Plymouth Rock Assurance

Sr. Underwriter

Job Locations US-MA-Boston
Customer Service
Regular Part-Time

In this position, the Senior Underwriter will be responsible for interpreting insured and agency analytics, work collaboratively across the organization, executing and creating processes to identify and address Rate Evasion.  Identify potential areas of risk and working internally with Claims, Sales, Product and Customer Care and directly with insured and agencies to resolve findings.  Reviewing and evaluating Automobile new business applications, renewals and endorsements for completion, accuracy and compliance with underwriting guidelines.  Within company policy and guidelines, make underwriting decisions using appropriate tools and use independent judgement in accordance to given authority.  The ideal candidate will also provide underwriting support and direction to agencies to improve growth and profit objectives.  This will include conducting High Loss Ratio agency activities and execute agency audits.  Emphasis is placed on customer service, agency underwriting, and building relationships in support of corporate goals.    This role will be focused on Massachusetts and New York results with responsibilities that may extend across the enterprise 


To meet the needs of our organizations and the clients we serve, your role will be asked to support Customer Care inquiries, Endorsement processing, quoting and any other activities that will support the organizations success.



  • Become a knowledge resource and thought leader for state regulator requirements, the firm’s products and underwriting guidelines and philosophy.
  • Support the development of new employees and existing associates through coaching and training in accordance with department procedures.
  • Become subject matter experts and actively asses process improvement opportunities; follow and support the documentation and maintenance of department procedures.
  • Develop enhanced tracking and reporting capabilities while delivering timely and accurate progress reports and monthly business results as required.
  • Identify and execute repeatable Rate Pursuit analytical process to evaluate insured’s and our agency force.
  • Constantly and consistently evaluate methods that will enable the firm to maximize premium collection.
  • Be available and approachable and thoughtfully address escalated issues, complaints, questions and inquiries.
  • Conduct agency audits to ensure compliance with underwriting guidelines.
  • Leverage Marketing & Analytics/System generated reporting to identify, investigate and potentially audit agencies.
  • Execute multiple Rate Pursuit, New Business and Renewal projects. This may include new business policies review, umbrella renewal questionnaires, driver discovery, questionable risk referrals and garaging analysis.
  • Work closely with the Claims department to evaluate trends and take appropriate Underwriting action. Act as a resources and work collaboratively to improve Questionable Risk lifecycle results.
  • Special projects as assigned. In their absence, may be asked to execute Team Lead duties.
  • Travel in support of audits and agency visits may be required. 

 Knowledge, Skills, and Abilities Required

  • Experience in analyzing and interpreting qualitative and quantitative data/results.
  • Excellent organizational and communication skills.
  • Exceptional analytical, critical thinking and problem solving skills.
  • Strong knowledge of customer service techniques and processes.
  • Excellent written and oral communication skills.
  • Ability to multitask and work under pressure.
  • Project Leadership skills.
  • Sound knowledge of Microsoft Office with excellent EXCEL skills 

Education & Experience

  • The ideal candidate will possess 3 – 5 years of relevant experience
  • Personal Lines Auto experience preferred.
  • P&C License preferred and required within first year of employment


About Plymouth Rock  

Plymouth Rock is a leading auto insurance provider serving more than 650,000 customers across Connecticut, Massachusetts, New Jersey, New Hampshire and Pennsylvania. Tapping into its 30+ years of industry experience, Plymouth Rock has pioneered a new way to do car insurance for consumers. Combining the local knowledge and expertise of independent agents, with the power and ease of doing business online, Plymouth Rock has changed the insurance lifecycle by giving consumers choice – to do business the way they want.
Plymouth Rock is headquartered across from South Station in Downtown Boston, with offices across New England and New Jersey. With more than $1 billion in premiums underwritten and serviced, the Plymouth Rock Group employs over 1,500 people and writes insurance through 800+ independent agents. Plymouth Rock Assurance Corporation holds an A.M. Best rating of “A-/Excellent.”


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