Canary Technologies Corp
Head of Design
TLDR
Lead the development of a unique design system that empowers both human users and AI agents, ensuring a coherent interaction design across all product surfaces.
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 HotelTechReport Best Place to Work — and is backed by top Silicon Valley investors like Y Combinator, F-Prime, Brighton Park Capital and Insight Partners.
Join us in shaping the future of hospitality!
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.
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)
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 provide company wide days off to ensure there is at least one extended weekend or day off.
Self Improvement Club: We meet each month and share our personal goals for the month. Each individual is provided a budget towards any purchases that help us achieve these goals.
Professional Development Chats: We provide budget to help drive cross functional professional development conversations across the organization.
Travel Reimbursement: Team members are able to visit our offices across New York, San Francisco or Dallas when they choose, and are provided a travel stipend for doing so. Spend time working with the team in their office, and use the rest of your time exploring a new city!
Personal Travel Reimbursement: If you stay at a hotel that Canary works with, we provide a credit towards your stay.
Canary Technologies is an equal opportunity employer. We recruit, employ, train, compensate and promote talent regardless of race, religion, ethnicity, national origin, citizenship, gender, gender identity, sexual orientation, age, veteran status, disability, genetic information or any other protected characteristic.
Benefits
Self Improvement Club
Each individual is provided a budget towards any purchases that help us achieve these goals.
Personal Travel Reimbursement
If you stay at a hotel that Canary works with, we provide a credit towards your stay.
Canary Days
Each month we provide company wide days off to ensure there is at least one extended weekend or day off.
Canary Technologies builds innovative software for the hospitality industry, focused on enhancing guest experiences and streamlining hotel operations. Serving over 20,000 hoteliers across 100+ countries, their AI-powered platform equips major hotel brands with the tools to drive efficiency and elevate service standards.
- Employees
- 11-50 employees
- Industry
- Internet Software & Services
- Total raised
- $47M raised
Head of Human Resources