Senior Conversation Designer (AI)

TL;DR

Senior Conversation Designer (AI): Defining conversational patterns and interaction models for intelligent assistants in design and engineering software with an accent on reasoning visibility, error recovery, and scalable dialogue architecture. Focus on bridging language design with product thinking to ensure trust and utility in high-stakes professional workflows.

Location: Must be based in Canada (Remote)

Salary: $94,000–$137,500 CAD

What you will do

• Design and refine conversational and agentic interaction patterns, including reasoning visibility and action controls (cancel, retry, undo).
• Define dialogue flows, conversation architecture, and turn-level interaction models to shape assistant responses and follow-ups.
• Establish and evolve the assistant’s voice, tone, and persona using system-level prompting behaviors.
• Design robust error handling, fallback, and recovery flows to maintain useful interactions during AI uncertainty.
• Collaborate with product, engineering, and AI research teams to integrate scalable conversational capabilities into real workflows.
• Define and track quality metrics such as task success and user trust to continuously improve the experience.

Requirements

• 4+ years of experience in conversation design, UX design, or related fields with a shipped portfolio.
• Proven experience designing AI or chatbot experiences, specifically handling edge cases and probabilistic model behaviors.
• Hands-on understanding of LLM capabilities, limitations, and failure modes.
• Experience with prompt design and system prompts as part of the interaction design practice.
• Proficiency in Figma and experience with prototyping tools.
• Must be based in Canada.

Nice to have

• Experience with multi-agent systems or AI governance frameworks.
• Experience working with shared design systems.

Culture & Benefits

• Competitive annual base salary, performance-based bonuses, and stock grants.
• Comprehensive health, dental, and wellness benefits.
• Flexible work arrangements depending on role and team needs.
• Opportunity to shape foundational AI interaction patterns used across multiple enterprise products.
• Exposure to cutting-edge LLM-based products and platform-scale design challenges.