Director, Enablement- Membership Services

Director, Member Enablement

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

WHOOP is hiring a Director, Member Enablement within our Membership Services (MS) team to lead the technology, AI, knowledge, and tooling strategy that powers a premium service experience for WHOOP members. This leader will transform how members receive support and how our internal teams deliver it—leveraging AI, automation, intuitive servicing journeys, and a modern technology stack to reduce member friction, improve resolution, and enable increasingly personalized and scalable service.

You will partner closely with Product, Business Technology, AI Software, and Operations to identify opportunities across the end-to-end servicing journey and translate them into technology and operational solutions that elevate the member experience.

• 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.

• 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.

• Proven track record of using technology, AI, automation, or digital self-service to meaningfully transform customer servicing experiences and deliver measurable improvements in customer and operational outcomes.

• Strong understanding 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.

• Experience translating customer and frontline servicing pain points into technology requirements, product roadmaps, workflows, and scalable solutions in partnership with Product and Engineering teams.

• 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.

WHOOP is an Equal Opportunity Employer and participates in E-verify to determine employment eligibility. It is unlawful in Massachusetts to require or administer a lie detector test as a condition of employment or continued employment. An employer who violates this law shall be subject to criminal penalties and civil…