Sr. AI Content Strategist

About the role

The Sr. AI Content Strategist leads the design and scaling of content systems that power onboarding experiences across traditional product surfaces and AI-driven interactions. This role sits at the intersection of content strategy, product design, and AI systems, owning frameworks, taxonomy, and structure to enable reusable, scalable, high-quality content. You will drive a large-scale onboarding migration and build the content foundation for AI-powered onboarding, defining how AI-generated content behaves, scales, and is evaluated. This is a hands-on, senior role that combines strategy, system design, and execution to enable product, design, and PM teams.

Responsibilities

• Define content models, taxonomy, and modular frameworks for tagging, reuse, and scalability
• Lead content strategy for a large-scale onboarding migration (ServiceNow/Workday)
• Structure content for immediate usability and AI-readiness
• Develop prompt frameworks, templates, and variation patterns for AI onboarding experiences
• Define personalization logic and content behavior within AI systems
• Establish evaluation criteria and quality benchmarks for AI-generated content
• Direct and guide Content Designer(s) on execution and deliverables
• Create repeatable frameworks, patterns, and documentation for content systems
• Enable product, design, and PM teams to independently apply content systems
• Partner with Product, Design, Engineering, and Change Management teams to align messaging and rollout strategy
• Identify and prioritize new AI-driven content opportunities

Requirements

• 5+ years of experience in content strategy with a product/UX focus
• Experience designing content systems, taxonomy, and structured content
• Hands-on experience with AI-generated content, including working with large language models, prompt design, and personalization
• Proven track record leading content migrations or large-scale system changes
• Strong stakeholder management and communication skills
• Comfortable operating across strategy and hands-on execution
• Experience defining evaluation criteria and quality benchmarks for generated content
• Experience with onboarding, activation, or lifecycle journeys
• Familiarity with ServiceNow or Workday ecosystems
• Experience partnering with change management or internal communications teams
• Engagement & Logistics
• Engagement Length: 12+ months.
• Time Zone: 8 AM to 5 PM - CT / flexible
• Equipment: BYOD (Bring Your Own Device)
• Selection Process
• Meeting with Resilient Co. team.
• First client interview with portfolio.
• client technical interview.
• Possibly a second client interview - Meet & Greet.

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