Who you are

• This role is for a designer who thrives in ambiguity, blends deep craft with technical fluency, and can translate AI’s potential into tangible, impactful product experiences
• 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
• 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

What the job involves

• We’re building the next generation of intelligent, human-centered products that improve people’s health and well-being. As part of our AI strategy, we’re creating experiences that feel natural, trustworthy, and adaptive, with Conversational AI at the core
• We’re looking for a Principal Product Designer – AI to set the vision and design for how AI seamlessly integrates into our products. You’ll lead the creation of chat assistants, generative interfaces, and multi-modal AI interactions that adapt to user needs in real time
• 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

The application process

• Applying to a role you love can be exhausting, and understanding the next steps can feel vague and uncertain. You have done the hard part of submitting your application; let's do ours by sharing potential next steps
• You should receive a confirmation email after submitting your application
• A recruiter (not a computer) reviews all applications at League
• If we see alignment with League's needs, a recruiter will reach out to learn more about your goals. The recruiter will also share the team-specific interview process depending on the roles you are exploring
• The final step is an offer, which we hope you will accept!
• Prior to joining us, we conduct reference and background checks. Additional checks could be required for US Candidates, depending on the role you are exploring

Benefits

• Flexible medical and dental plans
• 401(k) and RRSP matching programs
• Health, lifestyle, learning and family spending accounts
• Employee stock option program (ESOP)
• Generous leaves (including parental and sabbatical)
• Flexible time off