Head of Design
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Overview
Schedule
Full-time
Career level
Executive
Remote
Option for remote
Compensation
$250,000-$290,000/year
Benefits
Paid Vacation
Career Development
Job Description
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 hiring a Head of 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.
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)
The expected total cash compensation range for this role is $250,000 - $290,000. This figure includes a competitive base salary and a performance-based bonus that is paid quarterly. This role may also include the opportunity to earn equity. Compensation is subject to standard withholding and applicable taxes. 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 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.
Automate your job search with Sonara.
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FAQs About Head of Design Jobs at Canary Technologies Corp
What is the work location for this position at Canary Technologies Corp?
This job at Canary Technologies Corp is located in New York, NY, according to the details provided by the employer. Some roles may also include multiple work locations depending on the requirement.
What pay range can candidates expect for this role at Canary Technologies Corp?
Candidates can expect a pay range of $250,000 and $290,000 per year.
What employment applies to this position at Canary Technologies Corp?
Canary Technologies Corp lists this role as a Full-time position.
What experience level is required for this role at Canary Technologies Corp?
Canary Technologies Corp is looking for a candidate with "Executive" experience level.
Does Canary Technologies Corp allow remote work for this role?
Yes, this position at Canary Technologies Corp supports remote work, giving candidates the flexibility to work outside the primary office location.
What benefits are offered by Canary Technologies Corp for this role?
Canary Technologies Corp offers following benefits: Paid Vacation and Career Development for this position. Actual benefits may vary depending on the employer's policies and employment terms.
What is the process to apply for this position at Canary Technologies Corp?
You can apply for this role at Canary Technologies Corp either through Sonara's automated application system, which helps you submit applications 10X faster with minimal effort, or by applying manually using the direct link on the job page.