The Plymouth Rock Company Incorporated jobs

About the Company The Plymouth Rock Company and its affiliated group of companies write and manage over $2.4 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 2,000 people and is headquartered in Boston, Massachusetts. Plymouth Rock Assurance Corporation holds an A.M. Best rating of “A-/Excellent”. About the Role The Customer Experience (CX) Program Director is responsible for leading the vision, strategy, and execution of customer insights initiatives across the organization. This role synthesizes data from multiple sources to drive actionable outcomes, foster a customer-centric culture, and enhance customer value across the entire lifecycle. The role requires strong leadership, strategic thinking, and collaboration across cross-functional teams without direct reporting authority. Responsibilities Lead and manage cross-functional CX initiatives aligned with business goals. Translate customer insights from voice analytics, automated QA, social media, and third-party sources (e.g., J.D. Power) into strategic actions. Conduct root cause and driver analysis, segmentation, and journey mapping to uncover friction points and improvement opportunities. Design and execute surveys, usability testing, and qualitative research initiatives. Establish a company-wide customer success strategy through integrated processes, content, and data. Develop and maintain a full customer lifecycle model to ensure measurable value realization at every stage. Maintain repositories of insights, action libraries, trends, and customer data. Serve as a subject matter expert in voice/text transcript analytics and optimize their use. Create and evolve programs that drive customer lifetime value and deliver business impact. Champion a continuous customer feedback loop across the organization; advocate for the voice of the customer and embed customer-centric thinking in key decisions. Design surveys and report on customer experience outcomes to leadership. Qualifications 10+ years of experience in CX leadership roles. Proven expertise in customer research, data analysis, and experience design. Strong stakeholder influence, executive communication, and storytelling skills. Demonstrated ability to lead cross-functional projects and drive results without direct authority. Experience in the Property & Casualty Insurance industry is preferred. Bachelor's degree required; MBA or relevant advanced degree preferred. Required Skills CX strategy, research methods, stakeholder cadence, engagement, and executive communication. Managing data, drawing conclusions, and sharing recommendations for buy in. Survey and CX platforms, sampling logic, A/B testing, insights into new tools and capabilities. Optimizes customer voice platforms. Develop a deep understanding of Plymouth Rock customers. Perks and benefits 4 weeks accrued paid time off + 9 paid national holidays per year Free onsite gym at our Boston Location Tuition Reimbursement Low cost and excellent coverage health insurance options that start on Day 1 (medical, dental, vision) 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 Resources to promote Professional Development (LinkedIn Learning and licensure assistance) Convenient location directly across from South Station and Pre-Tax Commuter Benefits ```

Our Boston Actuarial team is seeking a self-motivated and creative individual with a strong desire to work with Product Management, Claims, and Finance to bring statistical rigor and analysis into everyday processes. The ideal candidate will have a strong business sense and a proven track record of generating new ideas across an organization and implementing those into current operations. The individual in this position supports the Actuarial Manager and team by identifying business issues, performing analysis to understand the drivers of the issues, and making recommendations to improve overall business results. This includes performing analysis within a designated business segment to assess reserves and profitability of the segment as well as financial planning. Responsibilities Conduct indications analysis, working with Product Managers to assess and forecast impacts of product, market, and economic changes on profitability and rate need Collaborate with Finance and Product to forecast premiums and losses; assessing the expected variability in those forecasts; Conduct reserving analysis, using both traditional and non-traditional methods; develop new methods and incorporate them as warranted. Model weather events, economic changes and/or business mix changes and their impact on reserves and rate need; Estimate the impact of claim practices and business mix changes on reserves and reserve variability; develop and analyze key metrics and exhibits to facilitate this estimation. Effectively communicate results of analysis to peers and senior management across the organization, both in writing and in presentations. Maintain an external network within the insurance industry to track emerging trends and approaches to business issues. Provide supervision and training to actuarial interns and junior staff. Serve as a mentor to other department members on aspects of project work, insurance and general business knowledge. Qualifications Associate of the Casualty Actuarial Society (ACAS); 4-6+ years of work experience in analyzing P&C insurance with practical application of statistical techniques and models; Excellent communication and interpersonal skills, allowing effective interaction with colleagues and executives; Excellent statistical, programming, and data management skills; Strong project management skills to carry ideas through to completion Perks and Benefits 4 weeks accrued paid time off + 9 paid national holidays per year Tuition Reimbursement Low cost and excellent coverage health insurance options that start on Day 1 (medical, dental, vision) 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 Resources to promote Professional Development (LinkedIn Learning and licensure assistance) Convenient location directly across from South Station and Pre-Tax Commuter Benefits 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”

