Head of Design

New York, NYProduct /Full Time /HybridAbout UsCanary 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.ResponsibilitiesDefine and enforce a unified design system across all Canary product surfaces — components, spacing, typography, color, layout patterns, and page-level templatesEstablish clear information hierarchy standards so every page communicates priority, status, and action with zero ambiguityBuild design principles rigid enough to be programmatically enforced and flexible enough to serve diverse hospitality workflowsCreate specifications precise enough that AI coding agents can generate UI that meets your bar without human reviewAudit existing surfaces ruthlessly and drive convergence toward a single coherent systemPartner closely with engineering and product to make the design system the source of truth — not a side artifactThink deeply about how AI agents (voice, chat, autonomous) interact with and present Canary's UI, and design for that as a first-class use caseQualifications8+ 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 clarityFluency 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 UIMeticulous, opinionated, and able to hold the line on standards while moving fastComfortable being both hands-on (Figma, tokens, specs) and strategic (principles, governance, cross-pod alignment)CompensationTarget 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 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.We may use artificial intelligence (AI) tools to support parts of the hiring process, such as reviewing applications, analyzing resumes, or assessing responses and identifying potential inconsistencies or verification signals in application materials based on available information. 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.