Director, Enablement Excellence — AI-Driven 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

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.