Executive Director

Executive Director

Full-Time | Senior Executive Leadership Role

Location: Winnipeg, Manitoba
Employment Type: Full-Time, Permanent
Compensation: Negotiable, based on experience and qualifications

Position Overview

Staffmax is hiring an Executive Director on behalf of one of its clients in Winnipeg, Manitoba.

This is a senior executive leadership opportunity for an experienced and strategic leader who can guide a member-based non-profit organization through continued growth, modernization, and organizational development.

Reporting to the President and volunteer Board of Directors, the Executive Director will provide overall strategic direction, operational leadership, financial oversight, and external representation. The successful candidate will lead a small professional office team of approximately 2–3 employees while working closely with volunteer member clubs, government representatives, industry partners, and other stakeholders.

A key focus of this position will be strengthening government relations, leading advocacy initiatives, securing funding opportunities, and positioning the organization as a trusted partner in sustainable trail development, tourism, and outdoor recreation.

Key Responsibilities

Strategic Leadership & Governance

• Provide strategic leadership and direction to support the organization's long-term growth and sustainability.

• Lead advocacy initiatives and engagement with municipal, provincial, and federal governments.

• Provide strategic advice to the Board of Directors on governance, policies, risk management, and organizational development.

• Act as the primary liaison between the Board, staff, and member organizations.

• Promote transparent communication, accountability, and effective decision-making.

Organizational & Staff Leadership

• Lead, supervise, and support a professional office team of approximately 2–3 employees.

• Oversee recruitment, performance management, employee development, and human resource functions.

• Establish and maintain effective organizational policies, systems, and procedures.

• Manage fluctuating workloads and allocate resources efficiently.

• Foster a collaborative, accountable, and positive workplace culture.

Operations & Program Management

• Oversee daily operations, including provincial programs, permits, safety initiatives, and organizational communications.

• Identify opportunities for modernization, innovation, and continuous improvement.

• Develop and implement new programs and pilot initiatives.

• Lead and expand corporate sponsorship and partnership opportunities.

• Manage and promote the organization across social media platforms.

• Serve as the primary point of contact for media inquiries and interviews.

• Evaluate existing programs and identify opportunities to improve operational efficiency.

• Provide ongoing leadership and support to member clubs across the province.

Government Relations, Advocacy & Business Development

• Build and maintain strong relationships with municipal, provincial, and federal government representatives.

• Lead government engagement strategies to advance organizational priorities and long-term sustainability.

• Identify, pursue, and secure grants, funding opportunities, and government support.

• Develop policy proposals, briefing materials, and implementation strategies.

• Support negotiations involving agreements, funding programs, and policy frameworks.

• Advocate for trail access, infrastructure investment, tourism development, and sustainable outdoor recreation.

Financial Management

• Develop, prepare, and manage annual operating and capital budgets.

• Oversee financial reporting, controls, audits, and regulatory compliance.

• Ensure responsible management of organizational revenues, funding, grants, and sponsorship contributions.

• Provide financial updates and recommendations to the Board of Directors.

• Maintain strong financial accountability and organizational sustainability.

National & International Representation

• Represent the organization at provincial, national, and international industry events.

• Develop relationships with national and international snowmobiling, tourism, and outdoor recreation organizations.

• Participate in industry forums, conferences, and events.

• Support initiatives focused on safety standards, trail sustainability, tourism development, and innovation.

Qualifications & Experience

• Demonstrated senior leadership experience, preferably within a non-profit, association, membership-based, or comparable organization.

• Experience working effectively with volunteer Boards of Directors, staff teams, and diverse stakeholder groups.

• Proven experience engaging with municipal, provincial, and federal governments.

• Strong background in government relations, advocacy, policy development, or program delivery.

• Demonstrated financial management experience, including budgeting, financial oversight, and audited financial statements.

• Excellent written and verbal communication skills, with the ability to present to senior decision-makers and represent an organization publicly.

• Experience representing an organization at provincial, national, or international levels.

• Experience implementing lean principles, operational improvements, and organizational modernization.

• Knowledge of snowmobiling, trail systems, outdoor recreation, or tourism would be considered a strong asset.

• Post-secondary education in Business Administration, Public Administration, or a related field is preferred. An equivalent combination of education and experience will also be considered.

Ideal Candidate Profile

The successful candidate will be:

• A strategic and forward-thinking leader with strong business and organizational skills.

• A relationship builder who can work effectively with government officials, Board members, volunteers, and industry partners.

• A confident communicator and public representative.

• Financially knowledgeable with strong budgeting and resource management capabilities.

• A proactive problem-solver who embraces modernization and continuous improvement.

• Passionate about organizational growth, community engagement, and sustainable outdoor recreation.

Compensation

Compensation is negotiable and will be commensurate with the successful candidate's experience, leadership capabilities, and overall qualifications. A competitive compensation package will be offered to attract an experienced executive leader.

How to Apply

Interested candidates are invited to apply through Staffmax by submitting their resume and a cover letter outlining their qualifications and interest in the opportunity.

Please note that only candidates selected for an interview will be contacted.

Staffmax is an equal opportunity employer and welcomes applications from qualified candidates.