Head of People Operations (Canada)

CSC Generation is the AI-native holding company re-engineering omnichannel retail. We acquire iconic brands and transform them with Genesis, our operating platform combining a Data Fabric, Automation Engine, proprietary tools, and shared services to modernize operations, elevate customer experience, and expand margins. With $1B in revenue across 13 brands, our portfolio includes Sur La Table, 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 lead 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 develop 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: develop 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-leverage opportunities where AI can improve decision quality, organizational speed, and workforce effectiveness.

• Lead and develop 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, knowledge management, or operational workflows.

• Technical fluency with modern AI and automation tools, including building or orchestrating LLM-powered workflows and integrating systems across an enterprise stack.

• Systems thinking and builder mindset: 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 Join

The 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 Skill Building: Get hands-on with the most advanced AI tools in market — from automation to LLM-powered workflows — and build a modern skill 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 match, group benefits, and employee discounts across portfolio brands.

Interview Process

Step 1 — Recruiter Intro 📞: 30-minute call to cover background, role fit, and logistics.

Step 2 — Hiring Manager Interview 💬: Conversation with the Chief Administrative Officer focused on leadership philosophy and AI-native HR experience.

Step 3 — Technical / Case Discussion 🧠: Deep dive into a people ops problem or system design scenario with cross-functional stakeholders.

Step 4 — Executive Interview: Final conversation(s) with senior leadership.

Step 5 — Offer 📩: Reference checks conducted in parallel where possible.

Equal Opportunity

CSC Generation is an equal opportunity employer. We do not discriminate on the basis of race, color, religion, sex, sexual orientation, gender identity, national origin, age, disability, veteran status, or any other characteristic protected by law.

The CSC Generation 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 hrbenefits@cscshared.com.

For Ontario applicants, please note that this posting is for an existing vacancy.