Skip to content
CV Rocket
Get started
How it worksThe enginePricingBlogContactSign in

Open nowPosted 22 days ago

UX Manager

Plymouth Rock Assurance Corporation79 open roles

Where
Boston, MA, USA
Get the CV for this job

From $25 per CV, paid once. No subscription.

Your applicationOpen nowUX ManagerPlymouth Rock Assurance Corporation · Boston, MA, USA

  1. YouYes, apply to this one.

  2. CV RocketCV written for this posting.

  3. 25 readersRecruiter, hiring manager, skeptic. Round after round.

  4. CV RocketApplied on Plymouth Rock Assurance Corporation's own form.

The reply lands in your private mailbox

3×more interviews than doing it yourself with ChatGPT.

The clock on this job

Early applications get read.

11.4% of postings close within 7 days. Measured by our own scanner across the market.

Share of postings closed within
  1. 2.0%1 day
  2. 4.2%3 days
  3. 11.4%7 days
  4. 17.5%14 days
  5. 34.2%30 days
  6. 43.5%60 days
This job: posted 22 days ago

The posting

UX Manager, Digital Experience

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.
  • Working knowledge of HTML/CSS/JavaScript, enough to review and refine AI-generated front-end code.
  • 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.
  • Agile delivery experience.
  • Accessibility (WCAG) expertise for web and native apps.
  • Experience designing conversational or chatbot experiences

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”.

#LI-DNI

From $25, paid onceGet the CV for this job

What happens when you press

One press. We do the rest.

  1. A CV for this posting

    Written against Plymouth Rock Assurance Corporation's own wording, from every piece of relevant proof in your profile.

  2. 25 readers review it

    Recruiter, hiring manager, skeptic and more read every draft, round after round. You get the best round.

    The review screen in CV Rocket: how each CV was read, round by round.

  3. We apply on Plymouth Rock Assurance Corporation's form

    Our application engine gets through the hardest forms there are. Where a question needs you, AI suggests the best answer. Don't want us applying from our IP addresses? Use our Chrome extension: we apply straight from your own browser.

    An application in CV Rocket: every answer filled in on the employer's form.

  4. Every reply, sorted

    Plymouth Rock Assurance Corporation's answer lands in your private mailbox, and we classify it on arrival: interview, question, rejection.

    The CV Rocket inbox: each employer reply classified as an interview, an action or a rejection.

  5. Reply with AI

    AI helps you write the email, checks it and sends it. We show you whether the recruiter read it.

  6. The interview in your calendar

    Full integration with your calendar. The invitation goes straight in.

    An interview invitation in the CV Rocket inbox, added to the candidate's calendar.
Get the CV for this job

From $25 per CV, paid once. No subscription.

Why it works

3×

more interviews than doing it yourself with ChatGPT.

ChatGPT writes a CV and never learns what happened to it. We see every reply. For each CV we know:

  • How it was written, and how the review scored it
  • When we applied, and how long after the posting went up
  • Which posting, which company, which city
  • Who got the interview, and who heard nothing

That is how we know which CVs get called.

Get the CV for this job

From $25 per CV, paid once. No subscription.

The numbers game

More applications. More interviews.

Every application goes out with its own CV, written for that posting and paid once. Send enough of them and the law of large numbers finds you the job.

Get the CV for this job
By hand5–10
With CV Rocket100
applications a day

Nearby

Live postings like this one

Same employer first, then the same role elsewhere.

Before you press

Straight answers

Get the CV for this job

From $25 per CV, paid once. No subscription.

What if my background isn't good enough?

We make the most of the background you have. The CV uses every piece of relevant proof your profile holds, and one of the 25 readers reads your whole profile and flags what the CV left out.

Do you really apply for me?

Yes, on the employer's own form, the hardest ones included. Where a question needs you, you answer it right there and AI suggests the best answer. Don't want us applying from our IP addresses? Use our Chrome extension: we apply straight from your own browser.

Is it a subscription?

No. You pay once per CV, from $25. Every application goes out with its own CV, written for that posting.

One job. One CV.
Paid once.

Pick the posting you want. We write for it, apply for you and catch the reply.

Get the CV for this job

From $25 per CV, paid once. No subscription.