UnderwriterPlymouth Rock Assurance

In this position, the Underwriter will be responsible for analyzing and interpreting insured and agency data, evaluating risk, and executing underwriting strategies to identify and address rate evasion, premium leakage, and potential exposure. This role will work collaboratively across the organization, partnering with Claims, Sales, Product, and Customer Care, as well as directly with insureds and agency partners, to investigate findings, resolve discrepancies, and ensure compliance with underwriting guidelines and state regulations.

The Underwriter will exercise sound underwriting judgment, identify opportunities to improve risk selection and premium accuracy, and drive measurable business results while maintaining the highest standards of customer experience and brand representation. The primary focus will be New Hampshire, with responsibilities that may extend across New England and New York.

To support the needs of the organization and the clients we serve, the Underwriter may also be asked to assist with Customer Care inquiries, endorsement processing, quoting, and other activities that contribute to the organization's overall success.

Essential Functions & Responsibilities

• Develop and maintain a strong understanding of state regulatory requirements, company products, underwriting guidelines, and underwriting philosophy.
• Evaluate insured and agency analytics to identify trends, assess risk, detect rate evasion, and recommend appropriate underwriting actions.
• Independently manage and execute a repeatable Rate Pursuit analytical process to evaluate policyholder and agency activity, identify premium discrepancies, and ensure accurate premium collection.
• Exercise sound underwriting judgment when reviewing risks, investigating discrepancies, evaluating referrals, and determining appropriate actions in accordance with company guidelines and regulatory requirements.
• Identify opportunities to improve underwriting results, strengthen risk selection, reduce premium leakage, and maximize premium collection.
• Manage multiple Rate Pursuit, new business, and renewal initiatives, including home inspections, new business policy reviews, umbrella renewal questionnaires, driver discovery, questionable risk referrals, and garaging analysis.
• Partner closely with Claims to evaluate loss trends, identify emerging risk exposures, and implement appropriate underwriting actions.
• Collaborate with Sales, Product, Customer Care, and agency partners to resolve underwriting issues, communicate findings, and support sound business decisions.
• Serve as a subject matter resource for underwriting guidelines, regulatory requirements, and established department practices.
• Support the development, maintenance, and documentation of underwriting procedures, ensuring consistency and compliance.
• Identify and recommend process improvements that enhance efficiency, accuracy, profitability, and the customer experience.
• Prepare and deliver timely, accurate progress reports, analytical findings, and monthly business results.
• Address escalated issues, complaints, questions, and inquiries professionally, using sound judgment and a customer-focused approach.
• Maintain a high standard of accountability, organization, and follow-through while managing multiple priorities and projects.
• Participate in special projects and other assignments as needed.
• Travel as required.

Qualifications & Education

• Minimum of 3 years of relevant underwriting, insurance analytics, risk assessment, or property and casualty insurance experience preferred.
• Experience analyzing and interpreting qualitative and quantitative data to support business decisions and risk evaluation.
• Demonstrated ability to assess risk, identify trends, investigate discrepancies, and make sound, well-supported underwriting recommendations.
• Strong knowledge of personal lines insurance, underwriting principles, and customer service practices.
• Personal Lines Auto, Home and Umbrella insurance experience preferred.
• Property and Casualty (P&C) license preferred.
• Exceptional analytical, critical-thinking, problem-solving, and decision-making skills.
• Excellent organizational, time-management, and communication skills, with the ability to manage multiple priorities and deadlines.
• Strong written and verbal communication skills, including the ability to explain underwriting decisions and findings to internal stakeholders, insureds, and agency partners.
• Proficiency in Microsoft Office, particularly Excel, with the ability to analyze data and communicate meaningful business insights.
• Ability to collaborate effectively across departments while working independently and taking ownership of assigned responsibilities.
• Commitment to process improvement, operational excellence, regulatory compliance, and delivering a high-quality customer experience.

Perks & 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: $60,000 - $82,500 a year. 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 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 1,900 people and is headquartered in Boston, Massachusetts. Plymouth Rock Assurance Corporation holds an A.M. Best rating of “A-/Excellent”.