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About the Company

The Plymouth Rock Company and its affiliated group of companies write and manage over $2.4 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".

About the Role

The Customer Experience (CX) Program Director is responsible for leading the vision, strategy, and execution of customer insights initiatives across the organization. This role synthesizes data from multiple sources to drive actionable outcomes, foster a customer‑centric culture, and enhance customer value across the entire lifecycle. The role requires strong leadership, strategic thinking, and collaboration across cross‑functional teams without direct reporting authority.

Responsibilities

Lead and manage cross‑functional CX initiatives aligned with business goals.

Translate customer insights from voice analytics, automated QA, social media, and third‑party sources (e.g., J.D. Power) into strategic actions.

Conduct root cause and driver analysis, segmentation, and journey mapping to uncover friction points and improvement opportunities.

Design and execute surveys, usability testing, and qualitative research initiatives.

Establish a company‑wide customer success strategy through integrated processes, content, and data.

Develop and maintain a full customer lifecycle model to ensure measurable value realization at every stage.

Maintain repositories of insights, action libraries, trends, and customer data.

Serve as a subject matter expert in voice / text transcript analytics and optimize their use.

Create and evolve programs that drive customer lifetime value and deliver business impact.

Champion a continuous customer feedback loop across the organization; advocate for the voice of the customer and embed customer‑centric thinking in key decisions.

Design surveys and report on customer experience outcomes to leadership.

Qualifications

10+ years of experience in CX leadership roles.

Proven expertise in customer research, data analysis, and experience design.

Strong stakeholder influence, executive communication, and storytelling skills.

Demonstrated ability to lead cross‑functional projects and drive results without direct authority.

Experience in the Property & Casualty Insurance industry is preferred.

Bachelor's degree required; MBA or relevant advanced degree preferred.

Required Skills

CX strategy, research methods, stakeholder cadence, engagement, and executive communication.

Managing data, drawing conclusions, and sharing recommendations for buy in.

Survey and CX platforms, sampling logic, A / B testing, insights into new tools and capabilities.

Optimizes customer voice platforms.

Develop a deep understanding of Plymouth Rock customers.

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

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