Senior Director of Support, Headspace Health

• 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)

Desirable

• The Senior Director of Support (Member Care and Advocacy (MCA)) leads Headspace’s in-house and outsourced support organization — transforming it into a proactive, AI-enabled, and insights-driven capability that powers member satisfaction, provider enablement, and business growth
• You’ll be at the heart of an experience that doesn’t just service users — it helps shape how people engage with mental health, sleep, mindfulness, and wellbeing every day
• You’ll bring a members first mindset to make the mission matter, and set a clear bar for what great support looks like across all support touchpoints
• Balancing empathy with operational rigor and innovation, continuously improving workflows in the spirit of iterating to great, you’ll build scalable systems and highly personalized, human-centered experiences
• The Senior Director ensures MCA operates as a strategic engine — combining exceptional service, data-driven insights, and intelligent automation
• 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