Director- Strategic Projects

Winnifred Stewart is seeking a Director of Strategic Projects to join our dynamic, results-oriented executive management team. This newly created role will shape strategic priorities and lead complex initiatives that drive organizational growth and innovation at a vital social service organizations that ensures people with diverse abilities have a voice, choice and a place to belong for their entire life.

What We Do
Winnifred Stewart walks alongside adults with intellectual disabilities, amplifying their right to belong and fostering community inclusion. Our work is grounded in inclusive decision-making, strong individual relationships, and the courage to challenge conventional norms. We envision a future where individuals with diverse abilities are empowered to express their voices, make choices, and experience a lifelong sense of belonging.

What You Will Do
Reporting to the CEO, the Director of Strategic Projects is a senior leadership role responsible for leading transformative initiatives that support Winnifred Stewart’s long-term sustainability, growth, and innovation. This role is ideal for a seasoned professional with strong business acumen, strategic foresight, and the ability to lead complex, cross-functional initiatives.

Key Areas of Focus

• Strategic board engagement
• Capital planning and asset strategy
• Service growth through partnerships and mergers
• Social enterprise development, including scaling Joey & Friends Empties (processing over 7 million bottles annually)
• Development of a workplan and prioritization framework

Responsibilities

Board Relations & Strategic Reporting

• Serve as a key liaison to the Board of Directors, providing strategic updates, reports, and insights
• Lead the development of organizational reporting frameworks aligned with strategic priorities and community impact

Asset Strategy & Capital Planning

• Develop long-term asset strategies, including capital investments and lease negotiations
• Collaborate with stakeholders to assess infrastructure needs and secure funding
• Partner with Finance on budgets, forecasts, and cost-benefit analyses

Growth & Expansion Strategy

• Develop business cases for service expansion through partnerships, mergers, and contract diversification
• Conduct market and stakeholder analysis to identify growth opportunities

Social Enterprise Development

• Support strategic growth of Joey & Friends Empties
• Identify new revenue opportunities, efficiencies, and engagement strategies
• Assess opportunities to launch new mission-aligned social enterprises

Strategic Planning & Business Strategy

• Oversee implementation of approved strategic initiatives with clear milestones and performance tracking
• Prepare materials for leadership and Board review (RFDs, capital proposals, funding strategies, business plans)
• Lead and advise on mergers, service integration, and resource-sharing initiatives
• Foster cross-departmental collaboration toward shared goals

The Ideal Candidate
You are a collaborative, inclusive leader with strong relationship-building skills, sound judgment, and ethical leadership. You are highly organized, results-focused, and comfortable managing multiple complex initiatives simultaneously.

Required Skills & Competencies

• Strong written and verbal communication
• Senior leadership and Board presentation experience
• Strategic and business planning
• Project and organizational management
• KPI development and performance measurement
• Leadership and people management
• Change management
• Stakeholder engagement
• Analytical, evidence-based decision-making

What You Bring

• Bachelor’s degree in business administration, commerce, public administration, or related field
• 7–10 years of progressive leadership experience in strategic planning, business development and project management
• Proven success leading cross-functional initiatives
• Experience in capital planning, lease negotiations, and stakeholder engagement
• Contract management and legal consultation experience
• Strong financial and analytical skills
• Experience with social enterprise development or scaling
• Not-for-profit sector experience is an asset

Prerequisites

• Valid driver’s license, $2M liability insurance, and access to a personal vehicle
• Clear police clearance (CRIM) within six months or ability to obtain
• Valid driver’s abstract

 Winnifred Stewart is an equal opportunity employer, committed to an inclusive and safe work environment for people of all backgrounds.

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