Head of Product Design

Canary Technologies; New York (NY); On-site; USD 250,000 - 290,000; Full time

Benefits offered by this job

Company-wide days off

Self-Improvement Club funding

Professional Development budget

Travel reimbursement

Personal Travel Reimbursement

Job summary

A dynamic technology company in New York is seeking a Head of Design to lead the development of a unified design system that governs the interactions of both human users and AI agents. You will define the design principles and ensure consistency across all platforms while leading a talented design team. Strong candidates will have extensive experience in product design, particularly in the B2B SaaS space. The position offers a competitive salary of $250,000 – $290,000 annually, plus additional bonuses and benefits.

Qualifications

• 8+ years in Product Design with 3+ years leading teams directly.
• Portfolio demonstrating end-to-end systems thinking and exceptional product craft.
• Fluency in design systems, accessibility, UX research methods, and experimentation.
• Proven ability to recruit, develop, and retain diverse design talent.

Responsibilities

• Define and enforce a unified design system across all product surfaces.
• Establish clear information hierarchy standards.
• Audit existing surfaces ruthlessly and drive convergence toward a coherent system.
• Think deeply about how AI agents interact with the UI, designing accordingly.

Skills

Product Design

Team Leadership

Design Systems

User Experience Design

B2B SaaS Experience

Collaboration with Engineering

UX Research Methods

Tools

Figma

Job description

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 check‑in, 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)

Compensation

$250,000 – $290,000 a year, including 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.

Benefits

• Canary Days: 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 can visit our offices across New York, San Francisco, or Dallas when they choose, and are provided a travel stipend for doing so.
• 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. 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.