You're not just in it to win it. You want to crush it every time. Because that's what our sales professionals do. Not just anyone has what it takes to build strong and profitable relationships. If you're a unique performer, Sentry offers a career opportunity that soars beyond commercial insurance sales. Our highly trained Account Executives present specialized commercial insurance, 401K, and life insurance products that are perfectly designed for the industries we serve. We provide everything you need to carve out a sales career filled with success and purpose, including: High earning potential with base salary, commissions, monthly/annual incentives, plus recognition trips Outstanding benefits and a 401(k)-program matching dollar for dollar up to 8% Opportunities for professional development and growth Outstanding training and support An industry-leading line of products and services Total currently estimated projected compensation range for this position is $134,793-$170,793, which is a combination of base pay, currently projected renewal commissions, and currently estimated new business commission opportunities. Commission opportunities - both renewal and new business -- are based on achievement of sales objectives and compliance with the terms of the applicable incentive plan. The California and Nevada territory includes: Northern California (East of Sacramento-Placer County and El Dorado County to Nevada and North along I-5) and the entire state of Nevada. Residence within the sales territory is required. What You'll Do Sell directly to niche market accounts to increase premium volume Retain profitable business by providing effective, quality service to policyholders Build and maintain quality relationships with businesses Work directly with Underwriting, Claims, Loss Control, Audit, Customer Service, and other key partners Call on and pursue all niche market opportunities assigned to your geographic territory Leverage current customers and relationships for new growth and sales opportunities What it Takes Bachelor's degree or equivalent work experience/related sales experience The ability to obtain and maintain the necessary P&C, and Life licenses required to sell the products Sentry offers Self-discipline and ability to thrive in a remote work environment Ability to multitask, prioritize, communicate effectively, and remain organized Strong analytical and math skills Acceptable Motor Vehicle Record with a valid driver's license and ability to meet travel requirements What You'll Receive At Sentry, your total rewards go beyond competitive compensation. Below are some benefits and perks that you'll receive. Company car with gas card Comprehensive, ongoing training, including licensure Laptop, cell phone reimbursement, home office setup Cutting edge proprietary technology that enables you to be more efficient and effective in the field 401(K) plan with a dollar for dollar match on your first eight percent, plus immediate vesting to help strengthen your financial future. Group Medical, Dental, Vision, Life Insurance, Parental Leave, and our Health and Wellness benefits to encourage a healthy lifestyle. Pretax Dependent Care and Health Expense Reimbursement Accounts to ease taxes on health spending. Well-being and Employee Assistance programs. Sentry Foundation gift matching program to encourage charitable giving. About Sentry Our bright future is built on a long track record of success. We got our start in 1904 and have been helping businesses succeed and protect their futures ever since. Because of the trust placed in us, we're one of the largest and financially strongest mutual insurance companies in the United States. We're rated A+ by A.M. Best, the industry's leading rating authority. Get ready to own your future at Sentry. Opportunities await! Casey Van Der Geest **************************** Equal Employment Opportunity Sentry is an Equal Opportunity Employer. It is our policy that there be no discrimination in employment based on race, color, national origin, religion, sex, disability, age, marital status, or sexual orientation.

The Director of Customer Service co-leads the strategic direction and daily operations of the customer service organization, ensuring exceptional customer experiences and operational excellence. This role is responsible for workforce management, process improvement, and cross-functional collaboration, driving measurable improvements in customer satisfaction and team performance. Key Responsibilities: * Accountable for delivery business outcomes and maintaining culture. * Develop and execute customer service strategies aligned with business objectives. * Oversee workforce management: staffing models, capacity planning, scheduling, and scenario modeling for multi-site, omni-channel environments. * Lead, mentor, and develop managers and representatives, fostering a culture of collaboration and continuous improvement. * Establish and monitor service level agreements, KPIs, and quality assurance programs. * Analyze operational outcomes and drive change for improved service delivery. * Collaborate with cross-functional leaders to ensure integrated processes and a unified customer experience. * Capture and analyze customer feedback, translating insights into actionable improvements. * Manage departmental budgets and resources efficiently. * Lead rapid response to service disruptions. Required Skills: * Workforce Management: Advanced expertise in workforce planning, scheduling, and optimization for large, multi-channel contact centers. * Customer Experience (CX): Deep understanding of customer lifecycle, journey mapping, and Voice of the Customer (VoC) programs. * Analytical