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Principal, AI Product Designer

1 year

In short

Lead the design of AI-powered healthcare products focusing on Conversational AI assistants and adaptive learning flows. Collaborate with cross-functional teams to create engaging AI interactions and mentor designers on AI best practices. Must have 7+ years in product design.

Where
Onsite ยท Canada โ€” Toronto
Pay
Not stated. Typically $150k - $200k USD
Level
Senior-level ยท Full-time
League
League
  • Hybrid
  • Series C

Builds a healthcare experience platform for health plans and health systems.

0 open roles ยท usually open about 4 weeks

Position Summary

  • 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.
  • Compliance with Information Security Policies
  • Ensure access management is performed in compliance with the employee's role and responsibilities
  • Responsibility and accountability for executing League's policies and procedures within the department/ team
  • Notification of HR, Legal, Compliance & Security of any incidents, breaches or policy violations

What You'll Bring

  • 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.

Nice-to-Have

  • 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.
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