Director - People and Culture

Director People & Culture

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

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

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.