The Plymouth Rock group of companies write and manage more than $2 billion in property and casualty insurance across Connecticut, Massachusetts, New Hampshire, New Jersey, New York and Pennsylvania, where we have built an unparalleled reputation for service. We continuously invest in our employees and thrive in our empowering environment, and our customers are among the most loyal in the industry. As we grow, we continue to seek out passionate, driven professionals who share our values – people looking to bring their insight and abilities to an organization that appreciates intelligence, integrity, and the pursuit of excellence.

The Expertise We Seek

We seek to add an experienced attorney to our in-house legal team who will work directly with our General Counsel and Deputy General Counsel and provide counsel and advice to our various business units on a variety of matters, including insurance and regulatory requirements, vendor management, corporate governance, employee relations, marketing, transactional and other operational issues.  

The successful candidate will demonstrate an ability to achieve a full understanding of our business and operational strategies to ensure sound legal counsel and advice in all matters affecting our business affairs and legal and regulatory compliance.  We seek an individual who possesses exceptional judgment and an ability to analyze quickly complex legal and business issues in a wide variety of substantive areas.  The mandate is to deliver solutions-oriented counsel while identifying and mitigating risks. 

Here is what you will do:

• Evaluate legal implications of business objectives and provide counsel to determine best approaches to achieve desired strategic goals
• Participate in cross-functional working teams in the development of products and services
• Review and negotiate business/vendor contracts, including licensing agreements
• Monitor and research pending legislation and regulation related to the companies’ business needs
• Review and advise on marketing materials
• Assist in analysis, negotiation, and implementation of acquisitions and other corporate transactions
• Manage and update various company policies and provide ongoing employee training
• Effectively communicate and collaborate with internal clients, as well as the General Counsel, Deputy General Counsel and other legal department attorneys

Here is what you will bring to the table:

• The ideal candidate will possess 7 or more years of litigation, insurance, regulatory or corporate experience in a dynamic in-house legal setting, a major law firm or regulatory agency
• Proven capability to approach and successfully navigate complex situations; persuading others to take actions in a diplomatic and respectful manner
• Excellent analytical, advocacy, and interpersonal skills, as well as the ability to advise and influence senior executives and professionals from diverse businesses.
• Superior writing and oral communication skills and ability to research and interpret complex regulations
• Willingness to work hard and balance a variety of assignments associated with a small legal department
• Demonstrates ownership, independence, and self-motivation to bring assignments to a successful conclusion
• Highest level of integrity and ethics, both professional and personal
• Juris Doctor degree
• Admitted to the practice of law in Massachusetts or other jurisdiction in the company’s footprint

Why work for us:

• 4 weeks accrued paid time off + 9 paid national holidays per year
• Remote work equipment
• Tuition Reimbursement 
• Low cost and excellent coverage health insurance options (medical, dental, vision)
• Gym membership reimbursement
• 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
• $3,000 one-time bonus payment on health insurance waiver

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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