Chief Pilot – Flight Operations Leader

Pilot Assessments; Montreal (administrative region); On-site; CAD 120,000 - 180,000; Full time

Job summary

Pilot Assessments is seeking an experienced Chief Pilot to provide strategic and hands-on leadership. You will oversee day-to-day flight operations, guiding flight crews and ensuring safe transportation in line with aviation regulations and company standards.

You will lead offshore fleet operations, promote safety culture, and collaborate with stakeholders to align scheduling, training, and readiness. This role demands strong leadership, decision-making, and clear communication under pressure.

Qualifications

• Demonstrated leadership in flight operations and safety excellence.
• Strong knowledge of aviation regulations and compliant dispatch.
• Proven ability to lead diverse flight crews and inspire high standards.

Responsibilities

• Lead flight operations to meet ACASS’s goals and service commitments.
• Ensure aircraft are dispatched with safety as the top priority.
• Maintain compliance with aviation regulations, company policies, and procedures.
• Oversee offshore fleet operations with consistent professional standards.
• Coach and mentor flight crews to achieve exceptional performance.
• Foster a safety culture and continuous improvement mindset.
• Collaborate with stakeholders to align scheduling, training, and readiness.

Skills

Flight ops leadership

Regulatory compliance

People leadership

Decision making under pressure

Stakeholder communication

Job description

About the role

As Chief Pilot, you provide strategic and hands‑on leadership to meet ACASS’s operational goals. You’ll oversee day‑to‑day flight operations, guiding flight crews and ensuring the safe transportation of our customers and passengers in alignment with applicable aviation regulations and company policies, standards, and procedures.

What you’ll do

• Lead flight operations to meet and exceed ACASS’s operational goals and service commitments.
• Ensure all aircraft are dispatched with passenger and crew safety as the top priority.
• Maintain strict compliance with applicable aviation regulations and company policies, standards, and procedures.
• Oversee the offshore fleet, upholding consistent professional standards across all operations.
• Coach, mentor, and support flight crew to achieve exceptional performance and professionalism.
• Promote a robust safety culture and continuous improvement mindset across the operation.
• Collaborate with internal stakeholders to align scheduling, training, and operational readiness.

What you bring

• Proven leadership experience in flight operations with a track record of elevating safety and operational excellence.
• Thorough understanding of applicable aviation regulations and best practices for compliant dispatch and operations.
• Strong people leadership skills with the ability to inspire, guide, and uphold professional standards across diverse crews.
• Sound judgment, decisive problem‑solving, and a calm, safety‑focused approach under pressure.
• Clear, confident communication and stakeholder management skills.

Note: Specific license or flight‑hour requirements were not provided in the employer’s listing.

Why you’ll love this role

• High‑impact leadership role shaping safety, standards, and operational outcomes.
• Global exposure through oversight of an offshore fleet.
• Collaborative culture focused on professionalism, integrity, and continuous improvement.

Location & schedule

Base: Montreal, Quebec, Canada

Status: Permanent, full‑time

You’ll be based in Montreal with leadership oversight of an offshore fleet and flight crews.