Executive Assistant

Flair Airlines; Toronto; On-site; CAD 60,000 - 80,000; Full time

Job summary

A Canadian airline is seeking an experienced Executive Assistant to provide high-level administrative and strategic support to the CEO. The role involves managing complex schedules, preparing reports, and coordinating executive communications. Ideal candidates will have five years of relevant experience, strong organizational skills, and proficiency in Microsoft Office. This role is based in Toronto and offers competitive benefits, including unlimited travel perks and comprehensive coverage. Apply by February 27, 2026.

Benefits

Comprehensive salary

Medical and dental coverage

Retirement savings with employer matching

Unlimited travel perks

Qualifications

• Minimum of five years of experience as an Executive Assistant or similar role.
• Experience in a regulated industry, preferably aviation.
• Proven ability to support C-suite executives effectively.

Responsibilities

• Provide high-level administrative support to the CEO.
• Manage the CEO's calendar and travel logistics.
• Assist with documentation related to regulatory compliance.

Skills

Organizational skills

Time management

Problem-solving skills

Written and verbal communication skills

Attention to detail

Education

Post-secondary education in Business Administration or related field

Tools

Microsoft Office

Microsoft Teams

SharePoint

Job description

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—but we don’t take ourselves too seriously.

Your Team

Join Flair’s Executive Office. Reporting to the Chief Executive Officer (CEO), the Executive Assistant provides senior‑level administrative and strategic support to ensure the effective day‑to‑day operation of the Executive Office. This role is responsible for managing complex schedules, travel logistics, executive communications, and meeting coordination in support of organizational priorities.

The Executive Assistant supports governance, regulatory, and compliance activities within a regulated aviation environment, including coordination of documentation and materials related to Transport Canada, the Safety Management System (SMS), audits, inspections, and regulatory reviews. The role works closely with the Executive Leadership Team and internal stakeholders to coordinate executive meetings, leadership off‑sites, and strategic planning sessions, track action items, and support follow‑up on executive decisions. Strong organizational skills, sound judgment, and a high level of discretion are required.

This role is based on‑site at our Toronto (YYZ) office.

A Day In The Life

• Provide high‑level administrative and strategic support to the CEO, ensuring seamless day‑to‑day operations of the executive office.
• Manage the CEO’s calendar, travel logistics, and meeting schedules, including coordination across time zones and remote locations.
• Assist the CEO with documentation, reporting, and correspondence related to Transport Canada, safety management systems (SMS), and regulatory compliance.
• Support preparation for audits, inspections, and regulatory reviews by coordinating materials and timelines.
• Prepare briefing materials, presentations, reports, and correspondence for internal and external stakeholders.
• Prepare and manage expense claims for the CEO.
• Coordinate executive meetings, leadership off‑sites, and strategic planning sessions, including agenda development and minutes.
• Foster strong work relationships across departments to facilitate information flow and collaboration.
• Track action items from executive meetings and ensure follow‑up with accountable stakeholders.
• Prepare project status updates, dashboards, and summaries for the executive and leadership review.
• Assist with change management initiatives, process improvements, and organizational projects.
• Maintain a high level of confidentiality when dealing with Executive Office communications and documents.
• Provide professional support to other members of the Executive Leadership Team as required.
• Perform other duties and responsibilities as assigned.

What You Bring To The Role

• Education:
  • Post‑secondary education in Business Administration, Aviation Management, Project Management, or a related field is preferred.
• Experience:
  • Minimum of five (5) years of progressive experience as an Executive Assistant, Senior Administrative Professional, or in a similar role supporting C‑suite or senior executives.
  • Demonstrated experience supporting a CEO or senior executive in a fast‑paced, high‑accountability environment.
  • Experience working in a regulated industry such as aviation, transportation, infrastructure, or government is a strong asset.
  • Experience supporting executive governance activities, including board, regulatory, or audit‑related documentation, is preferred.
  • Experience coordinating complex schedules, executive travel, and cross‑functional priorities across multiple stakeholders.
  • Experience coordinating cross‑functional projects, tracking milestones, and following up on deliverables with multiple stakeholders.
  • Advanced proficiency in Microsoft Office and collaboration tools, including Teams and SharePoint.
• Skills and Abilities:
  • Exceptional organizational, time management, and prioritization skills, with the ability to manage competing demands independently.
  • Proven ability to handle confidential and sensitive information with professionalism, discretion, and sound judgment.
  • Strong judgment and problem‑solving skills, with the ability to anticipate needs and act proactively.
  • Strong written and verbal communication skills, with experience preparing executive‑level correspondence, briefings, and presentations.
  • Self‑motivated, resourceful, and comfortable working independently while supporting a collaborative executive leadership team.
  • Detail‑oriented with a strong commitment to accuracy, follow‑through, and meeting deadlines.
  • Demonstrated ability to exercise sound judgment, manage sensitive issues independently, and escalate matters appropriately.
• Requirements:
  • Clear criminal record check and satisfactory employment references.
  • 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.

Benefits

• 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! We look forward to reviewing your application.

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.

Apply by: February 27, 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.