Director, Enablement Excellence- Member Services

Whoop; Boston (MA); On-site; USD 130,000 - 175,000; Full time

Benefits offered by this job

Equity package

Benefits

Competitive base salary

Job summary

WHOOP is seeking a Director of Enablement Excellence to lead Membership Services strategy, programs, and operations, elevating knowledge, training, and quality across AI-enabled support. The role builds standards, owns enablement systems, and mentors senior leaders to drive member-first outcomes.

The role collaborates with Product, Engineering, AI, and Operations to ensure seamless integration of training and knowledge platforms, scaling performance and readiness in a fast-growing company.

Qualifications

• 10+ years in customer support/knowledge management/learning & development/quality operations.
• 5+ years in people leadership in a fast-paced, high-growth environment.
• Experience building and scaling knowledge, training, or quality programs that leverage AI-enabled technologies.
• Experience leading multidisciplinary teams and managing senior-level talent across multiple functions or domains.

Responsibilities

• Lead strategy and roadmap for Enablement Excellence within Membership Services.
• Oversee content creation and curation for internal tools including AI servicing solutions.
• Design and deliver scalable, AI-enhanced training programs.
• Transform WHOOP’s quality program with automated QA and AI-driven coaching.
• Own strategies for tools and systems powering Membership Services.
• Oversee WHOOP AI support agent performance and alignment.
• Collaborate with Product, Engineering, AI, and Operations for integration.
• Develop and mentor senior leaders and foster mission-driven culture.

Skills

Customer support leadership

Knowledge management

Learning & development

Quality assurance

AI-enabled technologies

Stakeholder management

Strategic thinking

Tools

LMSs

Knowledge bases

Automated QA platforms

AI-powered coaching systems

Job description

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.

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.

Qualifications

• 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.

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 liability.

The WHOOP compensation philosophy is designed to attract, motivate, and retain exceptional talent by offering competitive base salaries, meaningful equity, and consistent pay practices that reflect our mission and core values.

At WHOOP, we view total compensation as the combination of base salary, equity, and benefits, with equity serving as a key differentiator that aligns our employees with the long-term success of the company and allows every member of our corporate team to own part of WHOOP and share in the company’s long-term growth and success.

The U.S. base salary range for this full-time position is $130,000 - $175,000. Salary ranges are determined by role, level, and location. Within each range, individual pay is based on factors such as job-related skills, experience, performance, and relevant education or training.

In addition to the base salary, the successful candidate will also receive benefits and a generous equity package.

These ranges may be modified in the future to reflect evolving market conditions and organizational needs. While most offers will typically fall toward the starting point of the range, total compensation will depend on the candidate’s specific qualifications, expertise, and alignment with the role’s requirements.