Skills: Strong ability to analyze data, report on outcomes, and drive operational improvements. * Executive Communication: Excellent written and verbal communication, including executive storytelling and stakeholder engagement. * Change Management: Expertise in leading organizational change and process optimization. * Technology Proficiency: Familiarity with customer service platforms, workforce management systems, and analytics tools. Education & Experience: * Bachelor's degree in business administration or related field (MBA or advanced degree preferred). * Minimum of 10 years' experience in customer service, with at least 5 years in a senior leadership role and substantial workforce management responsibility. * Experience in Automated Quality Analytics, Voice Analytics, Integrated Voice Assistant, Telephony Optimization, Workforce Management and Next Best Action necessary. Salary Range: The pay range for this position is $131,000 to $190,500 annually. Actual compensation will vary based on multiple factors, including employee knowledge and experience, role scope, business needs, geographical location, and internal equity. Benefits & Perks: * Paid time off * Free onsite gym at our Boston location * Tuition reimbursement * Low cost and excellent health insurance coverage options that start on Day 1 (medical, dental, vision) * Robust health and wellness programs * Auto and home insurance discounts * Matching donation opportunities * Annual 401(k) employer contribution * Various Paid Family leave options including Paid Parental Leave * Resources to promote professional development * Convenient locations and pre-tax commuter benefits About the Company The Plymouth Rock Company and its affiliated group of companies write and manage over $2.4 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" #LI-PC1

We are seeking a proven self-motivated sales leader to guide a team of driven insurance sales professionals as a Region Manager within the Direct Writer segment of Sentry. You will play a vital role in driving success by managing a team of 6-8 sales professionals focused on commercial insurance, 401(k) plans, and life insurance. Your leadership will be crucial in developing and implementing plans that foster team success in sales, recruitment, customer retention and achieving financial goals. This is your chance to combine a rewarding career filled with success in our North Region including: Minnesota, North Dakota, South Dakota, and Nebraska. Residency within the territory is required. What You'll Do Develop, coach and travel with each of your team members to enhance sales skills that grows their book of business and maximizes their sales opportunities Recruit and train new members on your team, while providing leadership and encouraging high morale within your region Monitor, review and evaluate your team's development Manage expenses within your territory Maintain state licensing and engage in continuous learning to enhance knowledge and sales skills Assist your team with software programs and systems used in our sales process Prepare reports relating to production, loss ratios, etc. What it Takes Bachelor's degree or equivalent work experience 2+ years of related work experience, preferably leading a sales team Strong sales, communication and relationship building skills A self-disciplined individual that can thrive in a remote work environment Ability to multi-task, prioritize, communicate effectively both written and verbal, and remain organized Acceptable Motor Vehicle Record with a valid driver's license and able to meet travel requirements Required to have primary residence within your sales region Based on qualifications and experience, the starting base salary range is $88,900 - $122,200. When combined with incentive pay, and dependent on new and renewal business generated from the team by the territories in your region, this role may earn an estimated total annual income between $141,359-$229,659. What You'll Receive At Sentry, your total rewards go beyond competitive compensation. Below are some benefits and perks that you'll receive. Company car with gas card Laptop, cell phone reimbursement, home office setup, and more Continuous training and career development opportunities 401(K) plan with a dollar-for-dollar match on your first eight percent, plus immediate vesting to help strengthen your financial future. Generous Paid-Time Off plan for you to enjoy time out of the office as well as Volunteer-Time Off. Group Medical, Dental, Vision, Life Insurance, Parental Leave, and our Health and Wellness benefits to encourage a healthy lifestyle. Well-being and Employee Assistance programs. Sentry Foundation gift matching program to encourage charitable giving. About Sentry We take great pride in making Forbes' list of America's Best Midsize Employers. A lot of different factors go into that honor, many of which contribute to your job satisfaction. Our bright future is built on a long track record of success. We got our start in 1904 and have been helping businesses succeed and protect their futures ever since. Because of the trust placed in us, we're one of the largest and financially strongest mutual insurance companies in the United States. We're rated A+ by A.M. Best, the industry's leading rating authority. Our headquarters is in Stevens Point, Wisconsin, with offices located throughout the United States. From sales to claims, and information technology to marketing, we enjoy a rewarding and challenging work environment with opportunities for ongoing professional development and growth. Get ready to own your future at Sentry. Opportunities await! Casey Van Der Geest **************************** Equal Employment Opportunity Sentry is an Equal Opportunity Employer. It is our policy that there be no discrimination in employment based on race, color, national origin, religion, sex, disability, age, marital status, or sexual orientation.

