User Experience Manager

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 looking for a hands-on Principal UX Manager to lead UX design across our web, mobile, agent, and service experiences. You'll set a UX vision and deliver it through iterative, measurable improvements, while leading a team through the most significant change the design discipline has seen in a generation. If you lead by example, are energized by AI rather than threatened by it, and want to build how UX works next, we want to hear from you.

What You Will Do

• 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, and prioritize against business metrics.
• Simplify complex insurance workflows (quoting, claims, servicing) into intuitive journeys with measurable ease-of-use gains.
• Plan and run user research, usability testing, and experimentation (A/B tests on CTAs, layouts, flows), and turn findings into action.
• Partner daily with Product Owners, BI Analysts, and Engineering on the Digital Experience Team to turn business goals into shipped experiences.
• Evolve and govern our design system across web and native mobile, including accessibility standards.
• Communicate design rationale clearly to stakeholders at every level.

AI-Driven UX: What We Expect

AI is fundamentally changing how design gets made and shipped, and this role leads that change on our team. You will:

• Use AI tools to turn designs into working code: generating production-quality front-end components and interactive prototypes from designs, and closing the gap between design intent and what ships.
• Use AI to connect our design system to the codebase, keeping tokens, components, and documentation in sync between design tools and code, and treating the coded system as the source of truth.
• Apply AI across the design workflow, including research synthesis, rapid concepting, content, prototyping, and accessibility review, while holding a high bar for quality and judgment.
• Redefine team workflows and roles as AI shifts the designer's work toward problem framing, systems thinking, and validation, and coach the team through that shift.
• Design AI-powered customer and agent experiences, such as chat, assistants, and AI-driven servicing, with an eye to trust, transparency, and regulatory expectations.
• Stay current on emerging AI design and development tools, evaluate them pragmatically, and bring the ones that work into practice.
• We are looking for someone who sees AI as core to the future of UX and is actively adopting it now. Candidates should be prepared to show real examples.

Required Qualifications

• Experience managing UX designers, with a portfolio showing web and mobile work and measurable outcomes.
• Demonstrated hands-on use of AI tools in design and design-to-code workflows (e.g., AI coding assistants, AI features in design tools, design-token pipelines).
• Deep expertise in user-centered design, design thinking, research, and usability testing.
• Experience building or evolving a design system in partnership with engineering.
• Strong business acumen and the ability to connect UX work to metrics such as conversion, close rate, digital adoption, and call deflection.
• Excellent communication and stakeholder management skills.
• A Bachelor's degree in Design, HCI, or a related field, or equivalent experience.

Preferred

• Insurance or financial services experience.
• Accessibility (WCAG) expertise for web and native apps.

Perks and Benefits:

• 4 weeks accrued paid time off + 9 paid national holidays per year
• Free onsite gym at our Boston Location
• Tuition Reimbursement
• Low cost and excellent coverage health insurance options that start on Day 1 (medical, dental, vision)
• Robust health and wellness program and fitness reimbursements
• Auto and home insurance discounts
• Matching gift opportunities
• Annual 401(k) Employer Contribution (up to 7.5% of your base salary)
• Various Paid Family leave options including Paid Parental Leave
• Resources to promote Professional Development (LinkedIn Learning and licensure assistance)
• Convenient location directly across from South Station and Pre-Tax Commuter Benefits

Salary Range:

$149,500 - $195,500 annual base salary + annual performance bonus. Actual compensation will vary based on multiple factors, including employee knowledge and experience, role scope, business needs, geographical location, and internal equity.

About the Company

The Plymouth Rock Company and its affiliated group of companies write and manage over $2.2 billion in personal and commercial auto and homeowner’s insurance throughout the Northeast and mid-Atlantic, where we have built an unparalleled reputation for service. We continuously invest in technology, our employees thrive in our empowering environment, and our customers are among the most loyal in the industry. The Plymouth Rock group of companies employs more than 2,000 people and is headquartered in Boston, Massachusetts. Plymouth Rock Assurance Corporation holds an A.M. Best rating of “A-/Excellent”.