Enablement Senior Specialist, AI and Automation

Overview

At WHOOP, we're on a mission to unlock human performance. WHOOP empowers members to perform at a higher level through a deeper understanding of their bodies and daily lives.

As a Knowledge Enablement Specialist, AI & Automation, you’ll play a critical role in shaping how our knowledge is consumed by AI systems. This role focuses on enabling high-quality, empathetic, and effective automated member support by optimizing knowledge content for AI retrieval, summarization, and resolution—ultimately improving AI CSAT, resolution rates, and member sentiment.

You’ll work closely with the Knowledge Management team, Software, Membership Services Operations, QA, and Product partners to analyze AI performance trends, identify content-driven failure points, and develop scalable frameworks that help our AI systems resolve member issues accurately and consistently. You’ll also partner cross-functionally to distinguish content-driven issues from model or tooling limitations, ensuring ownership is clear and improvements are appropriately targeted.

• Own and evolve AI knowledge standards and frameworks for writing and structuring knowledge content optimized for AI agents ensuring content is clear, retrievable, and aligned with member-facing tone and policy requirements.
• Review AI CSAT, resolution rate, and member sentiment trends to identify recurring issues, content gaps, or structural weaknesses. Establish regular review cadences to track AI content performance over time. Conduct deeper dives into low-performing or escalated AI interactions when needed.
• Translate insights from AI performance analysis into actionable content recommendations. Partner with Content Specialists to request and guide updates that improve AI outcomes.
• Own and deliver AI-related knowledge initiatives, such as readiness audits, framework pilots, or structured content tools. Document outcomes and share learnings with the team to support scalable improvement.
• Work closely with specific teams to align content strategy with AI capabilities, limitations, and roadmap priorities. Surface risks, dependencies, and opportunities related to AI knowledge usage early.
• Contribute to playbooks, guidelines, and training materials that help the Knowledge team write more effective AI-ready content. Act as a subject-matter expert on how AI systems consume and interpret knowledge.
• Actively contribute to team meetings and AI working sessions, bringing insights, learnings, and recommendations to the group. Stay informed through Slack and documentation to continuously synthesize new knowledge and share insights with the team.

• Exceptional writing skills with a demonstrated ability to adapt tone and structure for both human readers and AI consumption.
• Experience using AI-powered tools to review, manage, and optimize content, ensuring accuracy, consistency, and alignment with both human and automated consumption.
• Understanding of how content structure, chunking, and metadata impact AI retrieval, summarization, and response quality.
• Ability to think beyond individual articles and focus on frameworks, patterns, and scalable improvements across the knowledge base.
• Comfort analyzing performance data, trends, and qualitative feedback to identify root causes and translate insights into action.
• Proven ability to work effectively with stakeholders across Ops, QA, Product, and AI-focused teams.
• Experience creating or optimizing structured content (e.g., KB articles, scripts, frameworks) in a complex or fast-changing environment.
• Comfortable working in an evolving AI-driven space, balancing experimentation with accuracy, compliance, and member experience.
• Highly motivated, proactive, and able to manage multiple initiatives in a fast-paced, startup-like environment.

This position will be in person at the WHOOP office in Boston, Massachusetts, or Limerick, Ireland. Candidates must live in the Greater Boston Area or the Limerick region, or be open to relocation and eligible to work in either location.

Interested in the role, but don’t meet every qualification? We encourage you to still apply! At WHOOP, we believe there…