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Assistant Chief Pilot – Flight Operations

Job in Winnipeg, Manitoba, A3C, Canada
Listing for: Pilot Assessments
Full Time position
Listed on 2026-10-17
Job specializations:
  • Transportation
    Pilot, Aerospace / Aviation / Avionics
Salary/Wage Range or Industry Benchmark: 120000 - 180000 CAD Yearly CAD 120000.00 180000.00 YEAR
Job Description & How to Apply Below
Position: Assistant Chief Pilot – Flight Operations )

Lead from the flight deck and the front office. Perimeter Aviation is seeking an Assistant Chief Pilot to help drive safe, on-time, and compliant operations while remaining current on the line. This leadership role blends operational oversight, pilot coaching, training coordination, and Safety Management System stewardship—with a requirement to fly a minimum of two scheduled days per month (or as operationally required).

  • Company:
    Perimeter Aviation
  • Location:

    Winnipeg, Manitoba, Canada
  • Aircraft Types:
    Metro, Merlin, Dash 8
  • Operations:
    Scheduled passenger and freight, charter, medical evacuation, and other company services across 703/704/705
  • Reports To:

    Chief Pilot
  • Minimum Line Flying: 2 scheduled days/month (or as required)
  • License required:  (Aeroplanes) with valid Group 1 Instrument Rating
  • Supervise flight crew to ensure safe, effective, and punctual operations in full compliance with company procedures and regulatory standards.
  • Manage delegated line-operations tasks and pilot group oversight, fostering engagement, professionalism, and customer satisfaction.
  • Administer and champion the Safety Management System (SMS), including coordination of SMS activities and support for emergency response.
  • Coordinate aircraft, simulator, and ground training; conduct or delegate line checks; and carry out ACP duties as required.
  • Issue and administer operational directives and notices to flight crew to maintain standardization.
  • Collaborate with third-party providers for 703/704/705 operations, including performance data, charter coordination, Nav Canada, and airport authorities.
  • Fly the line at least two scheduled days per month (or as operationally required) to stay current and connected to day-to-day operations.
  • Step in for departmental coverage as needed and complete additional duties assigned by the Chief Pilot.
  • High school diploma or GED equivalent.
  • Valid ATPL (Aeroplanes) with a valid Group 1 Instrument Rating.
  • Type rating on at least one company aircraft type (Metro, Merlin, or Dash
    8) and qualification as PIC under the company training program on one operated type.
  • Minimum three years’ experience as Pilot-in-Command on company aircraft.
  • Proven knowledge of the Company Operations Manual, Flight Crew Training Manual, SOPs, Company Check Pilot Manual, and applicable regulations/standards.
  • Proficiency with Microsoft Outlook, Excel, and Word.
  • Ability to obtain and maintain required transportation security clearances and other authorizations.
  • Strong communication skills with the ability to conduct presentations and coach pilot groups.
  • Willingness to travel by aircraft and other means; availability for varied shifts in a fast-paced airline environment.
  • Physical ability to perform the role, including lifting and carrying up to 50 pounds.
  • Asset:
    Indigenous and Cultural Awareness Training.
  • Lead with impact across diverse operations—scheduled passenger, freight, charter, and medevac—serving communities throughout the region.
  • Balance strategic leadership with active flying to keep your skills sharp and your decision-making grounded in real-world operations.
  • Play a key role in safety, standardization, and performance excellence within a collaborative, mission-driven flight operations team.
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