Parking Enforcement Supervisor - Winnipeg

Reimagined Parking Inc.; Vancouver; On-site; CAD 29,000 - 30,000; Full time

Benefits offered by this job

Employee Assistance Program (EAP)

Paid Vacation

Job summary

Reimagined Parking Inc. is seeking a Parking Enforcement Supervisor (Winnipeg) to oversee field operations, coach staff, and implement effective enforcement policies.

You will manage scheduling, drive performance with KPI reviews, and support data-driven decisions for improved parking services. The role requires 3–5 years in parking enforcement with supervisory exposure, a valid driver’s license, and the ability to work flexible hours in an outdoor/officed setting.

Qualifications

• Requires high school diploma or equivalent; preferred public safety/law enforcement credentials.
• 3–5 years in parking enforcement or public safety with 1–2 years in a supervisory role.
• Strong knowledge of local parking regulations and enforcement procedures.

Responsibilities

• Supervise parking enforcement officers; manage schedules when the enforcement manager is absent.
• Audit KPI performance; provide coaching and reports.
• Develop and implement enforcement strategies and routes to improve performance.
• Coordinate maintenance and inventory of enforcement equipment and vehicles.

Skills

Leadership

Communication

Interpersonal skills

Enforcement technology

Public safety knowledge

Valid driver’s license

Education

High school diploma or equivalent

Public safety / law enforcement certifications

Tools

Handheld enforcement devices

Parking enforcement software

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).