We are currently seeking a risk control professional that is technically proficient, self-motivated and results driven to fill an open position within our West Region Shared Services division. The position will primarily provide safety and risk-management services to customers throughout California. You must be able to partner with our Underwriting teams to provide a strong analytical opinion of risk that supports our goal of profitable growth. In addition, the successful candidate will develop close relationships with our agents and policyholders, and provide value-added service to our customers. The ideal candidate's preferred location would be in the Los Angeles, Bakersfield or surrounding area. We are seeking a consultant who is passionate about consulting on safety and risk management practices, can work from home, and has excellent organizational skills to effectively manage their territory. Based on qualifications and experience, this position will be filled as a Risk Control Consultant I, II or Senior. Our pay range based on qualifications and experience for a Risk Control Consultant in the state of California is: $92,920 - $154,709.50 annually. What You'll Do The following are some of the responsibilities of the Risk Control Consultant position: Conduct onsite facility evaluations to determine if operational exposures are being adequately controlled to prevent building losses. Determine scope and schedule of preventative maintenance programs on key mechanical equipment within the facility (electrical systems, HVAC, machinery in use, and roof condition). Assist in determining if facility protections (fire suppression systems, alarm systems, etc.) are acceptable and appropriate for the building occupancy, exposures, and special hazards. Complete detailed reports for each covered line of business - Property, General Liability, Auto, & Workers Compensation, etc. - to assist our underwriting groups with account acceptability and insurability. Assist customers with development and implementation of safety polices, programs and procedures specific to each account & loss exposure. Provide advanced risk management and consultative services to assigned clients. Conduct Job-site safety inspections and OSHA 10-hour seminars for our Regional construction line of business. Maintain and demonstrate safety management and expertise in areas such as commercial property protection, general liability, product liability, fleet safety and employee safety. Develop, coordinate and conduct safety/risk management seminars and training programs for accounts to promote awareness and reduce claim frequency and severity. Develop and execute service proposals and plans to qualified accounts. What it Takes Bachelors degree within Safety is preferred or equivalent work experience Emphasis in Occupational Safety & Health, Engineering, or Physical Sciences preferred 1-5 years of insurance safety consulting or safety work in a private industry (construction and manufacturing) High level of independence, organization, and self-motivation to work from home Experience in coordinating and servicing large or multi location accounts preferred Knowledge of OSHA, ANSI, NFPA Standards, and DOT regulations High level of verbal and written communication skills Ability to learn use of specialized building valuation systems, diagramming and report software Acceptable motor vehicle record for travel (50%) including overnight travel in some cases Desire to pursue professionals Safety designations including CSP and/or other designations What You'll Receive At Sentry, your total rewards go beyond competitive compensation. Below are some benefits and perks that you'll receive. Generous Paid-Time Off plan for you to enjoy time out of the office. Company vehicle with gas card 401(K) plan with a dollar for dollar match on your first eight percent, plus immediate vesting to help strengthen your financial future. Group Medical, Dental, Vision and Life insurance to encourage a healthy lifestyle. Extensive Work-Life Resources to lend a helping hand. Sentry Foundation gift matching program to encourage charitable giving. Continue your education and career development through Sentry University (SentryU). About Sentry We take great pride in making Forbes' list of America's Best Midsize Employers. A lot of different factors go into that honor, many of which contribute to your job satisfaction. Our bright future is built on a long track record of success. We got our start in 1904 and have been helping businesses succeed and protect their futures ever since. Because of the trust placed in us, we're one of the largest and financially strongest mutual insurance companies in the United States. We're rated A+ by A.M. Best, the industry's leading rating authority. Our headquarters is in Stevens Point, Wisconsin, with offices located throughout the United States. From sales to claims, and information technology to marketing, we enjoy a rewarding and challenging work environment with opportunities for ongoing professional development and growth. Get ready to own your future at Sentry. Opportunities await! Esbeidy Guevara ************************** Equal Employment Opportunity Sentry is an Equal Opportunity Employer. It is our policy that there be no discrimination in employment based on race, color, national origin, religion, sex, disability, age, marital status, or sexual orientation.

As a Customer Service Associate, you will be responsible for delivering superior experiences to our customers by phone, email, and text. Specifically, these inquiries will be about our Auto Insurance product. You will use critical thinking skills and computer navigational abilities to solve customer problems in this dynamic, fast-paced environment. No two inquiries are ever the same, which makes this an exciting place to develop and hone your customer service and problem-solving skills. What is exciting about this role and Plymouth Rock? This is a salary-based position that comes with full benefits, and promotional opportunities. No prior insurance experience is required, as you will receive extensive, fully paid training and support. Plymouth Rock knows that happy employees promote happy customers, and that a successful, fulfilling employee experience makes all the difference. We foster a stable, diverse and thriving work environment where everyone feels valued, empowered and free to share ideas. Essential Functions & Responsibilities * Primary