Plymouth Rock Assurance Video

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Plymouth Rock Assurance – Why Work For Us?

In 1982, Jim Stone, former insurance commissioner for the Commonwealth of Massachusetts, had a vision for the future.

He would form a new kind of auto insurance company - one that would:

* Define a new, higher standard of customer service for the industry;

* Establish deeper, more productive relationships with its independent agents;

* Provide an unusually rewarding workplace for creative, empowered employees; and

* Develop a new generation of technological and analytical tools for every aspect of the business.


Today, Plymouth Rock Assurance is a thriving business that takes pride in delivering more than just insurance — we deliver the added assurance of great value, ease, service and innovation.

Plymouth Rock Assurance is a member of The Plymouth Rock Group of Companies which together write and manage over $1 billion in annual automobile and homeowners’ insurance premiums. Plymouth Rock Assurance is rated "A-/Excellent" for financial strength by the A.M. Best Company.

The Plymouth Rock Group of Companies includes:

  • Plymouth Rock Assurance Corporation
  • Bunker Hill Insurance Company
  • Pilgrim Insurance Company
  • Mt. Washington Assurance Corporation
  • Plymouth Rock Management Company of New Jersey 
  • InsuraMatch

Plymouth Rock Assurance Corporation is licensed in Massachusetts and Connecticut. Our principal office is located at 695 Atlantic Avenue, Boston, MA 02111.

Plymouth Rock Assurance Corporation now sells and services personal and commercial auto insurance in Massachusetts and Connecticut through a network of more than 500 local independent agents. We began with a promise to ourselves, our agents and our policyholders:

  • To hire smart, capable people dedicated to providing exceptional service.

  • To offer cutting edge technology for fast, accurate processing.

  • To deliver premium claim services that would make our customers’ lives easier when they need us most.

Our Company admires friendliness, good citizenship, integrity, loyalty, hard work, and the pursuit of excellence.

Our Company admires friendliness, good citizenship, integrity, loyalty, hard work, and the pursuit of excellence. We believe that a shared philosophy reinforces our cooperative accomplishments. We are forthright about the kind of company we strive to be. We are constantly looking as we grow for more employees who share our values. We want our people to be happier with us than they could be anywhere else.  Here are some suggestions we want to call to the attention of all new employees as they learn our culture.  

Put Service First

Our approach to business requires that we attract and keep the best agents and the best customers. We deserve to get the best business only if we offer the most in return. This takes a zealous commitment to service. We should aim to be better at service than anyone else in our business, and to be known for that above all else.

Do It Now

Unnecessary delay is anathema to excellence. Backlogs are much harder to cure than to prevent. There is nothing wrong with getting help to prevent a backlog; there is no heroism in facing a backlog alone. A sense of urgency underscores our commitment to quality.

Be Friendly

We spend nearly half our waking hours at work. Our jobs should not only offer satisfaction from the technical work, but also a sense of companionship with our co-workers. Someone who does every technical assignment perfectly but doesn’t contribute to the happiness of others has done only half the job right. Take responsibility for making every employee feel good about being with us and working hard, just as we need to make every agent and every customer feel good about choosing us to do business with.

Maintain Our Workplace

Messy spaces create stress. Everyone feels better when the environment is orderly and calm.  So, be attentive to the appearance of the office. Each of us should feel responsible for all visible spaces.  Our offices should look at every moment as though we were about to show them off to an important visitor.

Call Attention to Problems

We all feel overwhelmed by our assignments from time to time.  Call for help when these situations arise. When a co-worker is struggling, always offer help and then make sure the problem gets solved, even if this requires finding someone higher up to fix whatever is wrong. We should all have a sense of responsibility for any problem we see and stay with it until it is resolved. Hiding a problem is the worst thing to do; ignoring a problem, even if it appears to be someone else’s, is almost as harmful.

Seek Constant Improvement

Everything we do at work can be improved upon. Everyone is invited to suggest ways to streamline existing procedures and get rid of unnecessary, boring tasks. We should always be receptive to new technologies and improved approaches. We should be quick to comment, though, when a new idea or experiment isn’t working as hoped. Failed experiments are part of seeking progress too.

Treat People with Respect

Everyone deserves to be treated with respect, especially when working together toward a common success. It is disrespectful to refuse to listen to someone else’s views or to fall prey to hateful biases and prejudices. Our goal is always to treat people with courtesy, civility, and kindness. Mutual respect creates increased job satisfaction, longer tenures, and greater effectiveness.

