Cscgeneration 21mo ago

Head of People Operations (Canada)

CanadaRemoteFull Timeexecutive

OperationsManagementPeople Operations

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Quick Summary

Overview

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,

Technical Tools

OperationsManagementPeople Operations

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

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.

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: foster a culture of experimentation, ownership, and operational excellence across a high-performing HR function.

5+ years building or leading HR systems in high-growth or technology organizations, including at least 2 years in a senior leadership capacity.

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.

Proven ability to design scalable systems, run structured experiments, and translate ambiguous organizational problems into working solutions.

STEM degree or equivalent experience in a technically rigorous environment.

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, RRSP match, group benefits, and employee discounts across portfolio brands.