About League

Founded in 2014, and with a total funding currently at $220 million; League is a platform technology company powering next-generation healthcare consumer experiences. Payers, providers, consumer health partners and employers build on League’s platform to deliver high-engagement, personalized healthcare experiences consumers love. Millions of people use solutions powered by League to access, navigate and pay for care.

Position Summary:

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.

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.

What You'll Be Doing:

• 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.
• Security-Related Responsibilities:
• 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.

CANADA APPLICANTS ONLY: The Canada-specific compensation range below for this full-time position is exclusive of bonus, equity and benefits. This range reflects the minimum and maximum target for base salaries for the position across all Canadian locations. The salary range is intentional to account for the performance and career progressions a Leaguer will experience in the role throughout their time at League. Where in the band you may land is determined by job-related skills/experience. Your recruiter can share more about the specific salary range specific to your skills and experience during the hiring process.

Compensation range for Canada applicants only

$156,200 - $190,900 CAD

Our employees come from different backgrounds, and we celebrate those differences. We are looking for the best candidates for our open roles, but do not expect applicants to meet every qualification in order to be considered. If you are excited about what you could accomplish at League and believe you can add value to our team, we would love to hear from you.

We are committed to equal employment opportunity regardless of race, color, ancestry, religion, sex, national origin, sexual orientation, age, citizenship, marital status, disability, gender identity or Veteran status. If you are an individual in need of assistance at any time during our recruitment process, please contact us at recruitinginfo@league.com.

Our 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.

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Use of AI Notice
We are committed to ensuring fairness and transparency throughout our hiring process. League may use Artificial Intelligence (AI) tools to assist in the screening of applicants for this position.

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