Senior Underwriter

In this position, the Senior Underwriter will be responsible for independently interpreting insured and agency analytics, partnering collaboratively across the organization, and leading efforts to identify and address Rate Evasion. This role will assess complex risk exposures and work closely with Claims, Sales, Product, and Customer Care, as well as directly with insureds and agencies, to resolve findings and drive underwriting outcomes.

The Senior Underwriter will consistently represent the brand, deliver Six Sigma–aligned results, and maintain the highest level of customer experience. This role will be primarily focused on Massachusetts, with responsibilities that may extend across New England and New York. To meet the needs of the organization and the clients we serve, this role may also support Customer Care inquiries, endorsement processing, quoting, and other underwriting activities that contribute to organizational success.

• Serve as a subject matter expert on state regulatory requirements, company products, underwriting guidelines, and underwriting philosophy.
• Lead and support the documentation, maintenance, and enhancement of departmental procedures.
• Identify, recommend, and help implement process improvements to improve underwriting effectiveness and efficiency.
• Deliver timely, accurate progress reports and monthly business results.
• Lead and execute a repeatable Rate Pursuit analytical process evaluating insureds and agency performance.
• Continuously assess methods to maximize premium accuracy and collection while mitigating risk.
• Act as an escalation point for complex issues, complaints, questions, and inquiries, responding with professionalism and sound judgment.
• Execute and oversee multiple Rate Pursuit, New Business, and Renewal projects, including but not limited to home inspections, umbrella renewal questionnaires, driver discovery, questionable risk referrals, and garaging analysis.
• Partner closely with Claims to analyze trends and recommend appropriate underwriting actions.
• Mentor and provide guidance to less experienced underwriting staff as needed.
• Participate in special projects as assigned

• Proven experience analyzing and interpreting complex qualitative and quantitative data.
• Strong organizational, communication, and stakeholder management skills.
• Exceptional analytical, critical thinking, and problem-solving abilities.
• Advanced knowledge of customer care techniques and underwriting best practices.
• Excellent written and verbal communication skills.
• Ability to manage multiple priorities and work independently.
• Strong proficiency in Microsoft Office, with advanced Excel skills.
• 5+ years of relevant underwriting experience preferred.
• Personal Lines Auto and Home experience strongly preferred.
• P&C License preferred.

• 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 (Linked In Learning and licensure assistance)
• Convenient location directly across from South Station and Pre-Tax Commuter Benefits

The pay range for this position is $69,000 to $109,000 annually. Actual compensation will vary based on multiple factors, including employee knowledge and experience, role scope, business needs, geographical location, and internal equity.

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”.