***Currently Reviewing Candidates - No longer accepting applications*** Director Of Strategic Projects

We envision a future where individuals with diverse abilities are empowered to express their voices, make choices, and find a sense of belonging throughout their lives.  Winnifred Stewart has a new strategic plan 2023-2028 that describes a bright future and is transformational in nature.

Winnifred Stewart is seeking a dynamic and results-oriented leader to join our executive team as Director of Strategic Projects. This role is ideal for a seasoned professional with strong business acumen, strategic foresight, and a proven ability to lead complex initiatives that drive organizational growth and innovation. 

The Director of Strategic Projects will lead transformative initiatives that support long-term sustainability and expansion. Key areas of focus include strategic board engagement, capital planning, service growth through partnerships and mergers, and the development of social enterprise initiatives—particularly enhancing the impact and scalability of Joey & Friends Empties, Winnifred Stewart’s bottle collection business, which currently processes over 7 million bottles annually. A key part of the position will be scoping out a workplan and a prioritization matrix for the role.

Key Responsibilities

All of the following responsibilities will be done in collaboration with the Executive Leadership Team at Winnifred Stewart:

Board Relations & Strategic Reporting

-Serve as a key liaison to the Board of Directors, providing strategic updates, reports, and insights to support governance and decision-making. 

-Lead the development of organizational reporting frameworks that align with strategic priorities, performance metrics, and community impact.  

Asset Strategy & Capital Planning

-Lead the exploration and development of long-term asset strategies, including capital investment opportunities and lease negotiations.

-Collaborate with internal and external stakeholders to assess infrastructure needs and secure funding for future growth.

-Partner with Finance to develop project budgets, forecasts, and cost-benefit analyses for major strategic initiatives.

Growth & Expansion Strategy

-Develop and present business cases to expand the reach of Winnifred Stewart’s services through strategic partnerships, mergers, and diversification of government contracts. 

-Conduct market and stakeholder analysis to identify opportunities for service innovation and expansion. 

-Embed equity, diversity, and inclusion principles in strategic projects, partnerships, and growth planning. 

Social Enterprise Development

-Support the strategic growth of Joey & Friends Empties, Winnifred Stewart’s bottle collection social enterprise. 

-Identify new revenue-generating opportunities, operational efficiencies, and community engagement strategies to enhance the enterprise’s impact and sustainability. 

-Explore and assess opportunities to launch new social enterprises that align with Winnifred Stewart’s mission and create meaningful employment and community impact. 

Strategic Planning & Business Strategy

-Demonstrate ability to lead strategic & business planning processes and align departmental goals with Winnifred Stewart’s

long-term vision and mission.

-Oversee the implementation of approved strategic initiatives, ensuring clear milestones, resourcing, and performance tracking.

-Expertise in developing financial methodologies for performance monitoring and measurement across business units.

-Skilled in preparing executive decision-making frameworks, including the evaluation and analysis of qualitative and quantitative data to support strategic choices.

-Proven experience in developing comprehensive evaluation materials for leadership and Board review, including Request for Decision, capital acquisition proposals, funding strategies, and business plans.

-Apply change management best practices to ensure organizational readiness and adoption of new initiatives.

-Ability to lead and advise on mergers, service integration, and resource-sharing initiatives to enhance organizational efficiency and impact.

-Experience in drafting and advising on internal policies that support sound governance and compliance with Board directives.

-Collaborative partner to the Executive Leadership team in shaping and executing Winnifred Stewart’s strategic direction.

-Strong capacity to influence and align cross-functional teams with organizational values and strategic priorities.

-Adept at fostering cross-departmental collaboration to drive unified progress toward strategic goals.

-Skilled in stakeholder relations, acting as a liaison between Winnifred Stewart and shareholders, funders, and external partners.

Risk Management

-Proficiency in developing and maintaining organizational risk matrices and leading risk reduction planning initiatives.

-Experience in contract management, legal consultation, and ensuring agreements meet service standards, legal requirements, and budget constraints.

-Ability to identify, assess, and report risk issues to executive leadership and Board committees.

-Strategic understanding of organizational risk profiles and the ability to implement safeguards that protect long-term sustainability.

Leadership

-Proven ability to collaborate with executive leadership to foster alignment and commitment to organizational goals.

-Experience in implementing and managing departmental objectives, KPIs, and performance measures.

-Commitment to cultivating a service-oriented, collaborative, and innovative workplace culture.

-Dedication to maintaining a safe and inclusive work environment in alignment with Winnifred Stewart’s Health & Safety Program.

-Strong leadership presence with the ability to inspire and guide teams through change, growth, and strategic transformation.

Requirements Profile (Competencies, skills, abilities, experience, education necessary.) 

Skills & Abilities 

-Strong interpersonal and communication skills; experience in effectively communicating key data, including presentations to senior management, Board, and/or external stakeholders. 

-Personal qualities of integrity, credibility, and commitment to WS’s mission.

-Proactive, hands-on strategic thinker who will conceive and implement new ideas.

-Solutions and detail-oriented individual with a high degree of professionalism and diplomacy.

-Keen analytic, organization, and problem-solving skills which allows for strategic data interpretation. 

-Tact, diplomacy, confidentiality, and good judgement when dealing with information pertaining to finance, employees, and the organization. 

-Initiative and ability to think critically and act logically in evaluating situations and generating required steps to ensure success. Proficient command/comprehension of the English language. 

-Proficient command/comprehension of the English language.

Education & Experience 

-Bachelor’s degree in Business Administration, Commerce, Public Administration, or a related field. 

-Minimum 7–10 years of progressive leadership experience in strategic planning, business development, or corporate project management.

-Proven track record of leading complex, cross-functional initiatives with measurable outcomes.

-Experience in capital planning, lease negotiations, and stakeholder engagement.

-Strong financial acumen and analytical skills, with the ability to develop and present compelling business cases.

-Experience with social enterprise development or operational scaling is a strong asset.

-Exceptional communication and interpersonal skills, with the ability to build trust and influence at all levels. 

Work Environment

-Position is primarily an in-office working arrangement with the ability to have a flexible work schedule to work at home

-Minimal physical demands: periods of keyboarding and use of office equipment.

-Ability to travel to different sites.

-Valid driver’s license, proof of $2 million liability insurance and use of personal vehicle.

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