Job Description

If you're an experienced and dedicated professional passionate about road safety, we invite you to apply for the

Crossing Safety Supervisor

position. Join us in helping create safer and more efficient roadways for our community.

Duties & Responsibilities

Oversee day-to-day operations of all crosswalk intersections in the assigned region Recruit, train, and manage a team of 90-130 school crossing guards across 60-100 locations Develop and maintain staff schedules, ensuring full coverage Monitor intersection performance and implement improvements as needed Ensure compliance with safety regulations and company policies Collaborate with the Operations Team and report directly to the Director of Operations

Working Conditions

Monday to Friday operations, with flexibility required for urgent matters or after-hours needs Supervises between 60-100 crossing guard locations (subject to change based on company needs) Frequent travel between assigned locations within Scarborough and East York; personal vehicle required Outdoor work in all weather conditions to perform quality assurance checks, staff evaluations, or occasional coverage when standbys are unavailable Regular communication with school principals, guards, and the operations team Periods of desk work for scheduling, reporting, and administrative duties Must be comfortable balancing field supervision with office-based coordination and reporting

Qualifications

Strong communication and leadership skills Previous managerial experience required Able to make sound decisions in high-pressure situations Technology proficient (scheduling software, CRM, Excel, PowerPoint, smartphones) Excellent problem-solving and customer service abilities Resourceful, reliable, and able to motivate staff HR, business, or supervisory experience preferred

How to Apply:

Please send your resume to

andrea@carraway.ca

by November 21, 2025. You must have your own vehicle, reside in Toronto and must be over the age of 26.

We thank all applicants for their interest; only those selected will be contacted.

Job Type: Full-time

Pay: $52,000.00 per year

Benefits:

Dental care Extended health care Mileage reimbursement Paid time off Vision care
Work Location: In person