Managing Director

WinAir; London; Hybrid; CAD 180,000 - 280,000; Full time

Benefits offered by this job

Extended healthcare

EAP

RRSP matching

Flexible work schedule

Summer Friday hours

Job summary

WinAir, based in London, Ontario, is seeking a Managing Director to lead overall strategy, drive growth, and ensure cohesive execution across executive teams in a software/SaaS environment.

You will report to the Board, translate strategy into actionable plans, manage risks, and guide the organization toward operational excellence with a focus on AI-enabled improvements and industry leadership.

Qualifications

• 15+ years of progressive leadership experience, with senior management/executive level responsibilities.
• Proven track record running a software or SaaS operating unit with full P&L ownership.
• Experience operating under a board of directors and producing board-level reporting.
• Demonstrated leadership of multi-functional director teams across Finance, Product, Development, and/or Sales.
• Experience guiding platform transitions, market expansion, or competitive repositioning.
• Aviation, MRO, or regulated vertical B2B experience is a plus.
• Bachelor's in Business; MBA is preferred.

Responsibilities

• Provide top-level strategic leadership and accountability to achieve organizational goals.
• Translate Board-approved strategy into an executable plan with clear priorities and resources.
• Report transparently on performance, risks, and progress to the Board.
• Lead across Finance, Product, Development, and Sales to drive cohesion and results.
• Foster AI adoption and operational transformation across functions.
• Represent WinAir with customers, partners, and industry stakeholders.

Skills

Strategic leadership

P&L ownership

Board reporting

Cross-functional leadership

Change management

Education

MBA

Bachelor's degree in Business

Job description

Vision Statement

To be the global standard in aviation software—powering safe, efficient, and connected operations through innovation, dependability, and passion.

Mission Statement

We deliver intuitive, reliable aviation software that empowers operators and maintenance teams to work smarter. By combining deep industry knowledge with cutting‑edge technology, we streamline operations, ensure compliance, and help our clients keep aircraft flying safely and efficiently.

Our Values

Curiosity – A drive to explore, learn, and innovate by asking questions and seeking better solutions.

Collaboration – Working together openly and respectfully to achieve shared goals and create stronger outcomes.

Dependability – Being reliable, consistent, and accountable in delivering on promises and responsibilities.

Efficiency – Maximizing productivity and resources by working smart, staying organized, and reducing waste.

Passion – Bringing energy, enthusiasm, and dedication to everything we do, inspiring others through commitment.

Candidate must reside in Ontario, Canada

Work in a fast‑paced environment with changing priorities

Be able to work remotely and on‑site upon request

Be able to sit for prolonged periods

Why Work for Us?

We offer acompetitive compensation package based on experience and a proven track record of success relative to the deliverables of the role.

• Benefits offered at WinAir include extended healthcare, dental, EAP, RRSP matching program, etc.

• We are also proud to offer a flexible work schedule, including "Summer Friday hours" maximizing good work‑life balance, different social committee events, and quarterly Town Hall meetings to foster teamwork and a strong, long‑lasting work relationship.

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.

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.

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.