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).
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