--- title: Plymouth Rock Assurance Jobs & Careers — Insurance description: Explore Plymouth Rock Assurance careers in auto and home insurance. Browse claims, actuarial, technology, and underwriting roles across the northeastern United States. type: company url: https://www.foundrole.com/companies/plymouth-rock-assurance date: 2026-06-01T08:08:10Z og_description: Plymouth Rock Assurance is a regional property and casualty insurer managing over $2 billion in auto and home premiums across six northeastern states. Browse careers in claims, technology, actuarial, and insurance operations. og_image: https://www.foundrole.com/img/pages/ns617c/plymouth-rock-assurance.png?v=3 breadcrumbs: - label: Home url: https://www.foundrole.com/ - label: Sectors url: https://www.foundrole.com/sectors - label: Insurance url: https://www.foundrole.com/sectors/insurance - label: Insurance Carriers url: https://www.foundrole.com/sectors/insurance/insurance-carriers-2 --- # Plymouth Rock Assurance Jobs & Careers — Insurance | | | |---|---| | **Industry** | Insurance | | **Rating** | 3.5 | | **Size** | 1,001-5,000 employees | | **Headquarters** | Boston, MA | | **Founded** | 1982 | | **Website** | https://www.plymouthrock.com/ | ## Market Insights — June 2026 *Based on 68 postings analyzed in June 2026 • Updated June 1, 2026* How does compensation at Plymouth Rock Assurance stack up against the broader insurance market? Pay runs 31% above the sitewide median at $109K, a substantial edge that reflects the company's positioning in the segment. Hiring activity surged dramatically this month, jumping from a single opening to 16 active postings—a rare spike that signals meaningful headcount expansion. All roles remain office-based; the absence of remote flexibility narrows the candidate pool to those able to work on-site, a constraint that may intensify competition for the newly available seats. - Hiring at Plymouth Rock Assurance accelerated 1500% this month (16 active vs 1 last month). - Pay at Plymouth Rock Assurance runs 31% above the sitewide median ($109K vs $83K). - Remote share at Plymouth Rock Assurance held steady around 0% (vs 0% last month). *Numbers above are computed from active job postings indexed during the snapshot window. Salary figures use posted ranges where available; sitewide medians are recomputed monthly from the full index. Confidence reflects sample size and signal stability vs the prior month.* ## About Plymouth Rock Assurance is a regional property and casualty insurance company headquartered in Boston, Massachusetts. Founded in 1982 by former Massachusetts Insurance Commissioner Jim Stone, the company writes and manages auto and home insurance across six northeastern states and holds an A.M. Best 'Excellent' financial rating. ## History Jim Stone founded Plymouth Rock in 1982 with a specific goal: raise the bar for customer service in the auto insurance industry. The company grew steadily through the 1990s and 2000s, expanding from Massachusetts into New Jersey, Connecticut, New Hampshire, New York, and Pennsylvania. It has earned Top Places to Work recognition in Massachusetts and New Jersey as its workforce has grown. ## Markets & Services Plymouth Rock focuses on personal lines property and casualty insurance. Core areas include: - **Auto Insurance** — private passenger auto coverage across six northeastern states - **Home Insurance** — homeowners and renters coverage tied to regional markets - **Claims Operations** — in-house claims handling with structured training pathways - **Actuarial & Underwriting** — pricing, risk analysis, and policy management - **Community & Corporate Citizenship** — philanthropy and volunteer engagement programs tied to company values## Mission Plymouth Rock is all about good service and good citizenship — delivering high-quality service to customers, agents, employees, and communities, while investing in employees, serving communities through philanthropy and volunteer engagement, and practicing environmental stewardship.## Open Positions 10+ open positions at Plymouth Rock Assurance. - [Senior Claims Representative, Bodily Injury](https://www.foundrole.com/companies/plymouth-rock-assurance?job=senior-claims-representative-bodily-injury-in-07054-parsippany-nj-i2t3543&tab=jobs) — 2 locations - [Sr. Field Auto Damage Appraiser](https://www.foundrole.com/companies/plymouth-rock-assurance?job=sr-field-auto-damage-appraiser-in-07054-parsippany-nj-s5rud4f&tab=jobs) — Parsippany, NJ - [Senior Data Analyst](https://www.foundrole.com/companies/plymouth-rock-assurance?job=senior-data-analyst-in-07095-woodbridge-nj-pz28l2i&tab=jobs) — Woodbridge, NJ - [Accounting, Treasury](https://www.foundrole.com/companies/plymouth-rock-assurance?job=accounting-treasury-in-07095-woodbridge-nj-wkswswa&tab=jobs) — Woodbridge, NJ - [Claims Associate, Rental](https://www.foundrole.com/companies/plymouth-rock-assurance?job=claims-associate-rental-in-07054-parsippany-nj-w7zqft9&tab=jobs) — Parsippany, NJ [View all Plymouth Rock Assurance jobs →](https://www.foundrole.com/companies/plymouth-rock-assurance?tab=jobs) ## Top Roles Hired For - Lawyer — $137K median ($119K–$138K range) (20 jobs) - Claims Specialist / Adjuster / Examiner — $73K median ($65K–$87K range) (19 jobs) - Financial Manager — $181K median ($181K–$235K range) (9 jobs) - Insurance Claims / Policy Clerk — $54K median ($49K–$79K range) (8 jobs) - Product Analyst — $55K median ($55K–$55K range) (4 jobs) ## Hiring Activity Monthly open-role counts for Plymouth Rock Assurance (median of third-party job-count snapshots): - April 2026: 15 open roles - May 2026: 21 open roles - June 2026: 19 open roles ## Tech Stack Most-used tools and platforms across Plymouth Rock Assurance's active jobs, grouped by subcategory: **IT Automation:** Automation (7%), Kubernetes (5%), Terraform (5%), Ansible (2%) **Cloud Solutions:** Microsoft Azure (2%), Amazon Virtual Private Cloud (VPC) (2%), Google Cloud Platform (GCP) (2%), Amazon CloudWatch (2%), Amazon Elastic Kubernetes Service (2%) **Cybersecurity:** Security Controls (2%), Threat Modeling (2%), Access Controls (2%), Data Security (2%), Cyber Security (2%) **Software Development:** DevOps (5%), Application Development (2%), Software Development (2%) **Computer Science:** Computer Science (7%), Information Systems (2%) **IT Management:** Prometheus (5%), Infrastructure as Code (IaC) (5%) ## Domain Expertise Specialized knowledge areas across Plymouth Rock Assurance's active jobs: **Forestry:** logging (5%) **Health Care Administration:** Medical Management (2%) **Software Development:** Software Features (2%) **Cybersecurity:** cloud security and compliance (2%) **Regulation and Legal Compliance:** architecture regulations (2%) ## Certifications Professional certifications across Plymouth Rock Assurance's active jobs: **Emergency and Intensive Care:** Advanced Cardiovascular Life Support (ACLS) (2%) **Architectural Design:** Professional Architect (2%) ## Common Tools Tools and capabilities Plymouth Rock Assurance emphasizes more than the typical employer (IDF-weighted, so universally-mentioned skills don't dominate): **Physical Security:** Security Policies **Computer Science:** Information Technology **Quality Assurance and Control:** Quality Assurance **Teaching:** Mentorship **Office and Productivity Software:** Microsoft Office ## Soft Skills Soft skills emphasized in Plymouth Rock Assurance's active job requirements: **Soft Skills:** Organizational Skills (2%), Written Communication (2%), Critical Thinking (2%), Time Management (2%), Leadership (2%) ## Benefits Benefits offered across Plymouth Rock Assurance's active jobs (each appearing in at least 30% of postings): **Education and Career Development:** Financial Aid/Assistance (75%), Professional Development (75%) **Health and Wellness Benefits:** Health and Wellness Programs (75%) **Insurance:** Health Insurance (75%) **Paid Leave:** Parental Leave (75%), Paid Time Off (PTO) (75%), Floating Holidays (61%) **Retirement and Savings:** 401(k) Plans (75%) ## Industry Focus **Industries:** Insurance **Sectors:** Insurance ## Frequently Asked Questions ### What does Plymouth Rock Assurance do? Plymouth Rock Assurance is a regional property and casualty insurance company writing and managing auto and home insurance across Massachusetts, New Jersey, Connecticut, New Hampshire, New York, and Pennsylvania. Founded in 1982, the company manages over $2 billion in premiums and holds an A.M. Best 'Excellent' financial rating. ### Where is Plymouth Rock Assurance headquartered? Plymouth Rock Assurance is headquartered in Boston, Massachusetts. The company operates across six northeastern states, with significant hiring activity in New Jersey and Pennsylvania in addition to its Massachusetts base. ### What types of jobs are available at Plymouth Rock Assurance? Plymouth Rock hires across claims handling, claims supervision, actuarial analysis, underwriting, digital design, technology, compliance, customer service, and corporate functions. Structured training programs support entry-level claims roles, making it accessible for early-career candidates. ### Is Plymouth Rock Assurance a good place to work? Plymouth Rock Assurance holds a 3.5 Glassdoor rating. The company has earned Top Places to Work recognition in both Massachusetts and New Jersey. Employees note competitive benefits and a community-focused culture grounded in the company's philanthropic and volunteer engagement commitments. ### Who founded Plymouth Rock Assurance? Plymouth Rock Assurance was founded in 1982 by Jim Stone, a former Massachusetts Insurance Commissioner. Stone founded the company with the goal of setting a higher standard for customer service in the auto insurance industry. The company remains privately held. ## Related - [Browse all companies](https://www.foundrole.com/companies) - [GEICO Jobs & Careers — Auto & Property Insurance](https://www.foundrole.com/companies/geico) - [State Farm Jobs & Careers — Insurance & Financial](https://www.foundrole.com/companies/state-farm) - [Farm Bureau Financial Services Jobs & Careers](https://www.foundrole.com/companies/farm-bureau-financial-services) - [Gallagher Bassett Jobs & Careers — Claims Management](https://www.foundrole.com/companies/gallagher-bassett) - [Brown & Brown Jobs & Careers — Insurance Brokerage](https://www.foundrole.com/companies/brown-brown-insurance)