Director, Passenger Transportation Services
Calgary, Alberta
Posted: July 7, 2026
Salary Range: $110,000 - $150,000 CAD annually
About the Role
A growing passenger transportation service provider is seeking an experienced Director, Passenger Transportation Services to lead operations in Calgary. This is a senior, multi-dimensional role spanning operations leadership, labour relations, people management, and project delivery. The successful candidate will be a key partner to executive leadership, particularly given the company's evolving unionized environment and an active roster of infrastructure and process improvement initiatives. The role is not limited to any single service line and may expand to include additional passenger transportation contracts as the business grows.
This role requires someone who can operate independently across three distinct disciplines: operational excellence in passenger transportation service delivery, soundlabour relations judgment, and disciplined project management execution.
Key Responsibilities
Operations Leadership
- Oversee daily passenger transportation operations, including scheduling, dispatch, on-time performance (OTP), and fleet/vehicle allocation
- Monitor and address driver performance issues, including OTP shortfalls, in a fair andconsistent manner
- Ensure equitable distribution of vehicles (including hybrid fleet) across drivers androutes
- Supervise dispatch staff, including coaching on communication tone,professionalism, and documentation standards
- Identify and close gaps in operational processes, such as end-of-shift reporting andreview procedures
Labour Relations & People Management
- Serve as a primary point of contact for labour relations matters, working closely with legal counsel on strategy, tone, and communication approach
- Interpret and apply the collective agreement; manage grievances through to resolution
- Support and help lead collective bargaining processes, including preparation,communication planning, and follow-through
- Manage discipline processes fairly and consistently, ensuring documentation meets legal and organizational standards
- Lead employee engagement initiatives that build workforce stability, recognizing thata stable, engaged workforce strengthens customer relationships and service qualitywhile lowering recruiting and training costs
- Design and drive onboarding, retention, and recognition strategies for drivers and dispatchers, with a focus on treating people fairly and consistently to prevent issues before they escalate
- Navigate matters related to union certification and representation with sound judgment, in coordination with legal counsel
Project Management
- Lead and drive to completion capital and infrastructure projects (e.g., facility/building projects) on defined timelines
- Own implementation of new systems, tools, and SOPs (including AI-enabled process improvements), from planning through rollout and adoption
- Establish clear milestones, accountability structures, and status reporting for all activeprojects
- Proactively surface risks, delays, and resourcing needs to leadership rather than allowing projects to stall
Business Development & Growth
- Identify and lead initiatives to grow and strengthen the business, including new service opportunities, contract expansion, and operational efficiencies that support growth
- Bring forward proposals and business cases for growth initiatives, not just execute ondirection from above
Training
- Own the training function for drivers, dispatchers, and operational staff —onboarding, ongoing skills development, and compliance training
- Build and maintain training materials and programs that support consistent service quality and reduce early-tenure attrition
Customer Service & Stakeholder Relationships
- Build and maintain strong, trust-based relationships with Calgary Transit Access and other key external stakeholders
- Champion service excellence and customer service standards across the operation
- Act as a primary relationship owner for external partners, representing the company professionally and proactively
Succession & Continuity
- Document processes, decisions, and institutional knowledge to support organizational continuity
- Build capacity within the operations team so that routine functions can be delegated appropriately
Ownership & Independent Execution
- Operate independently and take full ownership of the role, with minimal direct supervision — thinking and acting like a business owner rather than waiting for direction
- Take initiative in identifying problems and driving improvements across all areas ofthe operation
- Track and measure all operational KPIs on an ongoing basis, with a mandatory expectation of meeting and exceeding baseline KPI targets, not simply maintaining them
- Prepare strong, clear, and useful executive management reports on a regular basis tokeep leadership informed without requiring leadership to chase for updates
- Prepare and present presentations to executive leadership and external stakeholders as required
Qualifications
Required
- 5+ years of senior management experience within passenger transportation, paratransit, public transit, on-demand transit, or a closely related service
- Demonstrated experience in labour relations, ideally within a unionized or newly-unionizing environment (collective agreement interpretation, grievance handling,bargaining support)
- Proven project management experience, with a track record of taking projects from planning to completion on schedule
- Strong people management skills, including performance management, coaching, and discipline
- Excellent judgment and discretion in handling sensitive HR and labour matters
- A collaborative, fair, and consistent approach to working with unions — someone who understands the give-and-take of the relationship rather than treating every issue as abattle, while still being firm enough to protect the company's interests
- Strong written and verbal communication skills, adaptable across formal (email, legal correspondence) and informal (text/WhatsApp) channels
- Demonstrated ability to track, measure, and drive performance against KPIs, with a results-oriented mindset focused on exceeding targets rather than simply meeting them
- Confident presenting to executive leadership and external stakeholders, with strong presentation development and delivery skills
Preferred
- Post-secondary education in Human Resources Management, Business Administration/Management, or a related field
- Experience working directly with legal counsel on labour relations strategy
- Familiarity with ATU or similar transit union structures
- Experience with SOP development and AI/technology-enabled process improvement initiatives
- Experience managing external stakeholder relationships, ideally with municipal transit authorities (e.g., Calgary Transit Access)
- Track record of identifying and leading business growth initiatives
What We're Looking For
Above all, we're looking for someone who takes ownership — someone who volunteers information and action rather than waiting to be prompted, follows through on commitments without requiring repeated check-ins, and treats operations, labour relations, business development, and stakeholder management as core to the role rather than as competing priorities. This person should be comfortable operating with a high degree of autonomy, exercising the judgment and initiative of someone who runs the operation as if it were their own business, and communicating upward through clear, regular executive reporting rather than needing to be asked for status updates.
Reporting Structure
Reports to executive leadership. Works closely with legal counsel on labour relations matters and coordinates across operations, dispatch, and driver teams.
This is a hands-on director position. While the title reflects the seniority and scope of the role, the successful candidate will be directly involved in day-to-day operational execution rather than solely overseeing a full management layer of subordinate managers and supervisors. Candidates should be comfortable and confident operating at both strategic and hands-on levels.
We are an equal opportunity employer.
Pay: $110,000.00-$150,000.00 per year
Work Location: In person
