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Underwriting Supervisor

Plymouth Rock Assurance

Office

Boston, MA, United States

Full Time

 

We are seeking a dynamic and analytical leader to oversee the daily operations of our underwriting department. In this pivotal role, you will not only manage a team but also ensure strict adherence to underwriting and regulatory guidelines while upholding our company standards for quality, productivity, and timeliness.

 

Key Responsibilities:

  • Prioritize exceptional customer service by delivering efficient support to agents and policyholders.

  • Lead staff development initiatives to ensure team performance and growth.

  • Create, maintain, and interpret detailed performance reports to monitor departmental success.

  • Analyze data to identify trends and service issues and recommend effective corrective actions.

  • Implement workflows and procedures that enhance service delivery and operational efficiency.

Qualifications

  • Strong interpersonal and leadership skills, with a proven ability to motivate and inspire your team.

  • In-depth knowledge of Property & Casualty insurance, particularly homeowners insurance.

  • Proficient underwriting, policy service, and problem resolution skills.

  • Exceptional analytical skills, with a demonstrated ability to identify, analyze, and interpret data trends and key service issues, and recommend actionable solutions.

  • Capacity to evaluate complex information effectively and make informed decisions.

  • Bachelor’s Degree.

  • Minimum of 3 years of supervisory experience and 5 years of relevant experience in the Property & Casualty industry.

  • Direct experience in personal lines homeowners underwriting.

 

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

 

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”.

 

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Underwriting Supervisor

Office

Boston, MA, United States

Full Time

August 15, 2025

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Plymouth Rock Assurance

PlymouthRock