Principal UX Leader: AI‑Driven Design & Systems

Plymouth Rock Assurance; Boston (MA); On-site; USD 149,000 - 196,000; Full time

Benefits offered by this job

4 weeks leave

Onsite gym Boston

Tuition reimbursement

Health insurance from Day 1

Wellness program funding

Insurance discounts

401(k) employer contribution

Paid family leave

Professional development resources

Pre-tax commuter benefits

Job summary

Plymouth Rock Assurance is seeking a hands-on Principal UX Manager to lead UX design across web, mobile, agent, and service experiences in Boston. You will set a UX vision, drive measurable improvements, and guide a team through a major evolution in the design discipline.

You will partner with Product Owners, BI Analysts, and Engineering to turn business goals into shipped, accessible experiences, while growing the design system and advocating AI-driven design across platforms.

Qualifications

• Experience managing UX designers.
• Hands-on use of AI tools in design and design-to-code pipelines.
• Deep expertise in user-centered design, design thinking, research, and usability testing.
• Experience building or evolving a design system with engineering.
• Ability to tie UX work to business metrics like conversion and adoption.

Responsibilities

• Lead, mentor, and grow a team of UX designers, setting standards for craft, research, and delivery.
• Own the UX vision and backlog for customer, agent, and claims digital experiences, prioritizing against business metrics.
• Simplify insurance workflows into intuitive journeys with measurable ease-of-use gains.
• Plan and run user research, usability testing, and experimentation; translate findings into action.
• Collaborate with Product Owners, BI Analysts, and Engineering to ship experiences.
• Evolve and govern the design system across web and native mobile, including accessibility standards.
• Communicate design rationale clearly to stakeholders at all levels.

Skills

UX leadership

AI in design

Design thinking

User research

Communication

Education

Bachelor's in Design/HCI

Tools

AI tooling

Design tokens

Job description

Plymouth Rock Assurance is seeking a hands-on Principal UX Manager to lead UX design across web, mobile, agent, and service experiences in Boston. You will set a UX vision, drive measurable improvements, and guide a team through a major evolution in the design discipline.

You will partner with Product Owners, BI Analysts, and Engineering to turn business goals into shipped, accessible experiences, while growing the design system and advocating AI-driven design across platforms.