Strategy & Operations Analyst – AI Tools & Automation

Employment Type: Full Time Location Type: [Not Specified] Salary: [Not Specified]

Company Overview

CSC Generation (CSC) is an AI-enabled multi-brand platform that acquires and transforms retailers into profitable, digital-first, consumer-centric businesses. CSC owns and operates more than 10 retail, eCommerce, and wholesale companies, including Sur La Table, One Kings Lane, and Backcountry.

Position Overview

CSC Generation is hiring a Strategy & Operations Analyst – AI Tools & Automation to support one of CSC’s brand CEOs in driving key operational and AI initiatives. This role blends AI product thinking, business intelligence, and project execution. It is ideal for someone early in their career who is both highly analytical and deeply curious.

This is a demanding role, but for the right person—driven, sharp, and eager to learn—there is no ceiling to how quickly you can grow within the organization. You'll work directly with top executives, tackle real business challenges, and build a deep foundation in strategy, operations, and AI product work.

This position will report into the CEO of a CSC Generation brand.

What You Get To Do Every Day

• Partner with the CEO to operationalize strategy and accelerate key priorities.
• Build lightweight, AI-powered internal tools that streamline workflows across functions.
• Create and own project plans, track deliverables, and follow up with stakeholders to ensure execution.
• Analyze trends in sales, marketing, merchandising, and ops to generate actionable insights.
• Use generative AI tools to automate reporting, draft content, and develop workflows.
• Prepare executive updates, dashboards, and internal presentations to guide decision-making.
• Work closely with department leaders to identify repetitive processes and launch automation pilots—replacing manual workflows with scalable, AI-enabled systems.

What You Bring to the Role

• Bachelor's degree in Business, Computer Science, Engineering, or related field.
• 1–3 years of experience in consulting, analytics, bizops, product, or similar high-intensity roles.
• Strong grasp of AI tools (ChatGPT, Claude, Copilot, etc.) and how to integrate them into daily work.
• Familiarity with automation tools (n8n, Zapier, Make.com) and experience designing lightweight workflows.
• Advanced Excel or Sheets skills; SQL, Python, or data visualization a plus.
• Fast learner with strong initiative, accountability, and follow-through.
• Highly organized, detail-oriented, and confident in navigating ambiguity.
• Hunger to grow fast, solve big problems, and learn directly from C-level leaders.

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:

• 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.

Interview Process

• 📞 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.