Supervisor, Transit On Demand Services

Town of Oakville; Oakville; On-site; CAD 70,000 - 90,000; Full time

Benefits offered by this job

OMERS pension

Health plan with life and disability

Work-life balance culture

Job summary

The Town of Oakville is seeking a Supervisor to oversee the delivery of specialized and on-demand transit services. You will supervise staff, plan schedules, and allocate resources to ensure safe, efficient operations in line with policies and regulations.

You will manage call-center delivery, respond to incidents, train staff on safety, and drive process improvements for demand growth, all while maintaining service levels and a high standard of customer care across shifts including weekends and

Qualifications

• Three-year college diploma or university degree in business administration or related field with at least 3 years transit operations experience.
• Valid CZ or BZ driver's license or ability to obtain CZ; safe driving record.
• Satisfactory criminal record and vulnerable sector screening within 30 days.

Responsibilities

• Oversee day-to-day performance of staff delivering on-demand services.
• Hire, train, motivate, schedule and evaluate staff; enforce disciplinary actions as needed.
• Respond to inquiries, accidents and complaints; manage detours and emergencies.
• Train staff on safety and use of protective equipment.
• Develop new on-demand services while maintaining knowledge of routes and regulations.
• Coordinate customer trip bookings, scheduling and dispatching for demand response.
• Forecast demand growth and assess budget and staffing impacts.
• Use technology to monitor service delivery and optimize resource deployment.
• Oversee Call Center service delivery; measure service levels and customer satisfaction.
• Review operating policies; monitor demand vs capacity; explore expansion to fixed routes.
• Conduct reviews of on-street service delivery by drivers and contracted taxi staff; ensure compliance.
• Work various shifts including weekends and holidays.

Skills

Staff supervision

Scheduling

Transit operations

Leadership

Education

College diploma / University degree in business administration

Job description

Posting Status

Open to all current Town of Oakville employees and external applicants

Job Details

Permanent Full Time (Non-Union)

Open to all current Town of Oakville employees and external applicants

Closing Date

Applications for this position must be received at by no later than 11:59 p.m. on September 9, 2026.

This job posting is for an existing vacancy and therefore will be filled accordingly.

We Offer

• A defined benefit pension plan (OMERS)
• Comprehensive health plan complemented with life and disability insurance
• A progressive work environment that promotes a work/life balance and strives to be a great place for great people to do great things

Reporting to the Manager, On Demand Services, this position is responsible for the supervision, planning and scheduling of all resources necessary to carry out activities related to specialized and on demand type services. This position is required to take appropriate action to ensure the safety and security of transit personnel, customers and assets in accordance with all policies, procedures, regulations and legislation governing the workplace and the delivery of service.

What can I expect to do in this role?

• Supervise and oversee the day-to-day job performance of all staff associated with the delivery of specialized and on demand services to ensure work is performed effectively and efficiently and in accordance with town or departmental standards, levels of service, specifications, policies, procedures and legislated requirements;
• Select, motivate, train, manage and evaluate staff, and schedule work according to priorities and review employee performance on a regular basis and take corrective/disciplinary action as required in accordance with the collective agreements and town/transit policies;
• Respond to, investigate and follow up on inquires, accidents and complaints. Initiate appropriate action in response to change offs, detours, emergencies, collisions etc.;
• Train and instruct new and existing staff to perform job functions properly and safely ensuring all staff work safely, utilizing required health and safety equipment, personal protective equipment, and protective devices as required;
• Assist the Manager in the development of new on demand services while maintaining a good working knowledge of all conventional routes, schedules and regulations;
• Provide ongoing oversight of customer trip bookings, scheduling and dispatching for demand response services including monitoring and evaluating all processes, systems and procedures to optimize service and ensure appropriate allocation of staff resources;
• Monitor and analyze demand growth rates in order to forecast future demand for service as well as budget and staffing impacts;
• Utilize technology to monitor service delivery and make recommendations for improved deployment of resources.
• Supervise the day-to-day Call Center service delivery by developing and implementing practices and mechanisms that measure and report on objectives related to service level and response time, customer satisfaction, and service quality.
• Evaluate and recommend operating policies and procedures related to the efficient delivery of on demand services. Monitor service relative to demand and capacity; identify opportunities for expansion of service and/or transition to fixed route conventional service;
• Conduct reviews, assessments and audits of on street service delivery by demand response drivers and contracted taxi staff; ensuring compliance with legislation, town and transit policies and procedures;
• Work various shifts (days, evenings, weekends and statutory holidays) covering a seven-day a week operation.

How do I qualify?

Completion of a three-year college diploma or university degree in business administration or related field, complimented by at least 3 years of related experience working in a transit operations environment. Your education is augmented by progressively responsible positions that have resulted in outstanding leadership complemented by a highly developed understanding of transit systems, municipal government and service delivery. Exposure to a call center and/or demand response type of service would be considered an asset. Candidates without the above-noted educational qualifications may be considered if they have at least 4 years' supervisory experience working in a transit operations environment.

You must also have a valid and unrestricted CZ or BZ License, or you must be capable of obtaining a CZ license as a condition of your employment and have a driving record that demonstrates responsible and safe driving behaviour. You have completed the Fleet Driver Training Course to issue C licenses and issue air brake endorsements, or you must be capable of successfully completing the course as a condition of employment.

Please note that this position requires a satisfactory criminal record and vulnerable sector screening check dated within the last 30 days as a condition of employment.

Core Knowledge Required For Success

You are an experienced leader with a comprehensive knowledge of:

• Current and future policies, practices, trends, technology and information relating to safety practices/regulations, and transit operations including scheduling, service adjustment methods, emergency operating procedures coupled with knowledge of transit regulations, town policies and procedures, collective agreement provisions and other relevant guidelines and processes that apply to Transit services.
• Occupational Health and Safety Act, Highway Traffic Act, Ontario Human Rights Code and related orders including disability accommodation and accessibility requirements pertaining to customers and employees; and Accessibility for Ontarians with Disabilities Act and directives as these apply;
• Knowledge of computer applications used to deliver transit on-demand response services, common word processing, spreadsheet, email and database management techniques.

Supervisor leadership competencies

• Strategic Thinking - innovating through analysis and ideas
• Engagement - mobilizing people, organizations, partners
• Management excellence - delivering results through action management, people management and financial and asset management
• Accountability and Respect - serving with integrity and respect

Corporate Values

Teamwork, accountability, dedication, honesty, innovation and respect

DATED: August 26, 2026

Revised August 28, 2026

The Town's recruitment software includes elements of artificial intelligence to assist in the screening and short-listing of qualified candidates.

This job profile reflects the general requirements necessary to perform the principal functions of the job. This does not include all of the work requirements of the job. Applicants are required to demonstrate through their application and in the interview process that their qualifications match those specified. Applicants may also be required to undergo testing.

We thank all applicants and advise that only those selected for an interview will be contacted.

Click to view the competencies for this Supervisor level.