Director, Enablement- Membership Services

Whoop
Boston
Workplace: OnsiteFull timeUSD 130,000 - 175,000 annuallyFunction: Executive & General ManagementExperience: 10+ yearsSkills: ["Cross-functional leadership","Stakeholder management","Strategic and executional thinking","Data-driven decision-making","Influence"]

Lead technology and AI enablement for Membership Services to deliver a premium, scalable member support experience. Own the roadmap for AI-powered member servicing, including strategy and optimization for the WHOOP AI support agent. Continuously improve the Membership Services technology ecosystem—tools, integrations, workflows, and automation—while defining knowledge and content strategy for both self-service and human+AI resolution. Partner cross-functionally to reduce friction and improve resolution efficiency using member and operational data.

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FursaFursa
Whoop
Whoop
2 days ago

Director, Enablement- Membership Services

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Last checked: 9 hours agoStatus: Live

Job Summary

Lead technology and AI enablement for Membership Services to deliver a premium, scalable member support experience. Own the roadmap for AI-powered member servicing, including strategy and optimization for the WHOOP AI support agent. Continuously improve the Membership Services technology ecosystem—tools, integrations, workflows, and automation—while defining knowledge and content strategy for both self-service and human+AI resolution. Partner cross-functionally to reduce friction and improve resolution efficiency using member and operational data.
Location: Boston
Workplace: Onsite
Employment Type: Full time
Job Function: Executive & General Management
Seniority: Director level

Key Responsibilities

  • •Define and lead the technology and AI enablement strategy for Membership Services, building a roadmap that improves servicing journeys and resolution efficiency.
  • •Serve as the DRI for AI-powered member servicing, owning the WHOOP AI support agent’s strategy, performance, accuracy, knowledge inputs, capabilities, and optimization.
  • •Own and continuously improve the Membership Services technology ecosystem, evaluating tools, platforms, integrations, workflows, and automation for MSRs and operations teams.
  • •Lead Knowledge & Content strategy for human and AI servicing to ensure accurate, structured, accessible knowledge that powers self-service, AI, and human support.
  • •Identify and eliminate friction across end-to-end member servicing journeys by using feedback and operational data, partnering cross-functionally on solutions that improve sentiment and reduce member effort.

Pay and Benefits

Salary: USD 130,000 - 175,000 annually
Equity and Bonus:Equity

Key Requirements

  • •10+ years of experience in customer experience, customer support technology, service operations, product operations, digital transformation, or related areas, including 5+ years of people leadership.
  • •Proven ability to use technology, AI, automation, and/or digital self-service to transform customer servicing and drive measurable improvements.
  • •Strong understanding of customer service technology ecosystems, including CRM/case management, knowledge management, AI-powered servicing, automation, and integrations.
  • •Ability to translate customer and frontline pain points into technology requirements, workflows, and scalable solutions with Product and Engineering teams.
  • •Use data and member insights to identify friction, prioritize investments, measure impact, and continuously improve end-to-end servicing journeys.
Experience:10+ yearsCustomer experienceCustomer support technologyService operationsDigital transformation
Skills:Cross-functional leadershipStakeholder managementStrategic and executional thinkingData-driven decision-makingInfluence
Tech Stack:AIAutomationDigital self-serviceCRMCase managementKnowledge management systemsIntegrations

Company Brief

Whoop
Whoop designs and sells a subscription-based wearable fitness tracker and analytics platform that monitors recovery, strain, and sleep to optimize athletic performance and daily health for consumers and professional athletes.
Industry: Wearables
Company Size: Large (251 to 1,000 employees)
Growth: Scaleup
Valuation: Unicorn (USD 1B+)
Funding: Series E+
Headquarters: Boston, United States
Founded: 2012
WebsiteLinkedIn