Vice President, Flight Operations

Take Your Career to New Heights with Flair Airlines

We’re here to make air travel affordable for everyone, and we’re looking for talented individuals who want to help us continue changing the industry for the better. As Canada’s most reliable airline, we're all about offering real value. As we continue to expand our network, increase flight frequencies, and introduce more services, we’re looking for passionate team members to help us in our mission to make air travel accessible for everyone. We know who we are, and we’re confident in our approach.

Your Team:

Join Flair’s Flight Operations team, where executive leadership and operational oversight support the safe, reliable, and efficient operation of the airline. Reporting to the Chief Operating Officer (COO), the Vice President, Flight Operations is responsible for the strategic direction and performance of Flight Operations, the Chief Pilot’s Office, Pilot Training, Crew Resources and Planning, Dispatch, and the Operational Control Centre (OCC). The role ensures operational priorities, resources, and capabilities are aligned with regulatory requirements, business objectives, and long-term growth plans.

The Vice President, Flight Operations, supports the COO, who holds the Operations Manager designation under the Canadian Aviation Regulations (CARs), in fulfilling the associated regulatory and operational responsibilities. The role provides executive oversight of operational performance, crew planning, training, safety, and risk management while driving improvements in reliability and efficiency across the network.

Working with the Executive Leadership Team, the Vice President supports fleet growth, new base openings, and extended-range operations by ensuring workforce planning, training capacity, operational systems, and technology investments are aligned with the airline’s evolving needs.

This role is based on-site at our Toronto, ON (YYZ) office.

A Day in the Life:

Executive Leadership and Strategy

• Provide executive leadership for the safe, compliant, and efficient operation of Flair's Flight Operations portfolio, including Flight Operations, the Chief Pilot's Office, Pilot Training, Crew Resources and Planning, and the OCC.
• Lead the development and execution of the Flight Operations strategy in alignment with Flair's broader operational priorities, flairFWD pillars, and business objectives.
• Own Flight Operations' operating budget, including crew, training, and OCC/dispatch costs, and manage resource allocation in line with the Company's operating plan and capital priorities.
• Lead the Flight Operations leadership team, ensuring the appropriate structure, resources, and capabilities are in place to support safe and effective operations across all areas of responsibility.

Regulatory Compliance and Support to the Operations Manager

• Support the Chief Operating Officer, who holds the Operations Manager designation under the CARs, in the control of operations and operational standards for all aircraft operated, and in the identification of operations coordination functions that affect operational control, such as maintenance, crew scheduling, load control, and equipment scheduling.
• Ensure crew scheduling and Dispatch operations comply with flight and duty time regulations, and that Flight Crew Members are kept informed of changes to applicable regulations and standards.
• Oversee the receipt and actioning of aeronautical information affecting the safety of flight, and support the dissemination of aircraft safety information, both internal and external, in conjunction with Flair's SMS.
• Maintain a current Operations electronic Master Library, and support the Operations Manager in the governance, content, and amendment of the Company Operations Manual (COM) and other Flight Operations documentation.
• Act as Flight Operations' day-to-day point of contact with Transport Canada and other regulatory authorities on matters related to Flight Operations, including compliance, audits, approvals, and Air Operator Certificate (AOC) matters, in coordination with the Operations Manager.

Safety Management System (SMS) Oversight

• Provide executive oversight of the SMS within the Flight Operations function, including hazard reporting, risk management, corrective action follow-up, and safety performance monitoring, exercising the responsibilities described in Flair's SMS Policy Manual.
• Lead the identification, assessment, and management of operational risks across the Flight Operations portfolio, ensuring appropriate mitigation strategies and escalation protocols are in place.
• Support the Chief Pilot's Office on the Flight Data Monitoring (FDM) program and other flight-data-driven safety initiatives, consistent with Flair's SMS governance model.

Crew Resources, Training, and Labour Relations

• Maintain accountability for pilot qualifications, operational training standards, and the continued readiness of Flight Crew Members in accordance with regulatory and Company requirements.
• Own pilot workforce planning and crew resource strategy, including hiring, training capacity, and crew base planning, in partnership with the Director, Crew Resources, to support network growth and fleet changes.
• Serve as the senior Flight Operations executive on labour relations matters affecting Flight Crew Members, partnering with the Chief of People and external legal counsel on administration of the pilot collective agreement, including grievance response and collective agreement obligations tied to network and base changes.
• Oversee crew scheduling and rostering technology and related processes, ensuring compliance with flight and duty time regulations and the applicable collective agreement.

Network Growth, Certification Programs, and Continuous Improvement

• Support Flair's fleet growth and network expansion, including new base openings and extended-range operations, by ensuring Flight Operations crew, training, and OCC/dispatch capacity are in place ahead of go-live.
• Partner with the Vice President, Maintenance on Flair's ETOPS/EDTO certification program, ensuring flight operations procedures, crew training, and dispatch/OCC readiness support the targeted Transport Canada approval.
• Support Flair's IOSA certification preparation for Flight Operations-related standards, partnering with the Director, Safety, Security & Compliance on Flight Operations Safety Performance Indicators (SPIs).
• Lead continuous improvement initiatives that enhance operational performance, regulatory compliance, crew readiness, and long-term operational capability, including Flight Operations technology such as electronic flight bags (EFB), the crew app, and crew scheduling systems.

