Senior Director, Support (Member Care & Advocacy)

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.

What you will do:

• 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.

What you will bring:

Required Skills:

• 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).

Preferred Skills:

• 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.

Location:

We are currently hiring this role remotely in the US and Hybrid for San Francisco (SF) and Los Angeles (LA). Candidates must permanently reside in the US full-time.
For candidates with a primary residence in the greater SF and LA areas, this role will follow our hybrid model. You’ll work 3 days per week from our office, allowing for impactful in-office collaboration and connection, while enjoying the flexibility of remote work for the rest of the week. Your recruiter will share more details about our hybrid model.

Pay & Benefits:

The anticipated new hire base salary range for this full-time position is $185,000-$230,000 + equity + benefits.

Our salary ranges are based on the job, level, and location, and reflect the lowest to highest geographic markets where we are hiring for this role within the United States. Within this range, individual compensation is determined by a candidate’s location as well as a range of factors including but not limited to: unique relevant experience, job-related skills, and education or training.
Your recruiter will provide more details on the specific salary range for your location during the hiring process.

At Headspace, base salary is but one component of our Total Rewards package. We’re proud of our robust package inclusive of: base salary, stock awards, comprehensive healthcare coverage, monthly wellness stipend, retirement savings match, lifetime Headspace membership, generous parental leave, and more. Additional details about our Total Rewards package will be provided during the recruitment process.

About Headspace

Headspace exists to provide every person access to lifelong mental health support. We combine evidence-based content, clinical care, and innovative technology to help millions of members around the world get support that’s effective, personalized, and truly accessible whenever and wherever they need it.

At Headspace, our values aren’t just what we believe, they’re how we work, grow, and make an impact together. We live them daily: Make the Mission Matter, Iterate to Great, Own the Outcome, and Connect with Courage. These values shape our decisions, guide our collaborations, and define our culture. They’re our shared commitment to building a more connected, human-centered team—one that’s redefining how mental health care supports people today and for generations to come.

Why You’ll Love Working Here:

• A mission that matters—with impact you can see and feel
• A culture that’s collaborative, inclusive, and grounded in our values
• The chance to shape what mental health care looks like next
• Competitive pay and benefits that support your whole self

How we feel about Diversity, Equity, Inclusion and Belonging:

Headspace is committed to bringing together humans from different backgrounds and perspectives, providing employees with a safe and welcoming work environment free of discrimination and harassment. We strive to create a diverse & inclusive environment where everyone can thrive, feel a sense of belonging, and do impactful work together.

As an equal opportunity employer, we prohibit any unlawful discrimination against a job applicant on the basis of their race, color, religion, gender, gender identity, gender expression, sexual orientation, national origin, family or parental status, disability*, age, veteran status, or any other status protected by the laws or regulations in the locations where we operate. We respect the laws enforced by the EEOC and are dedicated to going above and beyond in fostering diversity across our workplace.

*Applicants with disabilities may be entitled to reasonable accommodation under the terms of the Americans with Disabilities Act and certain state or local laws. A reasonable accommodation is a change in the way things are normally done which will ensure an equal employment opportunity without imposing undue hardship on Headspace. Please inform our Talent team by filling out this form if you need any assistance completing any forms or to otherwise participate in the application or interview process.

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Headspace participates in the E-Verify Program.

Privacy Statement

All member records are protected according to ourPrivacy Policy. Further, while employees of Headspace (formerly Ginger) cannot access Headspace products/services, they will be offered benefits according to the company's benefit plan. To ensure we are adhering to best practice and ethical guidelines in the field of mental health, we take care to avoid dual relationships. A dual relationship occurs when a mental health care provider has a second, significantly different relationship with their client in addition to the traditional client-therapist relationship—including, for example, a managerial relationship.

As such, Headspace requests that individuals who have received coaching or clinical services at Headspace wait until their care with Headspace is complete before applying for a position. If someone with a Headspace account is hired for a position, please note their account will be deactivated and they will not be able to use Headspace services for the duration of their employment.

Further, if Headspace cannot find a role that fails to resolve an ethical issue associated with a dual relationship, Headspace may need to take steps to ensure ethical obligations are being adhered to, including a delayed start date or a potential leave of absence. Such steps would be taken to protect both the former member, as well as any relevant individuals from their care team, from impairment, risk of exploitation, or harm.

For how how we will use the personal information you provide as part of the application process, please see: https://www.headspace.com/applicant-notice