Head of Product, Initiative

Sword Health is shifting healthcare from human‑first to AI‑first through its AI Care platform, making world‑class healthcare available anytime, anywhere, while significantly reducing costs for payers, self‑insured employers, national health systems, and other healthcare organizations. Sword began by reinventing pain care with AI at its core, and has since expanded into women’s health, movement health, and more recently mental health. Since 2020, more than 700,000 members across three continents have completed 10 million AI sessions, helping Sword's 1,000+ enterprise clients avoid over $1 billion in unnecessary healthcare costs.

Backed by 42 clinical studies and over 44 patents, Sword Health has raised more than $500 million from leading investors, including Khosla Ventures, General Catalyst, Transformation Capital, and Founders Fund. Learn more at

We are seeking a Head of Product to lead the development and market launch of an exciting new initiative. This is a high‑impact role where you will own the product strategy, drive execution from zero to one and beyond, and deliver an exceptional consumer experience that drives meaningful clinical outcomes and sustained member engagement. The Head of Product will work with the General Manager to help lead Sword's new initiative through an AI‑native experience.

By leveraging conversational AI, personalized care pathways, and intelligent support, they will help make AI care accessible to millions of members who face months‑long wait times for specialists and fragmented care experiences. This product will serve both direct‑to‑consumer and enterprise populations, requiring deep attention to growth, retention, and long‑term engagement across 4‑12 month care journeys. This role is critical to our mission.

You will shape how members experience AI care, determine which features drive sustained behavior change, and establish the product foundation to scale from launch to hundreds of thousands of members. You will work at the intersection of cutting‑edge AI capabilities and direct care delivery, balancing innovation velocity with clinical rigor and regulatory requirements.

• Product Strategy & Execution
• Own the product roadmap from pre‑launch through scale, balancing zero‑to‑one innovation with one‑to‑100 optimization
• Define and prioritize features that drive member engagement, retention, and clinical outcomes across 4‑12 month care journeys
• Establish clear product metrics, success criteria, and feedback loops to rapidly iterate and improve the member experience
• Partner with clinical, regulatory, and compliance teams to ensure product decisions meet healthcare standards while maintaining innovation velocity

• Design AI‑first product experiences that leverage agentic capabilities, conversational interfaces, and personalized recommendations to deliver exceptional consumer value
• Develop and implement evaluation frameworks (evals) to measure AI model performance, accuracy, safety, and member satisfaction
• Maintain deep understanding of available AI models (LLMs, fine‑tuning approaches) and make strategic decisions about which models to use for which use cases
• Collaborate with clinical, ML engineering and applied AI teams to ensure safety and quality and optimize model performance, latency, cost, and reliability in production
• Leverage AI tools throughout the product development lifecycle to accelerate research, prototyping, testing, and go‑to‑market preparation
• Stay current on AI capabilities and emerging techniques, continuously evaluating how new developments can enhance the member experience

• Build and execute strategies to drive member activation, and long‑term retention in both B2C and B2B2C contexts
• Design onboarding experiences, engagement loops, and re‑engagement strategies optimized for sustained behavior change
• Analyze member behavior, drop‑off points, and engagement patterns to identify opportunities for product improvement
• Partner with growth, marketing, and commercial teams to align product experience with go‑to‑market strategy
• Develop hypotheses and run experiments to continuously improve conversion, engagement, and…