Job Summary
We are seeking a highly experienced and motivated individual for the Chief Pilot – Rotary Wing position to lead and manage helicopter flight operations based in Winnipeg, MB.
This position is intended for a senior pilot with strong administrative and leadership experience and may be structured as administrative-only or administrative with flying duties, depending on operational requirements and candidate qualifications.
The Chief Pilot will provide strategic and operational oversight of flight operations, ensure regulatory compliance, and support day and night operations, including NVG operations where applicable.
Key Responsibilities
Operational & Regulatory Oversight
- Act as the company’s Chief Pilot in accordance with Transport Canada regulations
- Ensure compliance with the Company Operations Manual (COM), SOPs, and CARs
- Provide oversight of pilot training, checking, standardization, and operational proficiency
- Support operational readiness for Day and Night VFR operations
Leadership & Administration
- Lead, mentor, and manage flight crews
- Maintain complete and accurate personnel files for all flight crew members
- Coordinate all pilot training as required by the COM
- Coordinate specialized operational training programs as needed
- Manage pilot development and career progression
- Manage pilot assignments based on skill sets, experience, and training
- Participate in pilot recruitment, selection, and performance management
- Oversee scheduling, operational planning, and flight/duty time compliance
- Support the Safety Management System (SMS), risk assessments, and occurrence reporting
- Carry out Risk Assessments and develop SOP’s where appropriate
- Contribute to operational planning, budgeting, and continuous improvement initiatives.
Flying Duties (if applicable)
- Conduct line flying and operational missions as required
- Maintain currency and proficiency for aircraft type, night, and NVG qualifications
- Provide operational support during peak or specialized missions
Minimum Qualifications
- Minimum 3,000 hours total rotary-wing flight time
- Minimum 250 hours night flight time
- Night rating (mandatory)
- Strong experience on Bell 206 series (mandatory)
- Valid Canadian ATPL-H or CPL-H
- Proven administrative and senior leadership experience in an aviation environment
- Strong working knowledge of Canadian Aviation Regulations (CARs)
- Excellent communication, organizational, and decision-making skills
- Legally entitled to work in Canada
Preferred Qualifications
- IFR rating
- Dual-rated (helicopter and fixed-wing) preferred
- Bell 407 series or similar
- NVG training and operational experience
- Previous Chief Pilot or senior flight operations management experience
- Experience in multi-crew, complex, or mixed-fleet environments
- Familiarity with Transport Canada oversight, audits, and SMS implementation
- Experience supporting government or commercial aviation programs
Job Type: Full-time
Pay: $135,000.00-$190,000.00 per year
Benefits:
- Dental care
- Extended health care
- Paid time off
Application question(s):
- Do you have a Commercial Rotary Wing License with a minimum of 2500 hours PIC
Experience:
- Industry : 8 years (required)
Work Location: In person
