Tech Stack
Job Description, Responsibilities & Requirements
About the Position
Head of Design
New York, NY
Product Design / Full Time / Hybrid
About Us
Canary Technologies is revolutionizing the hospitality industry with its modern software powered by an AI platform tailored for hotels.
Canary is trusted by over 20,000 hoteliers in 100+ countries to provide the technology needed to work smarter and delight guests. Major hotel brands such as Wyndham, Marriott, IHG, Four Seasons, Rosewood, and Best Western rely on Canary to deliver results.
Canary was recognized as a 2024 Deloitte Technology Fast 500™ company, a Most Innovative Company by Fast Company, and a HotelTechReport Best Place to Work. The company 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 seeking a Head of Design to lead the design system, information hierarchy, and interaction principles that govern every surface of Canary's platform-for both human users and AI agents.
This role is unique as it focuses on building a design language that AI agents follow. You will not only be making the dashboard visually appealing but also defining the rules of interaction for a platform where AI is increasingly the operator. This requires a new kind of design leadership, and we want someone who embraces this vision.
Canary's product surface is rapidly expanding across check-in, messaging, upsells, voice, and more. We need someone who is meticulous about consistency, hierarchy, and systematic design, capable of establishing principles that scale across screens and into a future where AI agents are primary users of our interfaces. The design system you build will guide human designers and serve as 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 that are 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 standards without human review.
- Audit existing surfaces rigorously 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.
Requirements
- 8+ years in Product Design with 3+ years leading teams directly. Experience operating in B2B or B2B2C SaaS is 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 organizational building.
- Strong partner to Product and Engineering. Comfortable in ambiguity, rapid iteration, and enterprise constraints.
- 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 Offer
- 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 a budget to help drive cross-functional professional development conversations across the organization.
- Travel Reimbursement: Team members can visit our offices across New York, San Francisco, or Dallas 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.
About the Company
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.
We may use artificial intelligence (AI) tools to support parts of the hiring process, such as reviewing applications, analyzing resumes, or assessing responses. These tools assist our recruitment team but do not replace human judgment. Final hiring decisions are ultimately made by humans. If you would like more information about how your data is processed, please contact us.