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Chief Pilot

Job in Mississauga, Ontario, Canada
Listing for: Skyservice Business Aviation
Full Time position
Listed on 2026-06-29
Job specializations:
  • Transportation
    Aerospace / Aviation / Avionics, Pilot
Job Description & How to Apply Below
JOB PURPOSE
The Chief Pilot supervises flight crew members, including pilots and flight attendants, to ensure the highest standards of safety, regulatory compliance, professionalism, and operational efficiency. This role works closely with Flight Operations and Maintenance to support the seamless execution of flight operations while upholding Company policies and Transport Canada requirements.

SUMMARY OF RESPONSIBILITIES

Develop and maintain safe and efficient standard operating procedures, ensuring that, where possible, aircraft operating procedures reflect a high degree of standardization and commonality among all aircraft types.

Confirm that flight crew members meet regulatory requirements applicable to their designated duties.

Provide leadership, supervision, coaching, and performance management to flight crew members, ensuring safe, compliant, professional, and consistent execution of assigned duties in accordance with Company policies, SOPs, the Commercial Operations Manual, and applicable regulatory requirements.

Prepare technical data concerning new routes and aerodromes, assess new routes and aerodromes for operational suitability, and provide the training required prior to their introduction.

Maintain aircraft operating manuals and Minimum Equipment Lists.

Issue directives, notices, and operations bulletins to flight crew members concerning aircraft operations.

Process, action, and follow up on mission, accident, incident, and occurrence reports.

Monitor the progress of probationary pilots and make recommendations to the Director, Flight Operations regarding their performance/retention.

Support the SMS program as required, with particular emphasis on information flow.

Ensure all pilots adhere to the Company security policy.

QUALIFICATIONS AND SKILLS REQUIRED

Hold a valid Airline Transport Pilot License, a valid Instrument Rating for an airplane subject to Canadian Aviation Regulations (CARs) Part VII, Subpart 4, and a valid medical certificate, as required.

Hold a type rating for at least one of the aircraft types operated, if applicable.

Have a minimum of three years’ experience as Pilot-in-Command of a commuter aircraft, as defined in COM Para. 1.1.2.

Previous managerial experience in a CARs 704/705 business aviation environment is highly preferred.

Be qualified under the Company training program to act as Pilot-in-Command on one of the aircraft types operated.

Demonstrate strong knowledge of the Commercial Operations Manual, SOPs, and applicable regulatory requirements.

Demonstrate knowledge to the Minister with respect to the Commercial Operations Manual, Training Manuals, Standard Operating Procedures, Company Check Pilot Manual, if applicable, and the regulations and standards necessary to carry out the duties and responsibilities of the position.

A Chief Pilot qualified under CARs, Part VII, Subpart 5, may serve as Chief Pilot for CARs, Part VII, Subpart 4 operations within the Company.

A Chief Pilot qualified under CARs, Part VII, Subpart 4 or Subpart 5, may serve as Chief Pilot for CARs, Part VII, Subpart 3 operations within the Company.

Maintain a record free of accidents, incidents, or violations.

Demonstrate strong leadership, coaching, and mentorship skills.

Demonstrate the ability to perform effectively in high-pressure operational environments.

Demonstrate excellent communication and stakeholder management skills.

Demonstrate sound judgment, professionalism, and emotional intelligence.

Demonstrate the ability to lead through change and operational complexity.

BENEFITS

Hybrid working arrangements

Competitive group health benefits coverage for you and your eligible dependants, including health, vision and dental plans

Employee assistant program

Group retirement savings plan with company matching contribution

Paid time off including sick days and personal days

Employee Referral Program

Service Awards

Skyservice is an equal opportunity employer and welcomes applications from all interested parties. If for any reason you cannot apply through our job board, please contact a member of our Human Resources team for special accommodation.

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