Communicate About Worries

A job is a relationship between an employee and a company, and as is the case with all human relationships, no one should expect it to be perfect. When an employee feels that something has gone wrong in a job, the Company needs to know that. This usually means bringing the matter to a higher level. Sometimes the Company has made an error and can fix it; sometimes the employee has something to learn. Nothing happens, though, until the problem or disappointment has been brought into the open. Work stresses should not be kept stewing inside, and it does no good to share complaints with people unable to resolve them. Active and constructive communication is the beginning of most solutions.

Be Smart but Not Smug

We should pride ourselves on innovative approaches, and admire people who use their brains to the fullest. We tend to hire and promote people who seek education. On the other hand, there is an infinite amount we do not know. It is imperative that we never get smug about our level of knowledge or our degree of sophistication. Smugness is the worst enemy of creative intellect.

Maintain a Professional Demeanor

Ours is a business office and conduct within it should always reflect professionalism. It’s not businesslike to use publicly visible work stations for activities other than work, to play music that disturbs others or cuts us off from communications, or to dress in too casual a manner. We want to dress, walk, and talk like the respected professionals we strive to be.

Know Your Colleagues

Everyone likes working with friends, and we all want a sense that the Company pays personal attention to our needs and our successes. Our staff is encouraged to recruit friends for jobs in the Company. All employees are asked to get to know the people they work with and be sensitive to them as individuals. Supervisors should have small enough spans of authority to pay attention to every aspect of each person’s performance and be empathetic to their feelings. We each have to do our part, though, to make this closeness work. It requires an extra hello, an occasional social visit, and a host of the other small attentions that add up to warmth among people.

Be Proud of Where You Work

Our Company is a community. People feel best when they are proud of their community and know that it is accomplishing something worthwhile. If there are questions about how one’s work fits into the whole picture or about the behavior of the Company in any area of its work, it is always good to ask. When the Company is mentioned outside our offices, we should all be able to speak about it with pride and a broad base of knowledge. We want to be honest and good citizens, both individually and as a group.

More than insurance jobs…insurance careers

Plymouth Rock Assurance and its affiliates have experienced steady growth over the past 26 years and, despite today’s economy, are still hiring for new positions throughout the Plymouth Rock Group of Companies.

Looking for rewarding insurance jobs? The Plymouth Rock Group prides itself on hiring smart, creative and collegial people and providing them with a challenging, entrepreneurial work environment.

Employees are expected to be collaborative and inclusive in their approach to solving problems. A published 12-point Culture Statement provides the basis for employees’ commitment to excellence, to superior customer service, and to one another. Our commitment to fostering a quality work environment is reflected in our exceptionally low employee turnover rate.

Plymouth Rock Assurance and its affiliates offer their employees insurance jobs with competitive salaries and benefits, with some unique extras.

Plymouth Rock Assurance Photos

Plymouth Rock Assurance Reviews

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Plymouth Rock Assurance President Chris Olie
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    Current Employee - Anonymous Employee
    Current Employee - Anonymous Employee
    Positive Outlook
    Approves of CEO


    Great benefits, good work environment. Everyone seems to be willing to help answer any questions you have, and there is a team spirit to get the job done.


    Salary is on the average to low side, hard/slow advancement opportunites. Although close to the MBTA, you are always expected to make it in, regardless of the weather.

    Advice to Management

    Reward those employees who continuously strive to out perform.

Plymouth Rock Assurance Interviews

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Interview Experience


Getting an Interview

Getting an Interview


Interview Difficulty


Interview Difficulty




    Claims Representative Interview

    Anonymous Interview Candidate in Red Bank, NJ
    No Offer
    Negative Experience
    Average Interview


    I applied through an employee referral. I interviewed at Plymouth Rock Assurance (Red Bank, NJ) in September 2015.


    About 1 1/2 hours. Interviewed by two individuals in upper level management. Was told that they would be doing second round interviews and they would be calling to let me know if I would be called to these interviews, or if other applicants were a better fit. Never received any information from anyone in the company. Recruiter in HR never returned my call either after waiting 3 weeks for any type of an answer. All parties seemed nice, but unfortunately lack professionalism.

    Interview Questions

Plymouth Rock Assurance Awards & Accolades

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Top Places to Work , The Boston Globe, 2014

Additional Info

Headquarters Boston, MA
Size 501 to 1000 Employees
Founded 1982
Type Company - Private
Industry Insurance
Revenue $10 to $25 million (USD) per year

Plymouth Rock Assurance is a Massachusetts-based auto insurance provider serving drivers in Massachusetts and Connecticut. We’ve been offering great rates on car insurance for more than 30 years. Coverage options you can count on and more. Get a free auto insurance quote online, with the added benefit of friendly, knowledgeable service from local independent agents ... More

Mission: We seek to be the premier New England regional writer of auto insurance, achieved through a combination of extraordinary service and competitive rates.

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