Headspace

• Assist the Lead HR Generalist with employee and contractor lifecycle activities, including onboarding, contract extensions, offboarding, role changes, and internal transfers. • Coordinate and complete HR administrative tasks that support accurate, timely execution across the employee experience • Maintain employee records and ensure data integrity across People systems • Serve as the primary HR Operations point of contact supporting Provider Activation team for Care hiring • Serve as a first-line responder for People Ops inquiries, triaging questions and resolving routine requests with speed and accuracy • Escalate complex or sensitive issues to the Lead HR Generalist with appropriate context and documentation • Help maintain and improve self-service resources so employees can find answers quickly • Support the development and maintenance of SOPs, process guides, and internal documentation for employee & manager training of HR Operations processes • Assist in tracking and following up on open HR tasks, compliance items, and employee change workflows • Identify patterns in recurring questions or requests and surface them to the Lead Generalist to inform process improvements

• Provide high quality, innovative, tele-psychiatry to Headspace patients over a HIPAA-compliant video conferencing platform • Complete, sign and lock clinical case notes within 24 hours of session • Maintain your personalized database to record proof of licensure, license updates, expiration dates, personal information, etc. • Stay up to date with clinical leadership communication (checking and responding to emails in a timely fashion) • Work with a collaborative care team including mental health coaches, other therapists, psychiatric nurse practitioners, and external care providers

• Provide high quality, innovative, tele-therapy to Headspace patients over a HIPAA compliant video conferencing platform • Complete, sign and lock clinical case notes in EMR within 48 hours of session as part of the per-session reimbursement rate. • Maintain your personalized database to record proof of licensure, license updates, expiration dates, personal information, etc. • Keep your availability calendar up to date • Work with a collaborative care team including health coaches, other therapists, psychiatrists, and external care providers

• Provide high quality, innovative, tele-therapy to Headspace patients over a HIPAA compliant video conferencing platform • Complete, sign and lock clinical case notes in EMR within 48 hours of session as part of the per-session reimbursement rate. • Maintain your personalized database to record proof of licensure, license updates, expiration dates, personal information, etc. • Keep your availability calendar up to date • Work with a collaborative care team including health coaches, other therapists, psychiatrists, and external care providers

