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"The details are not the details. They make the design."
— Charles Eames
Lead the design of AI-powered features focusing on Conversational AI and create conversation frameworks to ensure consistent and engaging AI interactions. Collaborate with cross-functional teams to align user needs with AI capabilities and advocate for ethical AI design.
Responsibilities
- Lead the design of AI-powered features with a focus on Conversational AI assistants, proactive recommendations, generative content tools, and adaptive learning flows
- Create conversation frameworks — tone, style, and response patterns — that ensure AI interactions are consistent, engaging, and trustworthy across products and channels (in-app, web, voice, SMS)
- Prototype rapidly to explore conversation flows, multi-turn interactions, and multi-modal outputs (text, voice, visual)
- Collaborate closely with product managers, engineers, data scientists, research and content strategists to align user needs with AI capabilities, from prompt design to model selection
- Define company-wide AI design principles and interaction patterns that can scale across multiple products and use cases
- Lead zero-to-one design explorations, shaping net-new interaction models grounded in research and usability testing
- Advocate for AI capabilities and influence technical direction
- Mentor designers on AI design best practices, conversational UX, and emerging interaction models
- Partner with research from concept through execution (e.g., uncovering user needs, measuring performance, etc.), to iteratively build League’s AI experiences and measure impact
- Advocate for ethical AI design, bias mitigation, and transparency in user-facing AI interactions
Requirements
- 7+ years in product design, with 2+ years designing Conversational AI or AI-driven product experiences
- Proven track record designing for chatbots, virtual assistants, or voice interfaces
- Deep understanding of conversational design principles, including multi-turn flows, error recovery, and adaptive responses
- Strong grasp of AI/LLM capabilities and limitations — prompt engineering, context windows, model configuration, and response optimization
- Ability to design for multi-modal experiences (voice, text, generative images, video)
- Portfolio showcasing real-world AI products with deep reasoning behind design decisions
Key Skills
- Experience in health tech or other regulated industries
- Familiarity with AI ethics, bias reduction, and trust frameworks
- Hands-on experience with tools like Voiceflow, Botmock, Dialogflow, LangChain, or Rasa
- Technical fluency to collaborate with engineers on AI integration and feasibility
About League Inc.
Founded in 2014, League is the leading healthcare consumer experience platform, reaching more than 40 million people around the world and delivering the highest level of personalization in the industry. Payers, providers, and consumer health partners build on League’s platform to deliver high-engagement healthcare solutions proven to improve health outcomes. League has raised $285 million in venture capital funding to date, powering the digital experiences for some of healthcare’s most trusted brands, including Highmark Health, Manulife, Medibank, and Shoppers Drug Mart.
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