AI-Native Product Manager

5 days ago

Remote Canada CSC Generation Full time $120,000 - $180,000 per year
CSC Generation Enterprise (CSC) is an AI-enabled multi-brand platform that acquires and transforms legacy businesses into profitable, digital-first, consumer-centric businesses. CSC's platform is purpose built around its core M&A strategy and drives alpha by encoding revenue growth, unit margin management, and other expert-level retail practices into automation and AI. CSC owns and operates more than 10 companies, including Sur La Table, Backcountry, and One Kings Lane. Together, our companies generate $1B+ in revenue and we employ over 2000 people across North America. We are backed by world-class investors and continue to pursue platform and add-on acquisitions at pace.    We are looking for an AI-Native Product Manager who operates beyond the traditional boundaries of product management. This is not a role for requirement writers or roadmap maintainers. This is a role for a system thinker, a hands-on builder, and a strategist with technical fluency in AI—particularly large language models and intelligent automation systems. You will drive the roadmap, prototyping, evaluation, and automation of intelligent product experiences that can only exist in the AI era. You'll work in a high-impact retail and e-commerce environment where business judgment, operational depth, and execution speed matter.   You won't just manage programs—you'll automate them. You won't wait for engineers to explore— you'll prototype it yourself. You won't just ship AI-enhanced features—you'll architect, iterate, and operationalize them to improve business efficiency. This is the next generation of product Management.   This position will report into the Sr. Director of Product & Engineering. What you get to do every day:
  • Deliver AI-native features (e.g., intelligence, personalization, automation, optimization) that drive measurable impact in conversion, margin, operational cost, or customer experience.
  • Build and launch automated program management workflows (e.g., using n8n, workflow orchestrators, Slack automation, or low-code tools) that eliminate manual coordination and increase transparency.
  • Rapidly prototype solutions in-house using AI-native tools and frameworks (e.g., MCP, Claude) to accelerate discovery and reduce cycle time.
  • Lead the development of AI-driven retail and e-commerce applications that reimagine business processes, operational systems, or customer-facing experiences.
  • Actively influence build vs. buy decisions by assessing feasibility, risk, and AI vs non-AI solution tradeoffs.
  • AI Product Strategy: Identify, validate, and prioritize opportunities where AI delivers transformative—not just incremental—value.
  • Prototyping & Experimentation: Rapidly build and test prototypes using AI-native tools and internal system access to validate functionality and business potential.
  • Program Management Automation: Use modern workflow automation tools to reinvent coordination, status reporting, and stakeholder engagement.
  • Cross-Boundary Execution: Partner fluidly across design, engineering, data science, and operations. Lead without waiting for permission.
  • Build-vs-Buy Judgment: Evaluate external vendors and open-source vs internal builds with a critical eye on cost, accuracy, governance, and integration.
What you bring to the role:
  • 2+ years of product management experience, ideally in retail, commerce, or software platforms.
  • Demonstrated experience working with or alongside ML/AI systems and process automation tools.
  • Working knowledge of LLMs, embeddings, agents, and AI-enabling infrastructure.
  • Hands-on experience with AI-native tools such as prompt orchestration platforms, workflow automation tools, or low-code prototyping environments.
  • Proven ability to prototype, test, and scale ideas rapidly.
  • Strong business sense and comfort with ambiguity.
  • Proficiency e-commerce and digital marketing a strong plus. 
What's in it for you?
  • Joining CSC Generation isn't just about having a seat at the table—it's about helping redesign the table entirely. You'll be challenged, stretched, and supported as you grow faster than you thought possible. In addition to competitive compensation, we offer: 
  • You'll help define what modern product management looks like in the AI era—while building tools and experiences that reach hundreds of millions of visitors annually. You'll move fast, learn constantly, and make an outsized impact at a meritocratic company at the forefront of AI, ML, and innovation in a stodgy category.
  • Executive Access: Work directly with brand CEOs and senior leadership, solving real business problems and earning mentorship from top operators. 
  • AI-First Skill Building: Get hands-on with the most advanced AI tools in the market. From automation to prompt engineering, you'll build a modern tech stack that sets you apart in any industry. 
  • Accelerated Career Path: High performers are quickly entrusted with greater responsibility, new challenges, and leadership opportunities across our portfolio of brands. 
  • Competitive benefits: Paid time off policies, 401(k)/RRSP match, medical/dental/vision and a variety of supplemental policies, and employee discounts at our portfolio companies
What our interview process looks like:
  • Step 1: If you align with our vision and meet the qualifications, we'll reach out to schedule a conversation and introduce CSC. 
  • Step 2: You'll complete a short AI or product-building challenge so we can understand how you approach problems and execution. 
  • Step 3: Participate in deep-dive interviews with CSC leadership focused on your experience, product mindset, and operational thinking. 
  • Step 4: Offer. We'll move fast for the right candidate. 
The CSC family of brands provides equal employment opportunities to all employees and applicants for employment and prohibits discrimination and harassment of any type without regard to race, color, religion, age, sex, national origin, disability status, genetics, protected veteran status, sexual orientation, gender identity or expression, or any other characteristic protected by federal, provincial, state or local laws.   The CSC family of brands is committed to providing reasonable accommodations for qualified individuals with disabilities in our job application procedures. If you need assistance or an accommodation due to a disability, please contact [email protected].  We may use artificial intelligence (AI) tools to support parts of the hiring process, such as reviewing applications, analyzing resumes, or assessing responses. These tools assist our recruitment team but do not replace human judgment. Final hiring decisions are ultimately made by humans. If you would like more information about how your data is processed, please contact us.

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