Head of User Experience & AI-Driven Design Systems

The Cypress Group

Chicago (IL)

On-site

USD 150,000 - 210,000

Full time

2 days ago

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Job summary

The Cypress Group seeks a Director of User Experience to lead UX across product design, research, and design systems. This executive role shapes how UX operates in the organization, guiding AI-enabled design and enterprise design system evolution.

You will mentor a global team, partner with senior leaders in Product, Engineering, and Technology, and establish standards, governance, and roadmaps that improve usability, accessibility, and product outcomes.

Qualifications

10+ years of UX, product design, or UX research experience.
3+ years leading designers, researchers, or UX teams.
Experience building, scaling, or evolving a UX organization.
Strong experience owning an enterprise design system.
Experience with AI-enabled design, development, or research workflows.
Understanding of how design systems enable agentic or automated development.

Responsibilities

Lead and develop a global team across UX design, research, and design systems.
Own the broader UX strategy, standards, and roadmap.
Define the approach to AI-assisted design, research, and product delivery.
Evolve an enterprise design system to support AI and agent-driven development workflows.
Establish standards and guardrails for how AI tools are used across UX.
Partner with senior leaders across Product, Engineering, Technology, and the business.