responsibility is to provide extraordinary service on all inquiries regarding our auto insurance product. These inquiries can come via phone, email, text and chat. * Making sure every customer interaction results in a great customer experience. * Develop and maintain strong knowledge of our revolutionary insurance product. * Accurately enter and update policy information into the various processing systems. * Build enduring relationships with agents, customers and team members. * Be willing to learn something new every day and apply it to future customer interactions. Qualifications and Education * Excellent oral and written communications skills * Bachelor's or Associate Degree preferred (or working towards a degree) * Ability to multitask and adapt to changes quickly * Capability to identify and address customer's needs to ensure an outstanding experience on every interaction * Capacity to work in a fast pace supporting the rapid growth of our customer base * Be a self-motivated individual to meet & exceed goals * Proficient in the use of Microsoft Office * Minimum of 1 year overall work experience preferred Salary Range: The pay range for this position is $45,000 to $50,500 annually. Actual compensation will vary based on multiple factors, including employee knowledge and experience, role scope, business needs, geographical location, and internal equity. Benefits & Perks: * Paid time off * Free onsite gym at our Boston location * Tuition reimbursement * Low cost and excellent health insurance coverage options that start on Day 1 (medical, dental, vision) * Robust health and wellness programs * Auto and home insurance discounts * Matching donation opportunities * Annual 401(k) employer contribution * Various Paid Family leave options including Paid Parental Leave * Resources to promote professional development * Convenient locations and pre-tax commuter benefits 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". #LI-DNI

Are you passionate about excellence and accuracy? Do you have a keen eye for detail and a drive to ensure the highest standards of quality? We are seeking a dedicated Quality Assurance Analyst to join our Home Underwriting Department. In this role, you will play a critical part in maintaining the integrity and reliability of our underwriting processes, helping us provide exceptional service for our customers and agents. Key Responsibilities * Perform comprehensive audits and quality reviews of home underwriting files to ensure compliance with internal guidelines, regulatory requirements, and industry best practices. * Execute targeted reviews of new underwriting initiatives related to both new business and renewal workflows. * Analyze underwriting decisions to identify trends, opportunities for process improvement, and training needs. This will involve collaborating to drive quality improvements and implement corrective actions. * Own the department's annual agency audit process to ensure compliance. * Document findings, prepare detailed reports, and communicate feedback to department leadership and key stakeholders. * Assist in the development and maintenance of quality assurance standards, policies, and procedures. * Monitor quality metrics and support the creation of dashboards and reporting tools. * Stay current with relevant laws, regulations, and underwriting requirements affecting home insurance. Qualifications * Bachelor's degree required. * 2+ years' experience in home underwriting, quality assurance, or related discipline. * Strong understanding of underwriting guidelines, regulations, and risk assessment. * Excellent analytical, problem-solving, and organizational skills. * Effective written and verbal communication skills, with the ability to present findings clearly and constructively. * Proficiency in Microsoft Office Suite (Word, Excel, PowerPoint). * Ability to work independently and as part of a collaborative team in a fast-paced environment. * High level of integrity, professionalism, and attention to detail. Salary Range: The pay range for this position is $60,000 to $81,500 annually. Actual compensation will vary based on multiple factors, including employee knowledge and experience, role scope, business needs, geographical location, and internal equity. Benefits & Perks: * Paid time off * Free onsite gym at our Boston location * Tuition reimbursement * Low cost and excellent health insurance coverage options that start on Day 1 (medical, dental, vision) * Robust health and wellness programs * Auto and home insurance discounts * Matching donation opportunities * Annual 401(k) employer contribution * Various Paid Family leave options including Paid Parental Leave * Resources to promote professional development * Convenient locations and pre-tax commuter benefits 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".

The Managing Attorney will be responsible for directing our House Counsel Offices in support of our Massachusetts and Connecticut litigation activities. He/She will balance managerial functions with the handling of a small caseload/back up support on pending cases. The Managing Attorney will maintain a thorough understanding of the business and its strategies to ensure sound legal counsel and advice in all matters affecting the business to maximize opportunities and mitigate risk and exposure. RESPONSIBILITIES * The managing attorney will direct staff attorneys and paralegals in the handling of litigated files to ensure compliance with best practices, provide guidance and direction, review and assign new cases, conduct internal quality reviews and work with claim leadership to ensure insureds receive a high quality defense and exceptional service. * Participates in the legal strategy of files handled by staff attorneys. Provides expertise by analyzing files and making decisions or recommendations in the areas of liability, damages, investigation, regulatory compliance, declaratory judgement actions and overall file handling. * Develops practices and procedures through reports and analytics to address quality, productivity, workflows and jurisdictional requirements. * Proactively assess legal risk and setting alternative dispute resolution strategies on warranted cases. * Prepare and analyze operational reports on all areas of the house counsel operation. * Continue to research case law, legislation and other court rules and processes that can affect the operation. * Manages and guide the development of the staff