Chief Pilot - Winnipeg, MB

Position Title:    Chief Pilot
Location:            Winnipeg, MB
Status:                Full Time
Start Date:         Immediately

Position Summary:

Reporting to the Director of Flight Operations, the Chief Pilot is responsible for leading, mentoring and coaching all line pilots including the Assistant Chief Pilot. They manage and develop all standard operating procedures in accordance with Transport Canada regulations and ensure ongoing compliance with the pilot collective bargaining agreement. 

Primary Duties & Responsibilities:


  • Developing standard operating procedures
  • Implement all required approved training programs for the air operator flight crews
  • Issuing directives and notices to the flight crews as required
  • Determining the operational suitability and requirements of all aerodromes and routes served by the air operator
  • Distribute and action all accident, incident, and other occurrence reports relative to your area
  • Process and action all flight crew reports
  • Supervision and mentorship of flight crews
  • Assuming any responsibilities delegated by the Director of Flight Operations and VP of Flight Operations
  • Delegate all responsibilities for operational duties to another qualified Pilot when unavailable
  • Responsible to maintain all pilot related administration and maintenance of records 
  • Other duties as assigned


  • Prepare (assist) with annual department budget
  • Monitor and analyze monthly expenditures to assigned GL accounts and explain variances from budget (e.g., uniform supply approvals, purchasing office supplies for training manuals, training sessions/catering and third-party approvals, simulator leasing, training travel costs for pilots, aircraft training costs)
  • Monthly Management reporting – weekly operating report
  • Monitor overtime bi-weekly and report on reasons for overtime
  • Adhere to all financial internal controls
  • Monitor department manpower to ensure within budget and seek approval for replacement/increase
  • Engage in ongoing cost reduction analysis within the Flight Operations department 

Safety & Leadership:

  • Change management leader - execute change while supporting employees through communication, listening and auctioning
  • Guide and mentor, the new and existing pilot group
  • Participate in the recruitment and selection of team members
  • Promote occupational health and safety within the department, and participate in the development and monitoring of safety training
  • Proactively communicate hazards and SMS initiatives with the department
  • Embark on employment equity initiatives
  • Engaging with all employees to promote employment equity and encouraging employees to undertake the self-declaration survey updating as necessary
  • All levels of the organization share responsibility for human rights within the organization
  • Overseeing and promoting continuous improvement on human rights and employment equity initiatives

Managers, Supervisors and Leads – have been delegated the authority and are responsible to the Department Head to actively identify hazards and deficiencies and report through the SMS (Safety Management System) Program reporting system.  Communicate with all personnel within their respective department and other departments as required to maintain effective day to day activities.  Ensure regulatory and company standards are maintained.  Assist in the development and maintenance of company processes and procedures. (Quality Assurance activities)

Carry out their duties safely within regulatory and company standards, policies, processes, and procedures as trained.  Use safety equipment (tools, Proper Protective Equipment etc.) as provided.  Actively identify and report hazards and deficiencies (when in doubt report). Assist in development of company processes and procedures as required.

Hours of Work:

Shift work is required and may include mornings/afternoons, evenings, and weekends

Qualifications & Skills:

  • ATPL License with previous 705 airline experience
  • Minimum 3 years’ experience as a pilot-in-command in a 705 operation
  • Proven ability to maintain document control
  • Strong operational knowledge
  • Post-secondary education in related field considered an asset
  • Previous supervisory/management experience an asset
  • Superior interpersonal, listening, and problem-solving skills
  • Ability to work under pressure with tight deadlines
  • Utmost integrity, discretion, confidentiality, and professionalism
  • Ability to build relationships and trust at all levels and in all functions across the organization
  • Proficient with MS Office
  • Excellent communication skills
  • Ability to maintain effective working relationships with all levels in the Company
  • Must be able to obtain and maintain a Restricted Area Pass (enhanced security clearance)
  • Inuktitut language considered an asset
  • Preference given to Inuit Land Claims Beneficiaries

If this sounds like the job for you, contact us! Calm Air International is an equal opportunity employer. We encourage interested applicants to submit a resume in confidence by December 2, 2022, to Rob Astwood at

We thank all those who apply, but only those selected for an interview will be contacted.