Head of 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 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!

About the Role

Canary Technologies is transforming how hotels operate and how guests experience their stay. As Head of Design, you will set a compelling multi‑year design vision and turn bold ideas into durable outcomes that customers feel and the business can measure. You’ll operate at the intersection of strategy and execution: creating clarity from ambiguity, rallying cross‑functional teams, and holding a high bar for craft, accessibility, and reliability. You will treat our design portfolio like a business by owning the KPIs, making focused bets, and iterating quickly based on customer truth and data. If you love raising the bar, inspiring teams, and shipping work that changes trajectories, this role is for you.

• Own the end-to-end design strategy across product surfaces spanning Arrivals & Departures, Guest Communications, Payments, and Mobile.
• Build, mentor, and manage a high-performing team of designers and researchers. Establish clear career paths and a strong design culture.
• Define and evolve Canary’s design system and component libraries across web and mobile. Ensure consistency, quality, and velocity.
• Partner with PM and Eng leads to shape problem definition, roadmap, and scoping for initiatives. Drive clarity and outcomes.
• Raise quality through strong critique, design reviews, and mechanisms for usability, accessibility, and brand expression.
• Lead research and discovery to deeply understand guest, staff, and enterprise stakeholder needs, translating insights into clear product decisions.
• Collaborate with Enterprise and Customer Success teams to support chain-wide rollouts and brand standards for global hotel groups.
• Establish operational practices for design planning, capacity, and measurement. Instrument the experience to quantify impact.
• Represent Design in exec forums. Communicate strategy, tradeoffs, and results with clear narratives and artifacts.

• 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.
• 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.
• Fluency in design systems, accessibility, UX research methods, and experimentation. Familiarity with analytics tools.
• Excellent written and verbal communication. Able to align executives and cross-functional partners around crisp narratives and metrics.
• Bonus: Experience in hospitality, payments, messaging, or mobile SDKs. Global or multi-brand experience across EMEA/APAC.

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.