of the office to ensure they have the training, resources, feedback, and support to maximize their performance and skills development. * Actively engage with the General Counsel to manage the operations of the legal office and build and execute a strategic plan for the office. PERSONAL CHARACTERISTICS AND QUALIFICATIONS * Should possess a minimum of 15 years of related litigation experience in Massachusetts and preferably a minimum of 5-8 years of leadership experience. * Proven capability to negotiate complex situations; persuading others to take actions in a diplomatic and respectful manner. * Ability to respond effectively considering all perspectives to questions, concerns and issues. * Superior communication skills; collaborative with strong influencing and interpersonal skills. * Ability to function as a thought leader and proactive problem-solver in a dynamic fast paced environment. * Highest level of integrity and ethics, both professional and personal. * Experience with the Microsoft Suite (Excel, Power Point, Visio, Outlook etc…) * Data and analytical experience EDUCATION * Juris Doctor degree * Massachusetts Bar License Salary Range: The pay range for this position is $171,500 to $230,000 annually. Actual compensation will vary based on multiple factors, including employee knowledge and experience, role scope, business needs, geographical location, and internal equity. Benefits & Perks: * Paid time off * Free onsite gym at our Boston location * Tuition reimbursement * Low cost and excellent health insurance coverage options that start on Day 1 (medical, dental, vision) * Robust health and wellness programs * Auto and home insurance discounts * Matching donation opportunities * Annual 401(k) employer contribution * Various Paid Family leave options including Paid Parental Leave * Resources to promote professional development * Convenient locations and pre-tax commuter benefits 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"

We are looking for a versatile and creative Marketing Creative Specialist to join our Home Insurance Marketing team. This is a hybrid role that blends graphic design, digital content creation, light UX design, copywriting, and front-end support. You will play a key role in shaping customer, agent, and prospect experiences across multiple touchpoints-print, digital, web, and email. The ideal candidate thrives as a "creative problem-solver," someone comfortable wearing multiple hats and jumping in where needed-whether that's producing polished visuals, building creative assets, improving a landing page layout, or writing a compelling headline. This is a hybrid role with 1 day remote and 4 days in-office per week at our Boston, MA location. You'll join a collaborative, motivated marketing team that values creativity, accountability, and innovation. This role is perfect for a creative professional who enjoys variety, collaboration, and bringing ideas to life across channels. Responsibilities: * Creative Design & Production * Design and produce marketing materials including brochures, flyers, agent guides, and customer communications. * Develop visual assets for digital channels: social posts, emails, ads, and web elements. * Create and maintain templates and toolkits for broader team use. * Digital & UX Support * Support website and landing page updates via WordPress/Elementor. * Assist with email campaign visuals and content in Salesforce Marketing Cloud. * Apply UX best practices when designing web and digital experiences. * Collaboration & Strategy * Partner with marketing managers, developers, and other stakeholders to bring campaigns to life. * Contribute ideas in brainstorming and creative reviews. * Uphold and evolve brand standards across all creative outputs. * Content & Copywriting * Draft, edit, and proof short-form marketing copy (headlines, taglines, calls-to-action). * Collaborate with copywriters to refine messaging and ensure consistency of brand voice. Qualifications: * Education: Bachelor's degree in Graphic Design, Marketing, Communications, or related field. * Experience: 3-5 years in a creative marketing role (corporate, in-house, or agency). * Technical Skills: * Required: Adobe Creative Suite (InDesign, Illustrator, Photoshop), Microsoft Office (Word, PowerPoint, Outlook, Teams). * Preferred: Figma, WordPress (Elementor), Salesforce Marketing Cloud, basic HTML/CSS. * Strong understanding of design principles, content strategy, and brand consistency. * Ability to adapt tone and style across audiences and channels. * Portfolio required-demonstrating design versatility, digital work, and creative problem-solving. * Excellent project management skills and ability to juggle multiple deadlines. * Collaborative, flexible, and resourceful mindset. How to Apply: Please submit your resume with a link to your portfolio (including design and digital work). Applications without a portfolio will not be considered. Salary Range: The pay range for this position is $68,500 to $91,000 annually. Actual compensation will vary based on multiple factors, including employee knowledge and experience, role scope, business needs, geographical location, and internal equity. Benefits & Perks: * Paid time off * Free onsite gym at our Boston location * Tuition reimbursement * Low cost and excellent health insurance coverage options that start on Day 1 (medical, dental, vision) * Robust health and wellness programs * Auto and home insurance discounts * Matching donation opportunities * Annual 401(k) employer contribution * Various Paid Family leave options including Paid Parental Leave * Resources to promote professional development * Convenient locations and pre-tax commuter benefits 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". #LI-SK1