Governance and Stakeholder Reporting

• Ensure effective coordination across operational control functions that affect the safety and efficiency of the airline, including Maintenance, crew scheduling, dispatch, and other operational support teams.
• Provide timely and transparent updates to the Chief Operating Officer, the President & CEO, and the Executive Leadership Team on operational performance, material risks, and issues affecting the operation.
• Support enterprise-level planning and decision-making by contributing operational insight, risk analysis, and performance recommendations.
• Foster strong cross-functional alignment with operational and corporate departments to ensure Flight Operations priorities support broader Company objectives.
• Perform other duties as delegated by the Chief Operating Officer or the President & CEO.

What You Bring to the Role:

The preferred candidate should exemplify Flair's core values: honesty, efficiency, accountability, and respect, while demonstrating success in previous roles. Additionally, we are seeking individuals who possess:

• Education:
  • Bachelor's degree in Civil Aviation, Aviation Management, Business, or a related field is required; an equivalent combination of advanced operational experience, training, and education will be considered.
  • A commercial pilot background is required.
• Experience:
  • Minimum of 10 years of progressive leadership experience in commercial aviation operations, including substantial senior management or executive-level responsibility.
  • Extensive experience directing Flight Operations within a Transport Canada-regulated CAR 705 airline environment.
  • Comprehensive operational leadership experience across Flight Operations, pilot training, crew planning, operational control, regulatory compliance, and aviation safety.
  • Experience managing a unionized pilot workforce, including collective agreement administration, labour relations, and working with ALPA or an equivalent union.
  • Demonstrated ability to lead large, multidisciplinary teams with accountability for operational performance, safety, regulatory compliance, and resource management.
  • Executive-level experience contributing to business strategy, operational planning, financial decisions, and long-term organizational priorities.
  • Track record of leading operational improvements, managing complex organizational changes, and addressing operational and regulatory risks.
  • Direct experience engaging with Transport Canada and other aviation regulatory authorities on certification, operational approvals, regulatory compliance, and certificate management.
  • Experience with ETOPS/EDTO certification or other significant operational approval programs is considered an asset.
  • Familiarity with modern crew scheduling, crew bidding, and operational planning systems is preferred.
• Core Competencies:
  • Strategic leadership and business judgment, with the ability to align Flight Operations priorities with organizational objectives, financial performance, and long-term growth.
  • Advanced knowledge of Canadian Aviation Regulations (CARs), Transport Canada requirements, and regulatory obligations governing commercial airline operations.
  • Ability to provide executive oversight of complex flight operations while maintaining high standards of safety, regulatory compliance, operational reliability, and performance.
  • Sound decision-making and risk management capabilities, particularly when addressing operational disruptions, safety concerns, and time-sensitive business decisions.
  • Effective leadership, coaching, and succession planning capabilities, with the ability to develop senior leaders and strengthen accountability across operational teams.
  • Ability to navigate complex labour relations matters, interpret collective agreements, and maintain productive relationships with union representatives and pilot groups.
  • Financial and commercial acumen, including operational budgeting, resource allocation, cost management, and evaluation of capital investments.
  • Ability to assess operational capacity, workforce requirements, training resources, and system capabilities to support fleet expansion and business growth.
  • Excellent communication, negotiation, and stakeholder management skills, with the ability to engage effectively with executive leadership, regulatory authorities, union representatives, and operational teams.
  • Strong analytical and problem-solving capabilities, with the ability to interpret operational performance data, identify emerging risks, and implement sustainable improvements.
  • Ability to lead organizational change, establish clear priorities, and drive cross-functional initiatives while maintaining operational continuity.
• Requirements:
  • Clear criminal record check and satisfactory references. 
  • Must be able to obtain and maintain a valid Restricted Area Identity Card (RAIC).
  • Must be legally eligible to work in Canada without restriction.

Why You’ll Love Working Here:

At Flair, we prioritize our teams by cultivating a supportive, collaborative work environment filled with opportunities for growth. Investing in our people is at the heart of what we do because your success fuels our collective achievements. We are dedicated to fostering a workplace where leaders thrive, innovation flourishes, and every team member feels valued and empowered.

From the moment you join us, you’ll have access to a comprehensive benefits package designed to support your well-being - because when you’re at your best, so are we. This benefits package includes:

• Comprehensive Salary– A salary that reflects your experience and contributions.
• Comprehensive Benefits – Competitive medical and dental coverage, disability insurance, life insurance, and an employee & family assistance program.
• Retirement Savings – A pension plan with employer-matched contributions.
• Unlimited Travel Perks – Enjoy free and discounted flights for you and your travel companions.

If you’re ready to join a team that’s bold, innovative, and fun, we want to hear from you!

Your Career, Your Journey - Join Flair!

If you’re ready to embark on this exciting journey with Flair Airlines, please submit your resume through the job posting and answer a few questions about your experience and suitability for the role. We look forward to reviewing your application.

Apply by: October 30, 2026

At Flair, we’re committed to building an inclusive, equal, and accessible workplace that welcomes diverse talent. We encourage candidates from all backgrounds to apply. If you need accommodation during the selection process, just let us know.

We thank all applicants for their interest in Flair; however, only those selected to continue in the process will be contacted.

Website: flyflair.com