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.

We believe that a shared philosophy reinforces our cooperative accomplishments. We are very forthright about the kind of company we strive to be. Employees who do not share these values will probably not be happy being with us. We are constantly looking as we grow for more employees who do share these values. We want them to be happier with us than they could be anywhere else. The Plymouth Rock Group of Companies has a unique corporate culture and has developed a series of principles that makes this a special place to work.

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 an anathema to excellence. Doing work the moment it is possible to do so prevents backlogs, and 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 letting a backlog build and facing it alone. A sense of urgency underscores our commitment to quality and our intolerance of sloppiness, laziness and indifference.

Be Friendly

We spend nearly half our waking hours at work. Our jobs should have two rewarding components: a sense of satisfaction from the technical work and a sense of companionship with our co-workers. Someone who does every technical assignment perfectly but doesn't contribute to the work and the happiness of others has done only half the job right. We should all 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 to do business with us.

Maintain Our Workplace

Messy spaces and half-finished work papers create stress and a sense of chaos. Everyone feels better when the environment is orderly and calm. Unfortunately, it requires a great deal of effort to keep our work spaces neat. So, be fanatical about the appearance of the office. We should leave only current projects in view and keep window sills, cabinet tops and radiators clear. Everyone should feel responsible for common spaces. We should make our offices look at every moment as though we were about to show them off to the most important visitor we can think of.

Call Attention to Problems

We all feel overwhelmed by our assignments from time to time. Everyone should feel free to call for help when these situations arise. If a co-worker is struggling, always offer help and then make sure the problem gets solved. This generally requires finding someone who can fix whatever is wrong. If the first person alerted does not fix the problem, keep trying until someone does, even if that means going very high up in the Company. 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 problem, is almost as harmful.

Seek Constant Improvement

Everything we do at work can be improved upon. We should never hesitate to make recommendations for change that will enhance productivity. Everyone is invited to find ways to streamline existing procedures and get rid of unnecessary and boring tasks. We should always be receptive to state-of-the-art technologies and scientific approaches. We should all be quick to comment, though, if 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 be rude or insulting. Bias and prejudice are also forms of disrespect and have no place in our offices. Our goal is to treat people the way we would want to be treated — with courtesy, civility and respect. We should be known by our customers, agents and other business acquaintances for the respect we show them and each other. Mutual respect creates a positive work environment, with fewer distractions and stresses, increased job satisfaction and 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 hire people with more education than other companies do, and we give preference in promotions to those who have come to us with, or have added, educational accomplishments. 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 business-like to eat lunch or read recreationally at publicly visible work stations, to play music that disturbs others or cuts us off from communications, to chat for long periods in hallways or to dress too casually. 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 successes. Our staff is encouraged to recruit relatives and good 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. The Company is organized into small units so that people can work closely together in stable teams. Supervisors who have only five or six people in their group can 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 and learn. 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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    • Work/Life Balance
    • Culture & Values
    • Career Opportunities
    • Comp & Benefits
    • Senior Management
    Current Employee - Anonymous Employee
    Current Employee - Anonymous Employee

    I have been working at Plymouth Rock Assurance

    Positive Outlook
    Approves of CEO
    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

Interview Experience

Interview Experience


Getting an Interview

Getting an Interview


Interview Difficulty


Interview Difficulty




    QA Interview

    Anonymous Interview Candidate in Boston, MA
    Accepted Offer
    Positive Experience
    Average Interview


    I applied through an employee referral. The process took 3 daysinterviewed at Plymouth Rock Assurance (Boston, MA).


    I was working as a consultant at the company for over a year and a half when I was offered the choice to take up a permanent position and they file my paperwork for getting permanent residence or Green Card to stay in the US. I also change my license from michigan to massachusetts and got a new Sim Card from AT&T.

    Interview Questions


    It was an internal hire and I got a reference from another colleague at work. The other reference was from the staffing company I worked with the my QA Lead.

Plymouth Rock Assurance Awards & Accolades

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Top Places to Work, The Boston Globe, 2014

Additional Info

Headquarters Boston, MA
Size 500 to 999 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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