Head of Customer Success

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 seeking a Head of Customer Success to build, define, and scale our Customer Success function. This leader will establish the strategy, playbooks, and tools that drive engagement, retention, and growth across some of WHOOP’s largest and most strategic customers. This role sits within the Enterprise team and is responsible for driving long-term engagement, retention, and growth across large customers from multiple strategic verticals. You will need to work horizontally across sales, product, engineering, and finance to deliver successfully in this role. You will be responsible for ensuring customer satisfaction and renewal. 

This is not an entry level position. This is a high-impact, foundational role. You will work cross-functionally with Sales, Product, Engineering, and Finance to ensure WHOOP delivers transformative value to customers, while also shaping how the Enterprise business scales globally. 

The ideal candidate is both a strategic leader and hands-on operator - someone who can act as a player-coach today and build a world-class Customer Success organization for the future.

*This role is based in the WHOOP office located in Boston, MA. The successful candidate must be prepared to relocate if necessary to work out of the Boston, MA office.*

• Build and Lead the Function: Establish the vision, strategy, and operating model for Customer Success at WHOOP, including playbooks, processes, and tools that can scale across enterprise and public sector accounts.
• Customer Relationship Management: Directly own and nurture a portfolio of enterprise accounts as a founding player/coach, ensuring customers derive maximum value from WHOOP and remain long-term partners.
• Onboarding & Implementation: Design and deliver effective onboarding experiences—leading launches, training sessions, and workshops—while building repeatable frameworks for future team members to execute.
• Voice of the Customer: Serve as a senior advocate for customers within WHOOP. Capture and share feedback to influence product, marketing, and engineering priorities, ensuring our roadmap reflects enterprise needs.
• Engagement & Adoption: Create and execute strategies that drive user adoption, engagement, and satisfaction at scale, with clear ROI and measurable business impact for customers.
• Renewal & Growth: Oversee renewal cycles, proactively mitigate churn risk, and partner with Sales to identify and pursue expansion opportunities within key accounts.
• Customer Journey Optimization: Map and continuously refine the enterprise customer journey, addressing pain points and implementing scalable best practices to ensure consistent success outcomes.
• Data-Driven Insights: Develop and manage a framework for customer health metrics and usage analytics. Present actionable insights to both customer stakeholders and WHOOP leadership.
• Cross-Functional Collaboration: Partner closely with Sales, Account Management, Product, Engineering, and Finance to align on customer strategies that maximize retention, growth, and long-term partnerships.
• Team Development: As the function scales, recruit, mentor, and lead a high-performing Customer Success team, fostering a culture of accountability, innovation, and customer obsession.

• Bachelor's degree in Business Administration, Marketing, or a related field.
• A customer-first mindset with strong relationship-building skills and the ability to engage stakeholders from program managers to executives.
• 8+ years of experience in Customer Success within B2B or Public Sector SaaS or health/performance technology.
• A demonstrated track record of retaining and growing key accounts in one or more verticals relevant to our enterprise strategy
• A strong point of view on the right way to do customer success, including how to implement automation and AI tools to enhance outcomes
• Strong presentation and communication skills, capable of delivering impactful training and executive-level business reviews.
• Flexibility to work across industries—from athletics to corporate wellness to defense—and adapt success strategies accordingly.
• Strong analytical skills to track and manage the right KPIs and present to leadership
• A proactive, collaborative, and entrepreneurial spirit suited for a fast-paced, high-growth environment.
• Passion for health, fitness, and technology is a plus.

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 liability.