We are seeking a visionary Head of Artificial Intelligence to drive new strategic AI initiatives across Plymouth Rock. In this leadership role, you will conceive and help oversee AI initiatives across the organization, collaborating with cross-functional teams to deliver innovative, cutting-edge solutions. The ideal candidate will combine deep expertise in artificial intelligence with strong strategic vision, exceptional communicative and persuasive skills, and an ability to lead transformative projects from inception to execution. An advanced degree (Master's or Ph.D.) in Computer Science, Engineering, Data Science, or a related field, is required. Unusually high levels of energy, motivation, and determination are also required. Prior business experience is useful but not required. In this role, you will: * Propose AI strategies that align with the company's overall business objectives and identify opportunities where AI can drive innovation, efficiency, and business transformation. * Stay ahead of AI industry trends and emerging technologies. * Collaborate with senior executives, department heads, and cross-functional teams to align AI initiatives with company goals. * Identify and manage relationships with external AI vendors, research institutions, and strategic partners and help negotiate contracts and manage third-party AI collaborations. We enthusiastically welcome applications from recent Ph.D. graduates who have demonstrated AI expertise and research excellence, even if you do not yet have extensive business or industry experience. Salary Range: The pay range for this position is $233,500 to $321,000 annually. Actual compensation will vary based on multiple factors, including employee knowledge and experience, role scope, business needs, geographical location, and internal equity. Benefits & Perks: * Paid time off * Free onsite gym at our Boston location * Tuition reimbursement * Low cost and excellent health insurance coverage options that start on Day 1 (medical, dental, vision) * Robust health and wellness programs * Auto and home insurance discounts * Matching donation opportunities * Annual 401(k) employer contribution * Various Paid Family leave options including Paid Parental Leave * Resources to promote professional development * Convenient locations and pre-tax commuter benefits About Plymouth Rock Founded in 1982 and headquartered in Boston, writing approximately $2.5 billion in annual premiums, Plymouth Rock is a privately held insurer specializing in automobile and home insurance. Plymouth Rock considers itself to be the "largest of the entrepreneurial insurers" and the "smallest of the large insurers." We blend the agility, innovation, and growth potential of a dynamic startup with the resources, stability, and security of a well-established organization. We offer the right candidate: * An opportunity to spur transformative AI initiatives working with talented professionals. * An ambitious, flexible, collegial, and family-friendly workplace. * A competitive salary with excellent benefits and ancillary perquisites. #LI-DNI

In this position, the Team Lead will be responsible for interpreting insured and agency analytics, work collaboratively across the organization, execute processes to identify and address Rate Evasion, identify potential areas of risk and work internally with Claims, Sales, Product and Customer Care and directly with insured and agencies to resolve findings. At all times represent the brand, deliver Six Sigma results while maintaining the highest level of customer experience. This role will be focused on Massachusetts state results and responsibilities that extend across New England and New York. To meet the needs of our organizations and the clients we services your role may be asked to support Customer Care inquiries, Endorsement processing, quoting and any other activities that will support the organizations success. Further, the Team Lead will have responsibility in overseeing Customer Care general support, including but not limited to supporting endorsements as well as monitoring service level. Responsibilities * Become a knowledge resource for state regulator requirements, the firm's products and underwriting guidelines and philosophy. * Maintain documentation of department procedures. * Provide feedback and input into potential process improvements. * Deliver timely and accurate progress reports and monthly business results as required. * Execute and maintain a repeatable Rate Pursuit analytical process that evaluates insured's and our agency force. * Constantly and consistently evaluate methods that will enable the firm to maximize premium collection. * Be available and approachable and thoughtfully address escalated issues, complaints, questions and inquiries. * Execute multiple Rate Pursuit, New Business and Renewal projects. This may include home inspections, new business policies, umbrella renewal questionnaires, driver discovery, questionable risk referrals and garaging analysis. * Work closely with the Claims department to evaluate trends and take appropriate Underwriting action. * Be the lead trainer for new underwriting associates and maintain all training procedures * Be responsible for quality assurance checks of the teams tasks and report to supervisor * Function in leadership capacity when management is unavailable * Capable of working independently with minimal supervision * Serve as point of contact for Marketing and collaborate on positioning agencies * Assess team for training opportunities and development needs to ensure opportunity of growth * Set a professional example in both approach and work ethic * Special projects as assigned * Some travel will be required Knowledge, Skills, and Abilities Required: * Experience in analyzing and interpreting qualitative and quantitative data/results. * Excellent organizational and communication skills. * Exceptional analytical, critical thinking and problem solving skills. * Strong knowledge of customer care techniques and processes. * Excellent written and oral communication skills. * Ability to multitask. * Sound knowledge of Microsoft Office with good - excellent EXCEL skills Education & Experience: * The ideal candidate will possess 4-6 years of relevant underwriting experience. * Personal Lines Auto and Home experience preferred. * P&C Licensed Salary Range: The pay range for this position is $68,500 to $109,000 annually. Actual compensation will vary based on multiple factors, including employee knowledge and experience, role scope, business needs, geographical location, and internal equity. Benefits & Perks: * Paid time off * Free onsite gym at our Boston location * Tuition reimbursement * Low cost and excellent health insurance coverage options that start on Day 1 (medical, dental, vision) * Robust health and wellness programs * Auto and home insurance discounts * Matching donation opportunities * Annual 401(k) employer contribution * Various Paid Family leave options including Paid Parental Leave * Resources to promote professional development * Convenient locations and pre-tax commuter benefits 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".

