The AI Holding Company re-engineering retail
Chicago, IL
CSC Generation is the AI-native holding company re-engineering omni-channel retail. We acquire iconic brands and transform them with Genesis—our operating platform unifying 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 more—premier home and outdoor banners that double as real-world innovation hubs. CSC Generation continues to grow through M&A, revitalizing companies with strong brand recognition and loyal customers. We’re building the next-generation technology conglomerate where proprietary AI is the operating system. We have offices in Austin, Chicago, Los Angeles, Salt Lake City, Seattle, and Toronto. Our VC investors include Altos Ventures, Maveron, and Khosla Ventures. We’re always looking for exceptional builders, operators, and technologists to join us.
Hybrid
You will build and maintain scalable AI-accelerated test automation suites using Playwright and integrate quality gates into CI/CD pipelines. Additionally, you will perform exploratory testing and partner with engineering teams to embed quality practices early in the SDLC.
Remote · Canada
The Email & SMS Specialist will own the end-to-end lifecycle of campaigns, including calendaring, creative build, testing, and deployment. They will also monitor performance metrics and lead the adoption of AI-driven workflow improvements to scale team productivity.
Remote · Canada, United States
The Business Development Executive will own the end-to-end acquisition of new B2B accounts within the trade and hospitality sectors. They will utilize AI-driven workflows to build pipelines, manage high-touch relationships, and coordinate with internal teams to drive recurring revenue.
Hybrid · Toronto
You will build and integrate AI-aware security tooling into CI/CD pipelines and AWS infrastructure to detect and remediate threats in real time. Additionally, you will partner with engineering teams to translate security findings into actionable guidance and maintain the full lifecycle of security tools.
Remote · Canada, United States
The Group Sales Account Manager will own the full sales cycle from lead development to closing, managing a pipeline of corporate and industry accounts. They will build repeatable sales processes, meet revenue targets, and coordinate inventory needs with vendor partners.
Hybrid
The Sales Development Representative will own the top of the funnel by prospecting, conducting outreach, and qualifying leads to build a robust sales pipeline. They will manage outbound campaigns across multiple channels and hand off qualified opportunities to Account Managers.
Remote · Canada, United States
You will own the end-to-end search strategy and execution for executive and highly specialized roles across the company's portfolio. This involves proactively sourcing passive candidates, partnering with hiring executives to define role profiles, and managing the entire process from intake to offer.
Remote · Canada, United States
Manage paid acquisition and retention channels including Meta, Pinterest, and Google while maintaining budget accountability. Utilize AI tools to automate reporting and optimization workflows to scale performance across multiple platforms.
Hybrid · Toronto
You will build closed-loop decision systems that estimate causal responses and quantify uncertainty to automate commercial decisions. The role involves developing models for pricing, inventory, and marketing while ensuring systems learn from their own interventions.
Remote · Canada, United States
The Vice President of Performance Marketing will own the paid media P&L and multi-year strategy across all brand banners to drive revenue and margin targets. They will lead a team of marketing professionals and agency partners while collaborating with cross-functional leadership to optimize the customer experience and media efficiency.
Hybrid · Toronto
The Chief of Staff will act as a connective system between company strategy, technology strategy, and day-to-day execution for the CEO and CTO. Responsibilities include managing the executive decision system, overseeing operational cadence, and driving high-priority cross-functional initiatives.
Hybrid · Toronto
Design, deploy, and own production-grade AI automations and tooling across marketing, operations, and logistics. Build AI-agent architectures and reusable connectors to streamline manual business processes and improve operational efficiency.
Remote · United States, Canada
Serve as the technical owner for a core area of the retail service cloud, setting architectural direction and maintaining quality standards. You will design and ship features daily while mentoring junior engineers and managing the product roadmap.
Hybrid · Toronto
Lead end-to-end M&A transactions from LOI to close and develop sector-specific investment theses to generate proprietary deal flow. Partner with portfolio company operators to design and execute value-creation roadmaps and 100-day plans.
Remote · Ontario, Canada
The Director will define how data, insights, and AI drive decision-making across the company, serving as the analytical hub for eCommerce, Marketing, Finance, and Operations. This role is responsible for establishing analytical standards, governing AI-enabled workflows, and transforming data into actionable business recommendations.
Remote · Ontario, Canada
The Director of AI Analytics will define how data and AI drive decision-making across the company, serving as the analytical hub for departments like eCommerce, Marketing, and Finance. This role is responsible for establishing analytical standards, governing AI-enabled workflows, and ensuring data integrity to transform insights into actionable business recommendations.
