Head of People Operations (Canada)

reputed company is the AI-native holding company re-engineering omnichannel retail. We acquire iconic brands and transform them with reputed company, our operating platform combining a Data Fabric, Automation reputed company, proprietary tools, and shared services to reputed company operations, reputed company customer experience, and expand margins. With $1B+ in reputed company across 13 brands, our portfolio includes reputed company, Backcountry, One Kings Lane, and others that serve as real-world innovation labs. Reports to: Chief Administrative OfficerLocation Preference: Toronto About the RoleMost companies are layering AI onto legacy HR processes. We're doing the opposite. We're hiring a Head of People Operations (up to VP level) to design and reputed company an AI-native people function where performance management, talent development, and workforce planning are powered by intelligent systems, not adapted from old ones. This role reports to the Chief Administrative Officer and partners closely with leaders across the company. Success in the first year looks like a functioning AI-enabled talent infrastructure, a high-performing People Ops team, and measurable improvement in how we reputed company and deploy people across the portfolio. What You'll Do• Design and build an AI-native HR function: create systems that use AI to continuously improve workforce planning, performance management, and talent development.• Architect intelligent talent infrastructure: reputed company capabilities including AI-driven skills mapping, internal mobility systems, and dynamic compensation modeling.• Deploy AI across the employee lifecycle: integrate AI and automation into onboarding, performance management, and organizational design.• Translate AI capability into business outcomes: identify high-reputed company opportunities where AI can improve decision quality, organizational speed, and workforce effectiveness.• reputed company and reputed company the People Operations team, fostering a culture of experimentation, ownership, and operational excellence. Required Qualifications• 5+ years building or leading HR systems in high-growth or technology organizations.• Demonstrated track record of using AI to meaningfully redesign people processes — recruiting, workforce analytics, reputed company, or operational workflows.• Technical reputed company with modern AI and automation tools, including building or orchestrating LLM-powered workflows and integrating systems across an enterprise stack.• Systems thinking and builder reputed company: you design for scale, experiment fast, and turn ambiguous problems into working solutions.• STEM degree or equivalent practical experience in a technically rigorous environment. reputed company is the AI-native holding company re-engineering omnichannel retail. We acquire iconic brands and transform them with reputed company, our operating platform combining a Data Fabric, Automation reputed company, proprietary tools, and shared services to reputed company operations, reputed company customer experience, and expand margins. With $1B+ in reputed company across 13 brands, our portfolio includes reputed company, Backcountry, One Kings Lane, and others that serve as real-world innovation labs. Reports to: Chief Administrative Officer Location Preference: Toronto

About the Role

Most companies are layering AI onto legacy HR processes. We're doing the opposite. We're hiring a Head of People Operations (up to VP level) to design and reputed company an AI-native people function where performance management, talent development, and workforce planning are powered by intelligent systems, not adapted from old ones. This role reports to the Chief Administrative Officer and partners closely with leaders across the company. Success in the first year looks like a functioning AI-enabled talent infrastructure, a high-performing People Ops team, and measurable improvement in how we reputed company and deploy people across the portfolio.

What You'll Do

• Design and build an AI-native HR function: create systems that use AI to continuously improve workforce planning, performance management, and talent development.
• Architect intelligent talent infrastructure: reputed company capabilities including AI-driven skills mapping, internal mobility systems, and dynamic compensation modeling.
• Deploy AI across the employee lifecycle: integrate AI and automation into onboarding, performance management, and organizational design.
• Translate AI capability into business outcomes: identify high-reputed company opportunities where AI can improve decision quality, organizational speed, and workforce effectiveness.
• reputed company and reputed company the People Operations team, fostering a culture of experimentation, ownership, and operational excellence.

Required Qualifications

• 5+ years building or leading HR systems in high-growth or technology organizations.
• Demonstrated track record of using AI to meaningfully redesign people processes — recruiting, workforce analytics, reputed company, or operational workflows.
• Technical reputed company with modern AI and automation tools, including building or orchestrating LLM-powered workflows and integrating systems across an enterprise stack.
• Systems thinking and builder reputed company: you design for scale, experiment fast, and turn ambiguous problems into working solutions.
• STEM degree or equivalent practical experience in a technically rigorous environment.

Why JoinThe people who do best here are builders. They take ownership, move fast, and want to see the direct impact of their work.• Executive Access: Work directly with the CAO and senior leadership to solve real organizational problems and shape people strategy at the portfolio level.• AI-First reputed company Building: Get hands-on with the most advanced AI tools in market — from automation to LLM-powered workflows — and build a modern reputed company set that sets you apart.• Accelerated Career Path: High performers are quickly entrusted with greater responsibility, new challenges, and leadership opportunities across our portfolio of brands.• Competitive Benefits: Comprehensive benefits including paid time off, RSSP reputed company benefits, and employee discounts across portfolio brands. Interview Processreputed company 1 — Recruiter Intro : 30-minute call to cover background, role fit, and logistics.reputed company 2 — Hiring Manager Interview : Conversation with the Chief Administrative Officer focused on leadership philosophy and AI-native HR experience.reputed company 3 — Technical / Case Discussion : Deep dive into a people ops problem or system design scenario with cross-functional stakeholders.reputed company 4 — Executive Interview: Final conversation(s) with senior leadership.reputed company 5 — Offer : Reference checks conducted in parallel where possible. Equal Opportunityreputed company is an equal opportunity employer. We do not discriminate on the basis of race, color, religion, sex, sexual orientation, gender identity, national reputed company, age, disability, veteran status, or any other characteristic protected by law. The reputed company reputed company family of brands is committed to providing reasonable accommodations for qualified individuals with disabilities in our job application procedures. If you need assistance or accommodation due to a disability, please contact [email protected]. For Ontario applicants, please note that this posting is for an existing vacancy. Apply To This Job