Hiring: Director, Enablement- Membership Services Company: WHOOP Location: Boston, MA Job Posted Time: 2026-09-10 11:48:43 Target Skills & Keywords : Content Strategy, Digital Transformation, Stakeholder Management About the job Experience: •10+ years of experience across customer experience, customer support technology, service operations, product operations, digital transformation, or related functions, including 5+ years of people leadership in a fast-paced, high-growth environment. Required Skills: •Define and lead the technology and AI enablement strategy for Membership Services, establishing a roadmap that improves member servicing journeys, reduces friction, increases resolution efficiency, and enables MS teams to consistently deliver a premium service experience at scale. •Serve as the DRI for AI-powered member servicing, including the WHOOP AI support agent, owning its strategy, performance, accuracy, knowledge inputs, capabilities, and ongoing optimization while identifying opportunities to expand effective AI-assisted and automated resolution across the member journey. •Own and continuously improve the Membership Services technology ecosystem, evaluating and optimizing the tools, platforms, integrations, workflows, and automation that enable MSRs and operational teams to serve members efficiently and effectively. •Lead Knowledge & Content strategy for human and AI servicing, ensuring WHOOP product and policy knowledge is structured, accurate, accessible, and optimized to power consistent, high-quality resolution across self-service, AI, and human support experiences. •Identify and eliminate friction across end-to-end member servicing journeys, using member feedback, operational data, servicing trends, and emerging technology to prioritize opportunities and partner cross-functionally on solutions that improve member sentiment, resolution, and effort. •Partner deeply with Product, Business Technology, AI Software, Business Analytics, and Operations to translate Membership Services needs into scalable technology solutions, influence product and platform roadmaps, and ensure new capabilities deliver measurable improvements for both members and internal teams. Qualifications: •Demonstrated success in using technology, AI, automation, or digital self-service to meaningfully transform customer servicing experiences and deliver measurable improvements in customer and operational outcomes. •In-depth knowledge of modern customer service technology ecosystems, including CRM and case management platforms, knowledge management systems, AI-powered servicing solutions, automation, and integrations between customer support tools. •Demonstrated ability to use data and member insights to identify friction, prioritize investments, measure impact, and continuously improve end-to-end servicing journeys. •Exceptional cross-functional leadership and stakeholder management skills, with the ability to influence technical and non-technical teams and connect technology investments to member and business outcomes. •Comfort operating at both strategic and executional levels in an ambiguous, rapidly evolving environment, with curiosity and fluency around emerging AI capabilities and their application to customer experience. •Strong commitment to embracing and leveraging AI tools in day-to-day tasks, ensuring AI-assisted work aligns with the same high-quality standards as personal contributions. •Interested in the role, but don’t meet every qualification? We encourage you to still apply! At WHOOP, we believe there is much more to a candidate than what is written on paper, and we value character as much as experience. As we continue to build a diverse and inclusive environment, we encourage anyone who is interested in this role to apply. Interested candidates, please apply directly through the job posting on company's career page or try via AI auto apply on this platform. Don't miss this opportunity to join a forward-thinking team!