Director, AI Architect Location: San Francisco - Hybrid Job Description: About the Director, AI Architect at Headspace: At Headspace, our mission is to transform mental healthcare from an episodic need to an everyday care practice by offering an AI-powered, clinically safe, and personalized Mental Health Companion. AI is central to how we fulfill that mission at scale. As our Director, AI Architect, you will own the technical vision and execution of Headspace's AI-first service transformation, designing the systems, patterns, and practices that embed intelligence across every layer of our product and platform. Reporting directly to the Chief Product & Engineering Officer, you will operate at the intersection of applied research, ML science, and platform engineering. This is a rare opportunity to shape how a category-defining mental health company thinks about, builds with, and deploys AI, responsibly, scalably, and in ways that genuinely improve member outcomes. What you will do: - Define and lead Headspace's overarching AI architecture strategy, establishing the foundational patterns, platforms, and principles for an AI-first service transformation across our portfolio of streaming content, conversational AI, coaching, therapy and psychiatry services. - Architect end-to-end AI systems: including LLM-powered features, agentic workflows, retrieval-augmented generation (RAG), and real-time personalization, with a relentless focus on reliability, safety, and member impact. - Partner directly with the executive team, product leadership, and senior engineering stakeholders to align AI strategy with company goals, translating business opportunities into concrete technical roadmaps. - Author company-wide technical specs that establish AI design principles, evaluation frameworks, guardrails, and reusable platform components. - Drive responsible AI practices across the organization, including model evaluation, bias mitigation, explainability, data governance, and compliance with evolving regulatory standards relevant to health tech. - Lead the selection, evaluation, and integration of AI/ML infrastructure, including model providers, vector databases, orchestration frameworks, and MLOps tooling, balancing build vs. buy decisions with long-term strategic implications. - Collaborate with Data Science, ML Engineering, and Product teams to ensure AI systems are grounded in high-quality, privacy-preserving data pipelines and continuously improve through rigorous feedback loops. - Establish AI engineering standards and best practices across squads, from prompt engineering and context management to model versioning, observability, and production monitoring. - Mentor and elevate engineers, ML practitioners, and technical leads across the organization, helping teams build confidence and competency in applied AI development. - Serve as Headspace's internal and external thought leader on AI, representing the company's technical vision in recruiting, partnerships, and the broader industry. - Identify and evaluate emerging AI capabilities (reasoning models, multimodal systems, fine-tuning approaches) for near-term applicability to Headspace's roadmap. What you will bring: Required Skills: - 10+ years of software engineering experience, with at least 4 years focused on the design and delivery of production AI/ML systems at scale. - Deep expertise in modern AI architectures, including LLMs, RAG systems, embedding pipelines, agentic frameworks, and real-time inference, with hands-on experience moving these from prototype to production. - Proven ability to define AI strategy at an organizational level: translating ambiguous business challenges into technical roadmaps, influencing executive stakeholders, and driving alignment across cross-functional teams. - Strong command of responsible AI principles: safety, fairness, explainability, data privacy, and the unique ethical considerations of AI in health and wellness contexts. - Extensive experience with cloud-native AI infrastructure (AWS, GCP, or Azure), containerized deployment (Kubernetes), and MLOps practices including model serving, monitoring, and evaluation pipelines. - Demonstrated ability to evaluate and integrate third-party AI providers, orchestration frameworks (e.g., LangChain, LlamaIndex, or similar), and vector/embedding database systems. - Exceptional communication skills: you can articulate complex AI trade-offs clearly to both technical engineers and non-technical executives, and write specs that bring entire organizations along with you. - Ownership mindset: you are comfortable navigating ambiguity, making consequential architectural decisions with incomplete information, and taking accountability for outcomes across teams. Preferred Skills: - BS/MS/PhD in Computer Science, Machine Learning, or a related field, or equivalent practical experience. - Experience in digital health, wellness, or a similarly regulated consumer domain, with familiarity with HIPAA, data minimization practices, and the heightened standard of care for AI in sensitive user contexts. - Background in fine-tuning, RLHF, or domain-adapted model training for specialized consumer applications. - Experience with conversational AI, dialogue systems, or AI-powered coaching/companionship products. - Familiarity with Server-Driven UI (SDUI) and how AI-driven personalization integrates with dynamic, schema-based rendering across web and mobile clients. - Track record of building AI evaluation frameworks — including automated evals, red-teaming, and human-in-the-loop review pipelines — to maintain quality at scale. - Experience driving AI governance initiatives, including model cards, audit trails, and cross-functional risk review processes. Location: This is a hybrid role located in our San Francisco office, working 3 days per week from the office. Pay & Benefits: The anticipated new hire base salary range for this full-time position is $230,000-$287,500 + 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 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. Headspace participates in the E-Verify Program. Privacy Statement All member records are protected according to our Privacy 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 #LI-Hybrid

• Define the long-term technical vision for our cloud platform, advising leadership on architectural strategy, investment priorities, and systemic risk • Set organizational standards for cloud reliability, observability, and operational excellence, including SLO/SLI frameworks, incident management practices, and the platform tooling that underpins them • Serve as the senior solutions engineering authority for partner teams: translating cross-functional requirements into platform strategy and driving prioritization of developer experience investments • Own the developer experience roadmap, identifying and closing systemic gaps in self-service infrastructure, CI/CD workflows, and operational visibility across engineering • Proactively surface systemic risks in our AWS infrastructure, IaC practices, and delivery pipelines, and drive organizational action before issues become incidents • Translate complex infrastructure risk and platform strategy into clear, business-aligned narratives for Director-level and executive stakeholders to drive resourcing and prioritization decisions • Mentor Staff (T4) and Senior (T3) engineers and model the culture of engineering rigor, documentation, and cross-functional accountability expected across the organization

