Managing Director
HybridLondon, Ontario, Canada
Job Summary
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. Hold functional directors accountable for their areas, ensure cross-function alignment, and champion a culture of accountability and continuous improvement. Champion internal adoption of AI tools and workflows, working with the director team to identify and implement AI-driven improvements across sales, development, and operations. Represent WinAir externally with customers, partners, and industry stakeholders as required. Reporting to the Board, this role sets strategic direction and supports organizational growth. The position requires 15+ years of progressive leadership experience, including full P&L ownership of a software or SaaS unit. Candidates must reside in Ontario, Canada, and report to the Board on a standing cadence.
Required Qualifications
- Candidate must reside in Ontario, Canada
- 15+ years of progressive leadership experience
- Proven track record running a software or SaaS operating unit with full P&L ownership
- 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
- Bachelor's degree in Business, Commerce, or a related field
Desired Qualifications
- MBA
- Aviation, MRO, or regulated vertical B2B experience
- 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
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