When it comes to our people, Plymouth Rock listens to every voice. Seriously, if you work here, your point of view is not only encouraged, it’s expected. Doesn’t matter what your job title is either.
Some companies call it diversity of thought—we just call it common sense. Listening to our people is the only way we know how to innovate and drive our work forward.
Can you check these boxes?
- Fun
- Consumer focused
- Smart
- Interested in learning
- Ambitious
- Eager to collaborate
- Courageous
- Inventive
- Driven to WIN!
- Fun
- Consumer focused
- Smart
- Interested in learning
- Ambitious
- Eager to collaborate
- Courageous
- Inventive
- Driven to WIN!
We want you to be happier here than anywhere else. That’s why we’ve created a welcoming and rewarding corporate culture!
You won't find:
- Rigid workplace rules
- Layers of bureaucracy
- Killer work hours
- Antiquated, dank offices
- Stuffy executives
VS
You will find:
- A fun, informal work setting
- Plenty of chances to grow
- Healthy work-life balance
- Modern workspaces
- Execs with open-door policies
Values
Recognition
Fun
We offer a comprehensive benefits package to support all aspects of employee wellness. Our benefits are designed to promote good health, work-life balance and financial stability.
Health & well-being
Financial wellness
Time off & family support
Perks
Health & well-being
Health & well-being
We offer multiple plans for medical, dental and vision coverage. Employee contributions, deductibles and co-pays are lower than most companies.
- Eligibility for benefits starts on the first day of employment
- Three generous health insurance options subsidizing 10% more than industry competitors with no lifetime maximums, and employer contribution towards HSA
- Various in-person and virtual mental health resources
- Health & fitness reimbursements
- Wellness program: earn cash for being active, sleeping well and eating right
- Free condition support programs including Diabetes care, back and joint pain, cancer, and fertility support
Financial wellness
Financial wellness
We offer several benefits to foster financial wellness including our generous 401(k) employer contribution.
- 401(k) plan allows employees to save on a pre-tax, Roth and traditional after-tax basis
- 401(k) employer contribution worth 7.5% of your annual base salary regardless of how much you contribute to your 401k
- Pre-tax spending accounts
- Commuter benefits
- Company paid life insurance and buy-up options including Long Term Care
- Free financial education and access to Certified Financial Planners
- Tuition reimbursement
- Employee referral bonus
Time off & family support
Time off & family support
At Plymouth Rock, we care about you and your family. That is why we have benefits that support a healthy work-life balance, including generous time off and family care services.
- Paid time off from 20 to 30 days based on years of service
- 9 paid office holidays
- Employee Assistance Program (EAP) for mental health needs for employees and families
- Company paid short-term and long-term disability
- Support and reimbursement programs for fertility, adoption and surrogacy
- Parental leave paid at 100% for the first four weeks; plus eight weeks at applicable state pay limits
- Paid family leave to care for family members at applicable state pay limits
- Caregiving concierge service for employees and family members at no cost
- Five days of paid bereavement leave for loss of a family member including pregnancy loss
- Voluntary benefits: Pet Insurance, Legal Plan, Identity Protection
Perks
Perks
Our offices foster an empowering work environment with great perks and events throughout the year.
- Employee recognition program
- On-site training and access to over 9,000 LinkedIn learning courses
- Employee discounts including auto insurance
- Volunteer day opportunities
- Free on-site gym and health center in Woodbridge, NJ location
- Free on-site gym and nurse in Boston, MA location
- Various in-office events
- Company summer outing and holiday party
Plymouth Rock has been included in Forbes’ America’s Best Insurance Companies 2025 ranking for both its Auto and Homeowners products. The ranking was determined based on an independent survey of over 18,000 U.S. citizens across the nation.
Woodbridge, NJ
2021 Top Work Places,
NJ.com, Ranked #1,
Large Employer in New Jersey
Based on an anonymous employee survey.
Boston MA
2020 Top Places to Work,
Boston Globe, Ranked #17,
Large Company in Massachusetts
Based on an anonymous employee survey.
Plymouth Rock serves customers in six states—so naturally we have offices in six states! It’s like we always say, “There’s no expertise like local expertise!”
BOSTON, MA
WOODBRIDGE, NJ
UNIONDALE, NY
OTHER CITIES
One of our most treasured values is Good Citizenship. To us, that means helping people in the communities where we live and work.
Matching gift program
Our best-in-class Matching Gift Program epitomizes Plymouth Rock culture.
- We offer employees a generous 2:1 matching opportunity. For example: If an employee donates $500 to a qualified charity, we’ll donate an extra $1,000
- Less than 1 in 20 companies match employee donations at a rate greater than 1:1
Plymouth Rock Assurance foundation
Our Foundation has been awarding grants and scholarships for over two decades.
- Since 1996, the Foundation has given away $8 million to non-profit organizations
- In March 2021, we donated $500,000 to organizations helping students affected by COVID-19
- Focus areas: Education, youth programs, health care, environmental causes, workplace development
Community service
- Holiday toy drives
- Earth Day cleanups
- Youth Mentoring
