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Canary TechnologiesCanary TechnologiesNew York, NY

Head of Design

Leads design for Canary's hospitality platform, owning the design system, information hierarchy, and interaction principles for human and AI agent users. Requires 8+ years in product design, 3+ years leading teams, and expertise in scalable B2B SaaS design systems.

250k – 290k
Hybrid8+ YOEProduct Design

About the role

Responsibilities

  • Define and enforce a unified design system across all Canary product surfaces — components, spacing, typography, color, layout patterns, and page-level templates
  • Establish clear information hierarchy standards so every page communicates priority, status, and action with zero ambiguity
  • Build design principles rigid enough to be programmatically enforced and flexible enough to serve diverse hospitality workflows
  • Create specifications precise enough that AI coding agents can generate UI that meets your bar without human review
  • Audit existing surfaces ruthlessly and drive convergence toward a single coherent system
  • Partner closely with engineering and product to make the design system the source of truth — not a side artifact
  • Think deeply about how AI agents (voice, chat, autonomous) interact with and present Canary's UI, and design for that as a first-class use case

Qualifications

  • 8+ years in Product Design with 3+ years leading teams directly. Experience operating in B2B or B2B2C SaaS preferred.
  • Portfolio demonstrating end-to-end systems thinking, exceptional product craft, and shipped work at scale across web and mobile is essential.
  • Proven ability to recruit, develop, and retain diverse design talent. Strength in feedback, coaching, and org-building.
  • Strong partner to Product and Engineering. Comfortable in ambiguity, rapid iteration, and enterprise constraints.
  • Inspired by companies like Rippling, Linear, or Stripe where systematic design creates product clarity
  • Fluency in design systems, accessibility, UX research methods, and experimentation. Familiarity with analytics tools.
  • Excited by the idea that your design system becomes the rulebook for AI agents building and operating UI
  • Meticulous, opinionated, and able to hold the line on standards while moving fast
  • Comfortable being both hands-on (Figma, tokens, specs) and strategic (principles, governance, cross-pod alignment)

Skills

FigmaDesign SystemsAccessibilityUx ResearchAnalytics ToolsTokensDesign TokensPrototypingInformation ArchitectureDesign Principles

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