Senior Engineering Manager, Core Platform Location: Remote - United States Job Description: About the Senior Engineering Manager, Core Platform at Headspace: Headspace is on a mission to provide every person access to lifelong mental health support. We’re looking for a Senior Manager with deep technical expertise to lead our Core Platform team - delivering common capabilities across all of our Consumer and Business customers. As a Senior Manager of Core Platform at Headspace you will have meaningful opportunities to profoundly impact the future of mental health care for our 70 million users. The Core Platform team is the foundation every Headspace experience is built on—powering authentication, payments, entitlements, and shared services across our B2B and direct-to-consumer customers. Getting this right is essential to our mission and our ability to scale. We need an experienced leader who can drive the technical strategy, grow a high-performing engineering team, and ensure every product team at Headspace can build on a reliable, extensible platform. The right platform investments don't just reduce toil, they directly accelerate every product team's ability to ship, and this leader will be expected to quantify and communicate that impact. A big goal needs talented people, so come join us and give your day job a sense of purpose! What you will do: - Lead, attract, and grow stellar technical talent - Develop and drive strategic roadmaps for delivering rich, common capabilities to customers - Partner closely with product and engineering leaders across B2B and direct-to-consumer offerings to identify where common platform capabilities can replace bespoke solutions, reducing maintenance overhead, and accelerating feature delivery. Translate those opportunities into a platform roadmap with clear business impact. - Partner with Cloud/Ops, Security, and cross-functional engineering teams to ensure platform services meet availability, compliance, and operational standards, and proactively identify gaps before they become incidents - Distill complexity for technical and non-technical audiences - Partner with Principal Engineers to identify architectural gaps, evaluate build-vs-buy tradeoffs, and ensure platform technical direction is grounded in real engineering pain points across the org. - Effectively prioritize tradeoffs between reducing tech debt and developing new capabilities - Explore new technologies to support the future state of our business - Model tenacity and resilience in the day to day What you will bring: Required Skills: - 7+ years leading, building and developing top performing software development teams - Experience delivering software within a mobile development environment - Experience building and operating high-availability, distributed backend systems (auth, payments, identity, or similar) - Demonstrated ability to manage platform migrations or large-scale refactors without disrupting dependent teams - Track record of building or improving observability stacks (e.g., Datadog, OpenTelemetry, or similar) not just instrumenting systems but using data to drive engineering decisions - Track record of technical and functional stakeholder management, including an ability to distill complexity for both technical and non-technical audiences - Experience building and executing on cross-functional roadmaps, building OKRs and milestones - BS degree or higher in Computer Science, Computer Engineering, or other STEM major (Science, Technology, Engineering or Math) or equivalent experience Preferred Skills: - Experience as a technical leader with a track record of delivering results and making progress in a fast changing, ambiguous problem space - Ability to articulate, influence, and drive changes across multiple teams and levels of stakeholders - Background working in a health tech, fintech, or similarly regulated industry where compliance and security are first-class concerns Location: This role is open to candidates across the US, with preferred locations in San Francisco, CA (hybrid), New York City, NY (remote), and Seattle, WA (remote). Candidates must permanently reside in the US full-time. If your primary residence is in the greater San Francisco Bay Area, this role follows our hybrid model, with 3 days per week in office to support in-person collaboration. Your recruiter will share more details. Pay & Benefits: The anticipated new hire base salary range for this full-time position is $162,000-$225,000 + equity + benefits. For candidates based in San Francisco, New York City, or Seattle, a separate salary range of $207,000-$258,750 applies, consistent with our location-based compensation philosophy. 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. Headspace participates in the E-Verify Program. Privacy Statement All member records are protected according to our Privacy 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

