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Posted 2 weeks ago

Director, AI Architect

at Headspace

Hybrid

Responsibilities

  • 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.
  • 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.
  • 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.
  • Identify and evaluate emerging AI capabilities (reasoning models, multimodal systems, fine-tuning approaches) for near-term applicability to Headspace's roadmap.
  • Track record of building AI evaluation frameworks — including automated evals, red-teaming, and human-in-the-loop review pipelines — to maintain quality at scale. •

Requirements

  • 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.
  • 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:
  • 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.
  • 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. 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.
  • 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.
  • Experience driving AI governance initiatives, including model cards, audit trails, and cross-functional risk review processes. Location:
  • We strive to create a diverse & inclusive environment where everyone can thrive, feel a sense of belonging, and do impactful work together.

Experience

  • 10+ years of software engineering experience, with at least 4 years focused on the design and delivery of production AI/ML systems at scale.

Benefits

  • Serve as Headspace's internal and external thought leader on AI, representing the company's technical vision in recruiting, partnerships, and the broader industry.
  • 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
  • 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.
  • 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.
  • The chance to shape what mental health care looks like next Competitive pay and
  • How we feel about Diversity, Equity, Inclusion and Belonging:
  • 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.

Contact

  • 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

Additional details

  • Ownership mindset: you are comfortable navigating ambiguity, making consequential architectural decisions with incomplete information, and taking accountability for outcomes across teams. Preferred Skills:
  • Headspace exists to provide every person access to lifelong mental health support.
  • 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.
  • A mission that matters—with impact you can see and feel
  • A culture that’s collaborative, inclusive, and grounded in our values
  • 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.
  • 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.

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