well-deserved time off to relax, travel, or spend time with family

UNION:

• If this position is union‑represented, employment terms, benefits, and conditions are governed by the applicable Collective Bargaining Agreement (CBA).