Build & Lead a Critical Transportation Operation
Most operations roles ask you to maintain systems.
This one asks you to build, optimize, and lead one that directly impacts people’s lives.
Care Accessible Transportation (CAT) has been delivering essential paratransit transportation services for over 30 years, with established operations in Ontario and Alberta. In Winnipeg, we operate under contract with Winnipeg Transit Plus — providing transportation for individuals who depend on it not as a convenience, but as a necessity.
We are expanding our Winnipeg operations and hiring an Operations Manager to take full ownership of our fastest-growing service. You will inherit a functioning operation and be accountable for professionalizing it, scaling it, and building the culture that sustains it.
This is not a maintenance role.
This is a build, optimize, and lead role.
What You’ll Be Responsible For:
Operations & Performance
- Oversee service delivery from 6:00 AM – Midnight across all active routes
- Manage scheduling, dispatch, and driver coverage
- Ensure strong KPI performance (on-time service, trip completion, complaints)
- Set up operational processes and standards for our newest ProMaster van service
Team Leadership & Culture
- Hire, train, and develop drivers and operations staff
- Build a culture of accountability, professionalism and respect
- Manage performance, coaching, and discipline with consistency and documentation
- Coordinate and deliver mandatory training, including wheelchair securement and passenger assistance
Contract & Stakeholder Management
- Ensure full compliance with Winnipeg Transit Plus policies, procedures, and service standards
- Act as the primary operational contact
- Prepare and present management reports for Winnipeg Transit Plus stakeholders
- Respond to customer complaints thoroughly and within contract-required timelines
Fleet & Safety
- Oversee vehicle readiness, inspections, and maintenance coordination
- Liaise with maintenance providers; manage a future in-house mechanic as the team grows
- Ensure all safety and accessibility standards are met continuously
Systems, Efficiency & Automation
- Identify system gaps across operations and reporting
- Implement technology solutions and task automation to eliminate repetitive work and improve accuracy
- Build scalable processes that reduce manual effort and improve efficiency
Financial Oversight
- Manage operational budgets and track expenditures, identifying variances and reporting to leadership
- Review payroll inputs for accuracy for both employed drivers and contractors
- Contribute financial summaries and cost analysis to management reports
What We’re Looking For
This role is for someone who:
- Takes ownership without being asked
- Sees system gaps and immediately thinks, “I can fix this”
- Actively looks for ways to improve efficiency through technology and task automation
- Is comfortable managing people, systems, and real-time operations simultaneously
- Understands that leadership = accountability
Requirements
- 5+ years of operations, logistics, or transportation leadership experience
- Experience managing diverse teams in fast-paced or real-time environments
- Experience managing HR processes, including hiring, performance management, and payroll review
- Strong problem-solving and decision-making skills
- Comfortable using technology and data to improve operations
- Excellent written and verbal communication skills
- Criminal record check with Vulnerable Sector Search required prior to start
- Legally authorized to work in Canada
Assets (Not Required)
- Experience in paratransit, accessible transit, or government-contracted transportation
- Familiarity with SpareLabs or comparable dispatch and scheduling platforms
- Manitoba Class 4 driver’s licence or equivalent
- Knowledge of the Accessibility for Manitobans Act or Winnipeg Transit Plus standards
- Background in a multi-location or growth-stage service operation
Who This Role Is NOT For
This role is not a fit if you:
- Prefer highly structured, slow-moving environments
- Avoid difficult conversations or accountability
- Need constant direction to move forward
Why Join Care Accessible Transportation
Established Since 1994
30+ years of operations in Ontario and Alberta — now growing in Winnipeg.
Long-Term Team Stability
Many team members stay 5–10+ years. We build careers, not just jobs.
Purpose-Driven Work
The people we serve rely on this service. Your work has real, daily impact.
Room to Build
Shape a growing operation and leave your mark on how it runs.
Compensation & Schedule
Salary
$70,000 – $90,000, commensurate with experience
Incentives
Performance-based incentives tied to service quality and contract outcomes
Type
Full-Time, Permanent
Location
On-Site, Winnipeg, MB
Schedule
Operational hours 6:00 AM – Midnight; flexibility required for early mornings, evenings, or urgent operational needs
Benefits
Extended health and dental (after probationary period); paid vacation and statutory holidays per Manitoba Employment Standards
Apply Now
If you’re looking for a role where you build systems, improve operations through technology, and your work directly impacts people’s lives — apply today.
Submit your application with:
- Your current resume (PDF preferred)
- A brief cover letter (3–5 sentences): your operations experience, the size of team you managed, and what draws you to accessible transportation
Shortlisted candidates will be contacted within 5 business days. A driver’s abstract will be requested at the pre-selection stage.
We are actively recruiting and will close this posting once the position is filled.
Pay: $70,000.00-$90,000.00 per year
Benefits:
- Dental care
- Extended health care
- Paid time off
Application question(s):
- Describe one operational improvement or system you implemented that improved efficiency. What was the result?
Experience:
- Operations management: 5 years (preferred)
Work Location: In person
