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Director, Content Strategy Strategy

Job in Winnipeg, Manitoba, Canada
Listing for: Huge
Full Time position
Listed on 2026-09-06
Job specializations:
  • IT/Tech
    AI Business & Operations, AI Engineer (Applied/Software)
Salary/Wage Range or Industry Benchmark: 135000 CAD Yearly CAD 135000.00 YEAR
Job Description & How to Apply Below
Location:

This position is remote within Canada.
Huge is looking for a Director of AI Content Strategy to drive innovation and excellence. This role will lead the development and execution of AI-powered content strategies integral to designing seamless, scalable content ecosystems that deliver measurable results for our clients. As an AI content strategy expert, this role requires a strategic thinker who is an expert in Conversational AI and Generative AI, with a proven track record in AI-driven product experiences.

As a Director, you’ll lead and drive projects that help clients future-proof their content experiences and maximize the value of their content—identifying opportunities, defining strategies, and creating actionable roadmaps to achieve their goals. You’ll define frameworks, steward content governance, craft conversational guidelines, and partner closely with cross-disciplinary teams to bring world-class digital experiences to life.

What you’ll be doing .

Act as a subject matter expert for our internal team and a trusted advisor for day-to-day and senior clients.

Drive content governance, audits, workflow design, and lifecycle management.

Create and evolve information architecture, content models, taxonomy structures, and metadata systems.

Develop strategy, including voice & tone frameworks, messaging guidelines, and systemized content patterns.

Partner with Experience Design, Product, and Engineering teams to scale content operations and ensure quality across channels.

Design and lead conversation strategy for chat, voice, and next-generation agentic experiences.

Build dialogue flows, interaction scripts, guardrails, and error-handling pathways.

Demonstrate an applied understanding of LLM behavior, prompting, context windows, hallucination risks, and model limitations.

Develop golden queries and responses to benchmark quality and ensure safe, consistent outputs.

Create AI content pipelines, including frameworks for governance, training data readiness, and human-in-the-loop review.

Architect intent taxonomies, entity structures, and conversational knowledge hierarchies.

Work directly with engineering and product teams to deploy and optimize experiences across conversational AI platforms (chatbots, voice assistants, agentic systems, etc.).

Lead client relationships as the senior content & AI strategist across engagements.

Identify opportunities for account growth and partner with pitch teams to shape winning proposals.

What we’d like to see.

12+ years in content strategy, UX writing, content design, or adjacent strategic roles, with experience in an agency, consulting, or client services environment.

Proven experience in enterprise-scale content systems, governance, and information architecture.

Expertise in these foundational areas of content strategy:

Content governance, audit, and lifecycle management

Information architecture and content modeling

Editorial strategy and voice/tone frameworks

Expertise in these areas of AI & Conversational Design:

Conversation design and dialogue flow mapping

Understanding of LLM behavior, prompting, and limitations

Experience with conversational AI platforms (chatbots, voice assistants, agentic systems)

Golden query/response development and testing

AI content pipeline strategy

Intent taxonomy

Demonstrated ability to lead multidisciplinary teams and manage large-scale client engagements.

Strong communication skills, with the ability to translate complex systems into simple, compelling narratives.

Comfort working in fast-paced environments and balancing multiple programs simultaneously.

About Huge
Huge is a design and technology company. We create products and experiences that grow the world’s most ambitious brands. We do this by designing experiences for people, not users, and uncovering new sources of growth by leveraging our creative talent, our proprietary platform LIVE and unlocking the advantages brought to us by emerging technologies. We believe all experiences should be intelligent, shoppable and unique to every brand.

Huge’s nearly 1,000 thinkers, tinkerers, makers and creators, have been problem-solving across North America, Europe, and Latin America for over 25 years.…
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