Director of User Experience
cypress groupChicago, IL
Director of User Experience
cypress groupChicago, IL
3 days ago
Occupations
Web and Digital Interface DesignersDesigners, All OtherComputer and Information Systems ManagersAbout the role
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.
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 UXPartner 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.
This role is on site 4 days a week.
Matching similar jobs
JOB OVERVIEW
Experience level
Manager
Location
Chicago, IL
Occupation
Web and Digital Interface Designers
Industry
Software Publishers
Posted
3 days ago
Tired of running searches?
Rank the roles you'd take once, and matches like these arrive on their own.
CREATE PROFILE