Head of Product Design

About Us

Canary Technologies is changing the game for hotels with modern software powered by Canary's hospitality-specific AI platform.

Canary is utilized by 20,000+ hoteliers in 100+ countries to equip hoteliers with the technology they need to work smarter and wow their guests. Major hotel brands such as Wyndham, Marriott, IHG, Four Seasons, Rosewood, and Best Western trust Canary to deliver results.

Canary was named a 2024 Deloitte Technology Fast 500™ company, a Most Innovative Company by Fast Company and a Hotel Tech Report  Best Place to Work — and is backed by top Silicon Valley investors like Y Combinator, F-Prime, Brighton Park Capital and Insight Partners.

Canary Technologies is hiring a Head of Product Design to own the design system, information hierarchy, and interaction principles that govern every surface of Canary's platform — for human users and AI agents alike.

Most design system roles are about consistency for humans. This one is about building the design language that AI agents obey. You're not just making a dashboard pretty — you're defining the rules of interaction for a platform where AI is increasingly the operator. That's a new kind of design leadership, and we want someone who sees it that way.

Canary's product surface is expanding fast across checkin, messaging, upsells, voice, and more. We need someone obsessive about consistency, hierarchy, and systematic design who can establish principles that scale — not just across screens, but across a future where AI agents are primary users of our interfaces. The design system you build won't just guide human designers; it will be the contract that AI follows.

• 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

• 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.
• You are 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)

Target cash compensation ranges from $250,000-$290,000
, including a fixed annual salary and a performance-based bonus paid quarterly.
This role also includes a stock option grant, subject to board approval.
Actual compensation will be commensurate with the candidate's skill level, experience, and specific work location.

We also work hard to ensure Canary is a fun and exciting place to work! Here are some of the additional benefits:

Canary Days: As a company we want to ensure that the team has time to recharge. Each month we…