Managing Director

Job Description

Reporting to the Board of Directors, the Managing Director is responsible for the overall leadership and performance of WinAir. This role sets strategic direction, aligns and holds accountable the leaders of each functional area, and ensures the organization operates cohesively toward its goals. The Managing Director works closely with the Board to translate strategy into results and will also support the continued growth and success of the organization by assisting with other duties as assigned.

Responsibilities

Strategic & Executive Leadership

• Provide overall executive leadership for WinAir, accountable to the Board of Directors for organizational performance.

• Translate Board-approved strategy into an executable operating plan, with clear priorities and resource allocation across the organization.

• Provide regular, transparent reporting to the Board on organizational performance, risks, and strategic progress.

• Identify and evaluate opportunities for growth, efficiency, and risk mitigation at the organizational level.

Leading Through Functional Directors

• Set clear expectations and goals for each functional director and hold them accountable for the performance of their respective areas.

• Ensure alignment and coordination across functions, so that plans and priorities are integrated rather than siloed.

• Support functional directors in resolving cross-departmental issues, removing obstacles, and securing resources needed for their teams to succeed.

• Preserve and reinforce each director's ownership and accountability for their function, while ensuring the organization operates as a unified whole.

Organizational Effectiveness

• Build a high-performing, accountable leadership team across all functions.

• Support succession planning and organizational design as the company grows.

• Champion a culture of accountability, collaboration, and continuous improvement across the organization.

• Represent WinAir externally with customers, partners, and industry stakeholders as required.

AI and Operational Innovation

• Champion WinAir's internal adoption of AI tools and workflows, setting the tone from the top that the organization is committed to working smarter and evolving how it operates.

• Work with the director team to identify and implement AI-driven improvements across functions, from sales and marketing to development, operations, and customer support.

• Foster a culture of experimentation and continuous improvement, where the team is encouraged to test, learn, and embed new tools into everyday work.

Qualifications

Education & Experience

• 15+ years of progressive leadership experience, with a significant portion at the senior management or executive level.

• Proven track record running a software or SaaS operating unit with full P&L ownership, not project management or department leadership, but actual accountability for the result.

• Experience operating under a board of directors and producing written board-level reporting on a standing cadence.

• Demonstrated experience directly managing a multi-functional director-level team across Finance, Product, Development, and/or Sales.

• Has led a business or product through significant change such as a platform transition, competitive repositioning, or market expansion.

• Aviation, MRO, or regulated vertical B2B experience is an asset but not required; we will prioritize operating discipline and leadership track record.

• Bachelor's degree in Business, Commerce, or a related field required; MBA an asset.

Skills & Aptitudes

• Strong external presence: comfortable representing the company at the customer, partner, and industry level.

• Comfortable working in a founder-led, family-owned environment where context, history, and relationships matter.

• Demonstrated interest in or experience with AI adoption and operational transformation; a genuine curiosity about how emerging tools can change the way a business works.

Additional Information

To ensure your application is properly received please apply by visiting https://winair.ca/careers/ and select “apply now” on the appropriate position.

Thank you in advance for your interest. Only those candidates selected for an interview will be contacted. If you require any accommodation at any point of recruitment process, please let us know.