Senior Director, Support (Member Care & Advocacy)

Headspace•San Francisco, CA

12d•$185,000 - $230,000•Hybrid

About The Position

About the Senior Director, Support at Headspace: 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. This is a rare opportunity to lead the support engine for a world-class brand that has already touched over 100 million lives globally. 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.

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.
Strong financial and analytical acumen, with experience in forecasting, budgeting and using data to guide strategic and operational decisions.
Passion for helping others and delivering exceptional, human-centered experiences.
Strategic systems thinker who connects micro-level member insights to macro business outcomes and influences cross-functional partners through clear, data-informed storytelling.
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).

Nice To Haves

Leadership roles in consumer technology, healthcare, or wellness industries.
Proven experience scaling operations through automation and partner ecosystems.
Success driving change and cultural transformation during organizational transitions or integrations.

Responsibilities

Leadership & Strategy 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 lead the operational model for the Member Care & Advocacy (MCA) organization, aligning team structure, staffing ratios, partner resourcing, and financial planning to ensure efficiency, scalability and consistent service levels.
In partnership with senior leaders, position MCA as a strategic driver of product, experience, and growth.
Operational Excellence & Analytical Rigor 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.
Culture & Team Building 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.
Cross-Functional Collaboration 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.
Innovation & AI Enablement 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.