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About the role
- Senior Director of Support at Headspace leading in-house and outsourced support organization. Focusing on member satisfaction and strategic growth through operational excellence.
Responsibilities
- Own and evolve Support strategy across Member Care, Product, and Provider Support, driving a clear bar for what great looks like.
- Lead and develop in-house and outsourced teams, fostering empowerment, accountability, and cost effective resourcing designed to scale.
- Design and operationalize an AI-empowered support ecosystem that drives proactive insights, operational excellence, and measurable member outcomes.
- In partnership with senior leaders, position MCA as a strategic driver of product, experience, and growth.
- Set and drive measurable performance metrics across SLAs, NPS, and quality by architecting systems, processes, and enablement that elevate member and agent outcomes.
- Design and lead the operational model for the Member Care & Advocacy (MCA) organization, aligning team structure, staffing ratios and partner resourcing to ensure consistent service levels, workforce stability and SLA achievement.
- Command operational scale across internal teams and partner networks, ensuring every channel operates with precision, consistency, and efficiency.
- Leverage Voice of the Member intelligence to uncover systemic issues, partner cross-functionally to address root causes, and drive measurable improvements to member and provider end to end experiences.
- Build a high-performing, compassionate team culture rooted in a growth mindset and accountability. This requires a hands-on leader with a passion for coaching and continuous learning.
- Champion a Member-First approach, embedding empathy and advocacy into every interaction.
- Coach and empower leaders to make real-time, values-aligned decisions that drive impact.
- Partner across Product, Engineering, Care, and Operations to enhance tools, processes, and issue resolution.
- Ensure the member voice directly informs product, operational, and business strategy.
- Build strong cross-functional alignment by translating front-line insights into shared priorities and action.
- Identify and scale automation and AI solutions that improve speed, quality, and personalization.
- Apply a product mindset to internal systems - designing scalable, data-informed workflows that continuously improve agent and member experiences.
- Foster continuous improvement (“iterate to great”) while ensuring technology amplifies empathy, not replaces it.
Requirements
- 8+ years in customer support, operations, or member experience leadership; 3+ years leading managers and cross-functional teams.
- Deep expertise in member care, process improvement, and support technology ecosystems (e.g., Zendesk, CRM, AI tooling).
- Proven success managing in-house and outsourced teams, including partner and AI-augmented workflows.
- Strong analytical, strategic, and communication skills — able to connect operational insights to business impact.
- Passion for helping others and delivering exceptional, human-centered experiences.
- Strategic systems thinker with the ability to connect micro-level member pain points to macro-level business outcomes.
- Demonstrated success scaling high-impact teams and operations through empowerment, technology, and data.
- Bachelor’s degree in Business, Psychology, Operations, or related field (advanced degree preferred).
Benefits
- stock awards
- comprehensive healthcare coverage
- monthly wellness stipend
- retirement savings match
- lifetime Headspace membership
- generous parental leave
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