Think about your last hotel stay. Did you skip the front desk line with mobile check-in? Message the staff for extra pillows? Order a late-night snack with a tap on your phone? Then you’ve likely run into Canary in the wild.
Canary Technologies is the leading agentic AI platform for hotel and guest management, powering the digital infrastructure for more than 20,000 hotels in 125+ countries. The world's most renowned hospitality brands, including Marriott International, Four Seasons and Wyndham Hotels & Resorts, partner with us to increase revenue, improve operations and elevate the guest experience.
We’ve executed the largest deployment of autonomous AI systems in hospitality, building technology that fundamentally redefines how guests and hotels interact. It’s made us one of the top-funded hotel technology companies in the world, with nearly $200M raised to date.
Canary has been recognized as a 2024 and 2025 Deloitte Technology Fast 500™ company, Inc. 5000 fastest-growing company, and swept the 2026 HotelTechAwards, including Best Place to Work, #1 Guest Experience Platform, and the Hotelier’s Choice Award. We’re scaling our team to bring innovation to life faster than ever.
We're growing quickly, and we're looking for people who are passionate about their work, want to grow with us and are ready to take on more responsibility along the way. We value rigor and velocity in equal measure: high standards, fast pace, real ownership. If that's the environment you're looking for, this is the place for you.
Come join us! Let’s shape the future of hospitality together.
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.
What You’ll Do
- 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
What We’re Looking For
- 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)
Compensation
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 work hard to make Canary a fun, rewarding, and high-energy place to work. Here’s how we take care of our flock:
Time Off
- Unlimited PTO: Take the time you need to truly rest and recharge.
- Holidays + Canary Days: Standard holidays plus monthly company-wide days off for a guaranteed long weekend.
- Birthday Holiday: A dedicated day off to celebrate you!
Travel & Office Flexibility
- Office Exchange: A travel stipend to visit the team in person at our SF, NY, or Dallas hubs.
- Canary Hotel Experience: Staying at a Canary hotel? We’ve got you covered with a credit toward your stay.
- Preferred Hotels Discount: Enjoy a minimum 30% off the best available rate at select partner hotels globally.
Growth & Community
- Self Improvement Club: A monthly budget to help you smash your personal goals.
- Professional Development: Level up your career with a dedicated learning stipend to fuel your skills and cross-functional connection.
- Referral Program: Help us grow the flock and score a cash bonus for successful hires.
Skills Required
- 8+ years in Product Design
- 3+ years leading teams directly
- Portfolio demonstrating end-to-end systems thinking and shipped work at scale across web and mobile
- Proven ability to recruit, develop, and retain diverse design talent; strength in feedback, coaching, and org-building
- Fluency in design systems, accessibility, UX research methods, and experimentation
- Hands-on experience with Figma, design tokens, and detailed specs
- Strong partnership skills with Product and Engineering; comfortable with ambiguity and enterprise constraints
- Experience designing for AI agents or autonomous interfaces
- Experience operating in B2B or B2B2C SaaS
- Familiarity with analytics tools
What We Do
Canary Technologies is a leader in hospitality technology that provides hoteliers with easy, intuitive, and secure solutions to help hotels provide an ideal guest experience.
