Cscgeneration 27d ago

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Director of AI Creative Systems

CanadaRemoteFull Timeexecutive

OtherCreative

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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

OtherCreative

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 Growth Officer

Location: Austin, TX (Remote); Toronto, ON (Remote); All other US & Canada (Remote)

We are building a new creative production and testing capability from scratch — one that uses AI-native workflows to generate photoreal imagery, video, and copy at speed, then connects that output to structured testing loops across paid media, email, and site. This function does not exist yet, and the person in this role will define and build it.

As Director of AI Creative Systems, you will architect the end-to-end system that moves creative from brief to prompt to asset to launch, establish the quality bar, and personally ship the first generation of production-grade work. Success in the first year means creative output that is materially faster and cheaper without looking cheap, repeatable testing systems that increase learning velocity, and stronger integration between creative generation and commercial decision-making across our portfolio of brands.

This is a lean team. You will own a lot, move fast, and make decisions with full end-to-end responsibility.

Design and implement AI-native workflows for image, video, copy, resizing, versioning, QA, approvals, and deployment.

Build the full pipeline from brief to prompt to asset to review to launch — starting with your own hands before scaling through others.

Establish standards for prompts, references, model selection, asset naming, storage, metadata, and quality control.

Create reusable templates, playbooks, and automations so brands can scale output without rebuilding the system every time.

Train internal teams to operate within those systems rather than relying on one-off heroics.

Produce and direct AI-generated creative that meets brand standards and holds up next to traditionally produced work.

Push for photoreal, commercially usable output rather than obvious AI-looking artifacts.

Develop workflows for product imagery, concepting, lifestyle scenes, motion, and derivative asset generation across channels.

Make deliberate decisions about when to use AI-only workflows, hybrid human-plus-AI workflows, or traditional production based on quality and brand risk.

Build systems that generate creative variants for testing across paid social, display, email, landing pages, and other growth channels.

Partner with performance marketing and growth teams to connect creative concepts to test design, campaign structure, naming, routing, and readouts.

Increase testing throughput without destroying learning quality.

Develop segmentation-aware creative workflows that tailor concepts, formats, hooks, or offers to different audiences while staying within legal, platform, and brand guardrails.

Help the organization move from subjective creative debates to structured experimentation and measurable creative learning.

Work closely with growth, performance marketing, ecommerce, merchandising, brand, and leadership teams to identify and remove creative bottlenecks slowing growth.

Translate emerging tools into practical operating leverage instead of trend-chasing.

Stay hands-on enough to ship the first wins yourself while building infrastructure others can use.

Act as both function owner and dangerous builder: set the bar, build the system, and prove it in live work.

7+ years of experience spanning creative production, performance creative, design systems, automation, or AI-enabled content workflows.

Clear evidence of building end-to-end creative systems — not just using AI tools ad hoc or running isolated experiments.

Strong creative taste and quality bar, especially for imagery that must feel premium and commercially usable.

Hands-on experience with generative image, video, and copy tools, including prompt design, reference control, iteration strategy, and QA.

Proven ability to move from concept to shipped workflow, with evidence that the system improved output quality, throughput, cost, or testing velocity.

Experience building creative workflows that connect to paid media testing, performance measurement, or experimentation systems.

Ability to produce or direct photoreal creative output that minimizes obvious AI artifacts.

Strong operator mindset: you can architect systems, personally execute, and raise the standard for others.

Comfort working across creative, technical, and growth stakeholders without needing a large team beneath you.

Experience with Meta creative testing, paid social experimentation, or performance creative operations.

Experience building audience-specific creative workflows and variant-generation systems for advertising.

Experience in ecommerce, retail, lifestyle, home, fashion, or design-led consumer brands.

Familiarity with automation tooling, APIs, structured prompts, and workflow orchestration.

Experience training non-technical creative or marketing teams to use AI systems effectively.

Familiarity with brand-safety, ad-policy, and compliance constraints relevant to creative personalization.

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 Chief Growth Officer and C-suite leadership on real growth and production bottlenecks across the portfolio.

AI-First Environment: Operate in a company actively building with automation, agents, data systems, and modern AI workflows — not running innovation theater.

Portfolio-Scale Ownership: Shape creative strategy across 13 brands, building systems that create measurable commercial impact at scale.

Competitive Benefits (US): Paid time off policies, 401(k) match, medical/dental/vision and a variety of supplemental policies, and employee discounts across our portfolio of brands.

Competitive Benefits (Canada): Paid time off policies, RRSP match, medical, dental, and vision coverage, a variety of supplemental benefit options, and employee discounts across our portfolio of brands.

Recruiter Screen - A 30-minute conversation with our recruiting team to align on the role, your background, and what you are looking for.
Hiring Manager Interview - Discussion with the Chief Growth Officer focused on systems thinking, creative quality bar, and operating style.
Portfolio Review - Walkthrough of shipped work, workflows, and before/after examples showing the quality and leverage of your systems. May be combined with hiring manager review.
Practical Exercise - Live or take-home exercise involving creative workflow design, asset judgment, and testing-system thinking.
Executive Interview - Conversation(s) with CSC Generation leadership.
In-Person Interview - We'd like to meet you at our Austin or Toronto office. Details and logistics will be arranged with your recruiter.
Reference Checks - Conducted in parallel with the final stages where possible.
Offer - We move quickly for the right candidate.