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The Cypress Group

Director of User Experience

chicago, IL

Check who can apply and the requirements below before continuing.

About this opportunity

The Cypress Group lists this Director of User Experience opportunity in chicago, Illinois. Review the employer’s description below for duties, qualifications and application requirements.

Job description

We are looking for a Director of User Experience to lead and evolve our UX function across product design, research, and design systems. This is a high impact leadership role for someone who wants to do more than manage a design team. You will help define how UX operates across the organization, influence senior product and technology leaders, and play a major role in how AI is incorporated into the design and product development lifecycle. A key focus will be evolving the company's enterprise design system for an AI enabled future; creating the standards, components, specifications, and documentation that can support both traditional development teams and emerging agentic development workflows.

If the following job requirements and experience match your skills, please ensure you apply promptly.

What You Will Do:

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

Influence product direction and requirements early in the development lifecycle

Own design system governance, documentation, component standards, and adoption

Improve experiences involving complex workflows, large data sets, and sophisticated professional users

Define UX metrics around usability, accessibility, adoption, and product experience

Hire, mentor, and develop designers and researchers while building the long-term capabilities of the team

Stay close enough to the work to provide hands-on design direction on high-priority initiatives

Qualified Candidates Will Have:

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 and structured specifications can enable agentic or automated development

Experience establishing standards or guardrails around AI tooling

Strong executive communication and stakeholder management skills

Ability to operate effectively between design, product, engineering, and senior leadership

Experience designing products with complex workflows, significant data, or technically sophisticated users

Working understanding of modern front-end development and web architecture

Experience with accessibility and inclusive design

Financial services domain knowledge is highly preferred, particularly experience within capital markets, trading, fintech, banking, asset management, or other complex financial technology environments

This is an opportunity to shape the future of UX within a sophisticated, technology-focused organization. You will have meaningful ownership across UX strategy, AI adoption, design systems, team leadership, and product direction, with exposure to senior decision-makers. xzgxqkn

This role is on site 4 days a week.

Worksite address

chicago, IL, 60629, US

Who can apply

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