Title: Principal Product Designer Location: Remote - United States; San Francisco - Hybrid Job Description: Headspace's mission is to create a world where mental health is never an obstacle. 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. Design is central to how that mission becomes real. We are seeking a Principal Product Designer to set the design direction for our most complex, high-stakes product surfaces, someone who operates at the intersection of strategic vision, deep craft, AI-forward thinking, and rigorous design research. You’ll be part of a collaborative team of designers and researchers, working closely with engineers, product managers, content creators, brand designers, and clinical experts to bring ideas to life. We’re looking for someone passionate about making a positive impact on both individuals and the world. If you’re into solving meaningful challenges, love behavioral design, and enjoy creating features that delight and support members, this could be the perfect fit. This role blends big-picture design thinking with hands-on creation. You’ll seamlessly move between talking to members to ideation and building intuitive flows and screens that make a real difference in the lives of people. What you will do: - Lead design strategy and execution for Headspace's most complex product areas , setting a high bar for interaction quality, visual craft, and member experience across consumer and B2B surfaces. - Define and drive design vision across multi-quarter workstreams, partnering closely with Product, Engineering, Research, and Clinical teams to ensure design thinking is embedded early and often in the product lifecycle. - Influence roadmap decisions and product strategy with evidence-based design rationale, representing the design perspective in cross-functional planning conversations. - Lead and conduct design research including generative studies, contextual inquiry, concept testing, and usability evaluations, to deeply understand member needs, behaviors, and mental models. - Partner with dedicated Research team members to define research agendas for your workstreams, and operate independently when research support is not available. - Apply behavioral design principles to create experiences that support habit formation, reduce friction, and drive meaningful engagement with mental health content and care. - Bring AI fluency to every stage of the design process , using AI-powered tools for prototyping, research synthesis, and rapid iteration to accelerate and elevate the quality of design work. - Mentor and elevate designers across levels , leading critique, sharing craft expertise in both design execution and research practice, and creating the conditions for others to do the best work of their careers. What you will bring: Required Skills: - 8+ years of experience designing thoughtful, human-centered products—ideally with exposure to emerging technologies or innovative problem spaces. - Exceptional visual design expertise with a strong portfolio showcasing high-impact, polished designs and a deep understanding of motion design principles. - Demonstrated AI fluency , actively uses AI tools (e.g. Claude, Figma Make, Cursor, generative prototyping tools, LLM-assisted research workflows) to accelerate and elevate design work, and can design AI-powered product experiences that feel natural, trustworthy, and human-centered. - Strong knowledge of iOS and Android patterns, behaviors, and interface design standards. - Proficiency in Figma and prototyping tools to create and communicate complex design ideas with clarity. - Experience designing interfaces for digital products, with a focus on crafting seamless, engaging, and accessible experiences. - A curious, strategic mindset with the ability to break down ambiguous challenges into actionable design solutions. - Demonstrated ability to drive cross-functional collaboration and clarify how design decisions align with broader team and company goals. - Proven ability to mentor, inspire, and cultivate a culture of design excellence while promoting a growth-oriented mindset. Preferred Skills: - 2+ years working in emerging technologies, AI-driven experiences, or other innovative product spaces. - Demonstrated design research competency , experience independently planning and executing generative and evaluative research methods (user interviews, usability testing, diary studies, concept testing) and translating findings into product-shaping insights is highly preferred. - Proven ability to lead engaging workshops and foster creativity across interdisciplinary teams. - Skilled in motion design and interaction design, creating dynamic and seamless user experiences. - Strong ability to explore, iterate, and refine ideas through prototyping, user testing, and experimentation. - Experience contributing to or working within design systems to ensure consistency and scalability. - Experience in healthcare or digital health is a plus, particularly where design work touched health behavior change, sensitive member journeys, or collaboration with clinical teams. Location: We are currently hiring this role remotely in the US and Hybrid for San Francisco (SF). Candidates must permanently reside in the US full-time. For candidates with a primary residence in the greater SF area, 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 $180,000-$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.

• Craft product requirements & experimentation plans for marketing measurement • Design and deliver the experimentation infrastructure required to measure the true causal impact of paid media spend on member acquisition, long-term retention, and sustainable LTV across all marketing channels • Author and maintain product specifications that translate complex measurement and experimentation requirements into actionable technical deliverables • Partner cross-functionally across Marketing, Growth, Engineering, and Data Science • Define and monitor the key metrics that connect platform-level measurement capabilities to business-level outcomes • Maintain and iterate on a structured learning system that synthesizes incrementality findings across channels • Partner with Legal and Privacy teams to ensure compliance with data privacy and consent requirements

• Interact closely with other cyber security architects, privacy officer, general counsel, engineering, and product management teams to ensure adequate security capabilities and controls are in place within the technology stack to mitigate security risks and meet the highest security and compliance requirements. • Work closely with prospects and the proposal managers to provide detailed responses to security assessment questionnaires. • Continuously research, design, advocate and recommend new security technologies, architectures, and products that will ensure meeting all compliance requirements. • Function as the go-to individual with in-depth understanding of all security and compliance related nuances within the Headspace Health stack. • Develop the ability to effectively navigate a highly complex environment to independently retrieve technical evidence for gaining assurance over the effectiveness of controls. • Serve as the subject matter expert who will actively guide the broader risk and compliance team on all security-related technical components within the environment. • Conduct ad-hoc security architecture/application reviews to assess new risks, keep abreast of latest cyber security technical risks, and foster a culture of continuous service improvement and service excellence.