Description
Winnifred Stewart is seeking a Director of People & Culture to join our mission-driven executive leadership team. This newly created fulltime role will lead and advance our people and culture strategy in alignment with our values, community commitments, and long-term impact.
As a member of the senior leadership team, the Director People & Culture serves as a trusted advisor to the CEO and Board, bringing strategic insight, diverse perspectives, and an equity-informed lens to talent management strategy, culture, organizational change, and people governance.
This role is responsible for ensuring that Winnifred Stewart attracts, develops and retains a diverse, engaged, and capable workforce while fostering a values-led, inclusive, culturally responsive, and psychologically safe environment.
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, trauma-informed practices 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 People and Culture (P&C) is a senior leadership role responsible for shaping and leading transformative people strategies that support Winnifred Stewart’s sustainability, service excellence, and workforce wellbeing.
You will lead a team that consists of two P&C Coordinators and an Engagement and Development Leader. In addition to strategic leadership, this role provides hands-on guidance and operational support to ensure excellence across the full employee lifecycle.
Key Areas of Focus
People & culture leadership
Employee experience and well being
Workforce planning & talent management strategy
Performance, reward & recognition
Employee relations, compliance & risk
Learning and development
Responsibilities
People & culture leadership
Develop and implement a P&C strategy aligned with the agency’s values, mission, and strategic priorities
Embed equity, anti-racism, and culturally responsive practices into people strategies, leadership behaviours, and organizational systems
Champion a culture of care, accountability, collaboration, and continuous learning and belonging
Establish practices that strengthen connection, psychological safety, and inclusive participation across the agency
Leadership & organizational capability
Partner with senior leaders to build strong, values-aligned leadership capability
Design and deliver leadership development programs, coaching, and succession planning strategies
Support leaders in navigating organizational change and growth with confidence and compassion
Employee experience
Oversee the full employee lifecycle, including recruitment, onboarding, development, engagement, retention and exit
Lead initiatives that support wellbeing, psychological safety, and trauma-informed practice
Ensure recruitment and advancement practices are equitable, transparent, and inclusive
Workforce planning & talent
Lead workforce planning to ensure sustainability, capability, and service continuity
Develop talent management strategies, that attracts diverse talent aligned with agency values
Establish a learning and development framework that builds capability and supports career pathways
Performance, reward & recognition
Oversee performance management processes that are fair, supportive, and values-based
Develop and lead a total rewards philosophy that reflects equity, transparency, and organizational sustainability
Employee relations, compliance & risk
Ensure compliance with employment legislation and regulatory requirements
Lead complex sensitive high-risk investigations and formal complaints, with compassion and fairness and cultural awareness
Oversee HR policies, procedures, and governance practices
Governance, reporting & data
Provide high-quality reporting and insights to the CEO and Board
Use HR data and insights to inform decision-making and strengthen organizational effectiveness
Support audits, accreditation, and funding compliance requests, related to P&C matters
Our Commitment to Equity and Inclusion - Winnifred Stewart is committed to building a workforce that reflects the diversity of the communities we serve. We strongly encourage applications from Indigenous, Black, and racialized individuals; persons with disabilities; members of the 2SLGBTQIA+ community; newcomers; and individuals from other equity-deserving groups.
We recognize that systemic barriers may have impacted career pathways and value lived experience alongside professional credentials. Accommodation is available throughout the recruitment and selection process upon request.
Requirements
The Ideal Candidate
You are a collaborative and inclusive leader who values diverse perspectives and builds strong relationships across all levels of the agency. You lead with cultural awareness, humility, and sound judgment, and you are comfortable balancing strategic thinking with hands-on operational support.
You bring a demonstrated commitment to equity, anti-racism, and inclusive leadership, and you understand how power, privilege, and systemic barriers can shape workplace experiences.
You are highly organized, results-focused, and comfortable managing multiple initiatives simultaneously.
Required Skills & Competencies
Strategic business acumen
Experience leading change and shaping healthy workplace organizational culture
Strong communication skills and facilitation skills across diverse audiences
Senior leadership and Board presentation experience
Strategic thinker with hands-on, practical capability
Ability to influence, coach and advise at the executive level
High degree of integrity, discretion, and ethical leadership
What You Bring
Bachelor’s degree in human resources, organizational development, or a related field
8+ years of progressive experience in People & Culture or human resources leadership, with at least 5 years in a leadership role with 2 of those years at a senior level
Broad HR generalist expertise with demonstrated experience driving culture, engagement, organizational effectiveness, leadership development, employee relations, and workforce strategy
Experience embedding equity-informed and inclusive practices into people systems
Experience leveraging HRIS and emerging technologies (including AI) to improve practices
Strong working knowledge of relevant employment legislation (e.g., Human Rights, Employment Standards, Privacy, WCB, and Common Law)
Proven ability to influence, coach, and advise a P&C team, and Winnifred Stewart leaders on sensitive workforce matters
Excellent communication and facilitation skills, with the ability to tailor messaging to diverse audiences
CPHR designation is an asset
Not-for-profit sector experience is an asset
We recognize that leadership pathways are not always linear ad encourage candidate with diverse professional journeys to apply.
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
