Director, UX Design (Benefit)

Location: Remote Hub or Portland ME
Team: WEX Benefits Experience Design
Reports to: VP, Head of Design

About WEX

At WEX, we believe great design can transform the way people connect with their benefits. Our Benefits Design team is on a mission to create intuitive, accessible, and meaningful experiences that help employees maximize the value of their benefits and empower employers to deliver impact at scale.

Your Role

As the Experience Design Lead for WEX Benefits, you will shape the long-term design vision, strategy, and operating model for one of WEX’s most impactful platforms. You will lead cross-functional teams, influence senior stakeholders, and advocate for design excellence that drives measurable outcomes.

This is not just a design leadership role—it’s a strategic one. You will guide your team through ambiguity, define new experience frontiers, and serve as a voice of design at the highest levels. You bring systems thinking, customer obsession, and the ability to move fluidly from vision to execution.

What You’ll Do

Lead Strategic Design Vision

• Define and evangelize a North Star for the end-to-end employee benefits experience across touchpoints, channels, and customer segments.
   

• Establish and operationalize experience principles and design quality standards that scale across the product ecosystem.
   

• Guide teams through ambiguous problem spaces with a hypothesis-led, insights-driven approach that surfaces unstated needs and unlocks innovation.
   

• Lead high-impact workshops, including C-suite and executive strategy sessions, to align business, product, and experience outcomes.
   

Drive Design Excellence and Execution

• Orchestrate experience design across multiple products, services, and user journeys, ensuring cohesion and elevating the overall ecosystem.
   

• Lead AI-first design practices that integrate machine learning, automation, and personalization into the benefits experience.
   

• Partner with engineering and enterprise architecture to ensure design is embedded in implementation decisions, from architecture to go-live.
   

• Champion inclusive and accessible design at every level, holding your teams to the highest standards of usability and compliance.
   

Inspire and Elevate Talent

• Lead and mentor a team of senior designers, experience strategists, and design managers—cultivating a high-performing, inclusive, and growth-oriented culture.
   

• Foster cross-pollination of ideas across product lines and functions, enabling your team to operate as strategic partners, not just service providers.
   

• Serve as an executive coach and thought partner, growing design leadership across the organization and contributing to enterprise-wide design maturity.
   

Influence Through Insight & Storytelling

• Translate complex ideas, data, and strategy into clear, compelling stories for executive audiences, including C-suite and board-level communication.
   

• Guide the creation of sophisticated experience maps, prototypes, and data visualizations that uncover opportunities and shape direction.
   

• Drive a culture of learning and experimentation by connecting prototyping with product strategy, customer risk, and go-to-market planning.
   

What We’re Looking For

Core Expertise

• Strategic Design Leadership: Experience defining and delivering design strategy at the organizational level across complex systems.
   

• End-to-End Experience Architecture: Ability to orchestrate cohesive experiences across journeys, platforms, and teams.
   

• Advanced Facilitation: Confident designing and leading executive workshops that shape product direction and resolve ambiguity.
   

• Systems Thinking & Problem Definition: Expert in framing and solving large-scale, ambiguous, and high-stakes challenges.
   

• Design for AI & Data: Ability to lead teams in designing intelligent, adaptive experiences that leverage data at scale.
   

• Executive Storytelling: Comfortable influencing at the highest levels with data-informed narratives that inspire action.
   

• Cross-Functional Influence: Proven ability to collaborate with product, engineering, operations, and strategy teams at scale.
   

Preferred Qualifications

• 10+ years in experience design, service design, or UX—spanning enterprise platforms or ecosystems
   

• 5+ years in a design leadership role with experience leading senior designers and influencing executive stakeholders
   

• Experience in benefits, HR tech, healthcare, or financial services a strong plus
   

• Deep understanding of accessibility standards and inclusive design practices (e.g., WCAG, ADA)
   

Why WEX

• A mission-driven culture focused on improving people’s lives through better design
   

• A design-led organization with influence across business strategy, technology, and customer experience
   

• The opportunity to lead with vision and drive outcomes that scale to millions of employees and employers