Director, Enablement Excellence- Member Services

Whoop•Boston, MA

10d

About The Position

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 of Enablement Excellence within our Membership Services (MS) team to lead the strategy and execution of the programs that enable best-in-class support for our members in pursuit of our Membership Services vision: We empower every member to perform every day. This leader will build and own the Enablement Excellence function for Membership Services - establishing the standards, systems, and programs that elevate MS performance, readiness, and consistency across every human and AI touchpoint.

Requirements

10+ years of experience in customer support, knowledge management, learning & development, or quality operations, including 5+ years of people leadership in a fast-paced, high-growth environment.
Proven track record of building and scaling knowledge, training, or quality programs that leverage both human expertise and AI-enabled technologies.
Experience leading multidisciplinary teams and managing senior-level talent across multiple functions or domains.
Deep understanding of customer service principles, instructional design, adult learning theory, and quality assurance methodologies.
Exceptional communication and stakeholder management skills with a strong ability to influence across all levels of the organization.
Comfort with ambiguity and a bias toward action—able to operate strategically while being hands-on where needed.
Experience working with tools such as LMSs, knowledge bases, automated QA platforms, or AI-powered coaching systems.
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.

Nice To Haves

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.

Responsibilities

Lead and develop the strategy and roadmap across a high-performing Enablement Excellence organization composed of Knowledge & Content, Learning & Training, and Quality leaders, fostering a unified culture of excellence, innovation, and continuous improvement within MS.
Oversee the teams responsible for creating, managing, and curating knowledge content for internal tools (including AI servicing solutions), ensuring accuracy, clarity, and accessibility for both members and MSRs to improve KPIs like member sentiment and first contact resolution.
Drive the design and delivery of scalable, AI-enhanced training programs - from onboarding new hires to preparing teams for new product launches and developing future leaders.
Lead the transformation of WHOOP’s quality program through the adoption of automated quality management and AI-driven coaching tools, fostering a culture of performance, coaching, and continuous improvement.
Own the strategy and optimization of the tools and systems that power Membership Services, ensuring seamless performance and alignment with business goals.
Serve as the Directly Responsible Individual (DRI) for the WHOOP AI support agent, overseeing its performance, accuracy, training data, content alignment, and ongoing optimization to ensure AI-driven support consistently reflects WHOOP standards for quality, clarity, and member empowerment.
Collaborate cross-functionally with Product, Engineering, AI, and Operations teams to ensure seamless integration of knowledge and training systems with evolving support technologies.
Develop and mentor a team of senior leaders while fostering a high-performance, mission-driven culture aligned with the WHOOP core values and commitment to member experience.