Job Description

At Plymouth Rock Assurance, our field team serves as the face of the company during some of our customers’ most difficult moments. As an Associate Field Inspector, you will play a critical role in supporting the claims process by conducting on-site inspections, documenting damages, and providing accurate field information to the handling adjuster.

This position is designed as a developmental role with a clear growth path into a fully independent Property Field Adjuster position. Through hands-on training, mentorship, and field experience, you will build the skills necessary to investigate losses, write estimates, and ultimately manage and settle property claims independently.

No prior insurance experience is required. Candidates with backgrounds in construction, restoration, mitigation, roofing, remodeling, customer service, or other field-based industries are encouraged to apply.

Responsibilities

• Serve as a professional and compassionate representative of Plymouth Rock during on-site customer interactions
• Travel daily to insured properties to inspect and document damages
• Capture detailed photographs, measurements, notes, and other field documentation to support the claim investigation
• Relay inspection findings clearly and accurately to the handling adjuster
• Assist with identifying scope of damage and potential repair concerns
• Support the claims process by coordinating with policyholders, contractors, mitigation vendors, and internal team members
• Maintain proactive communication and help set clear expectations for customers throughout the inspection process
• Learn property estimating, coverage analysis, and claim handling fundamentals through training and mentorship
• Progress toward independently writing estimates and managing property claims

Travel expectations vary, but candidates should expect to routinely travel one to two hours from home on a daily basis.

Qualifications

• Strong customer service and communication skills
• Comfortable working independently in the field while staying connected with a collaborative team
• Ability to learn quickly and adapt in a fast-paced environment
• Strong attention to detail and organizational skills
• Self-motivated with a desire to grow into a Property Field Adjuster role
• Experience in construction, mitigation, remediation, roofing, restoration, or related industries is preferred but not required
• Bachelor’s Degree preferred but not required
• Proficiency with mobile technology and Microsoft Office applications
• Valid Driver’s License and safe driving record
• Ability to carry up to 25 pounds and perform roof inspections on homes under two stories
• Ability to obtain applicable adjuster licensing and complete continuing education requirements as needed

Salary Range: $50,000 - $67,000 a yearActual compensation will vary based on multiple factors, including employee knowledge and experience, role scope, business needs, geographical location, and internal equity.

Perks and Benefits

• 4 weeks accrued paid time off + 9 paid national holidays per year
• 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
• Remote work equipment

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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