The Plymouth Rock Home team is an Insurtech start-up within a well-established insurance company. We tripled our topline revenue over the past 4 years by revolutionizing the way homeowners insurance is marketed, bought, and sold, enabling customers to obtain a home insurance quote in just seconds. Our @home product marries cutting edge data science and predictive modeling with a simplified sales process and a feature-rich package that our distributors want to sell and consumers want to buy to protect the things they value most. About the Role We are seeking a highly motivated and technically skilled Lead Data Scientist to join our fast-paced, entrepreneurial team. This role is a unique opportunity for a seasoned data scientist who thrives on independence, wants to be deeply embedded in the business, and is passionate about using data to drive real-world outcomes. In this role, you won't just build models-you'll own them. Reporting directly to the VP of Product, you'll translate business needs into analytical frameworks, lead the design and deployment of full-stack predictive models, and influence pricing and underwriting strategy in a growing business. You will be embedded on the Product team, collaborate directly with senior leadership, and make regular presentations to the CEO. You'll be the analytics powerhouse behind the team's pricing and underwriting sophistication-pushing the boundaries of segmentation and innovation in a highly visible and impact-driven capacity. There is an opportunity to bring your deep expertise in data science and passion for innovation driving results to this role. What You'll Do * Own the end-to-end predictive modeling process, from business problem definition and data acquisition to deployment and performance monitoring. * Collaborate directly with business leaders, product owners, and cross-functional stakeholders to align modeling strategies with business goals. * Translate complex modeling results into actionable insights for technical and non-technical audiences alike. * Work hands-on with large insurance datasets to uncover pricing and segmentation opportunities. * Lead the discovery, evaluation, and incorporation of new data sources and methods, including third-party vendor collaborations. * Monitor model performance, perform root-cause analysis, and iterate on solutions to enhance business outcomes. * Champion best practices in coding, reproducibility, and documentation using modern analytics infrastructure. * Incorporate Artificial Intelligence into your daily work to drive innovation, insights, and speed-to-market. What You Bring * Proven ability to work independently, owning the entire modeling lifecycle. * Fluency in Python (preferred) and R, including experience with production-ready modeling code and analytical pipelines. * Expert-level SQL skills for large-scale data transformation and aggregation. * Solid experience with cloud computing tools (especially AWS: S3, EC2, SageMaker) and Snowflake. * Mastery of GLMs and GBMs (e.g., H2O, XGBoost, LightGBM); familiarity with clustering, Bayesian inference, regularization, and optimization a plus. * Comfort working within Git-based, version-controlled environments. * Strong grasp of relational databases and experience working with large, multi-source insurance datasets. * Excellent communication skills, with experience presenting complex findings to senior executives. * Master's or PhD in a quantitative field (e.g., STEM, Economics) strongly preferred. * Prior knowledge of homeowners insurance and/or pricing frameworks is a plus. Bonus Points * Experience with tiering logic and segmentation beyond core risk pricing. * Exposure to regulatory concerns regarding insurance pricing models and variable selection. * Expertise in data visualization using tools like Plotly and Seaborn. * Experience collaborating with non-technical stakeholders to drive decision-making. * Experience using Artificial Intelligence tools both in super-charging your work and delivering results for the business. Why This Role is Unique * High Visibility: Present directly to the CEO and reports directly to the VP of Product who owns the business P&L. * Strategic Impact: See the direct business value of your models in premium growth, profitability improvements, pricing decisions, and underwriting strategy. * Full-Stack Autonomy: You manage everything-data wrangling, feature engineering, model training, deployment, and monitoring. * Embedded with Product: You're not a service function-you're part of the business team, with aligned incentives and shared goals. * Innovative Environment: Use custom modeling frameworks to test new ideas in an agile, responsive, and entrepreneurial setting. Salary Range: The pay range for this position is $153,500 to $204,000 annually. Actual compensation will vary based on multiple factors, including employee knowledge and experience, role scope, business needs, geographical location, and internal equity. Benefits & Perks: * Paid time off * Free onsite gym at our Boston location * Tuition reimbursement * Low cost and excellent health insurance coverage options that start on Day 1 (medical, dental, vision) * Robust health and wellness programs * Auto and home insurance discounts * Matching donation opportunities * Annual 401(k) employer contribution * Various Paid Family leave options including Paid Parental Leave * Resources to promote professional development * Convenient locations and pre-tax commuter benefits About the Company The Plymouth Rock Company and its affiliated group of companies write and manage over $2.5 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 2,000 people and is headquartered in Boston, Massachusetts. Plymouth Rock Assurance Corporation holds an A.M. Best rating of "A-/Excellent". #LI-PC1

We are seeking a highly motivated and experienced Analytics Manager to lead our P&C Claims analytics team. This critical role will be responsible for transforming our claims organization from a reactive reporting environment to a proactive, insights-driven powerhouse. The ideal candidate will have a deep understanding of P&C claims data, strong analytical skills, and proven leadership abilities. This individual will manage a team of analysts, drive deep and actionable analysis, develop predictive models, and collaborate with key stakeholders across the organization to drive strategic decision-making. Responsibilities: * Lead and mentor a team of claims analytics and professionals of varying experience levels. * Oversee all areas of claims analysis, including claims efficiency, operational metrics analysis, actuarial-claims analysis, and data science efforts. * Develop and implement a strategic vision for claims analytics, moving the organization from reactive reporting to proactive insights. * Analyze claims operational metrics, linking results to broader performance on both a micro (by coverage) and macro (overall claims loss ratio/expense ratio) level. * Develop and own predictive models to support claims management, reserving, and other key functions. * Collaborate closely with Claims and Actuarial leadership to understand their needs and deliver impactful analyses. * Prioritize and manage a high volume of requests from multiple stakeholders, ensuring that the team's analytical efforts are focused on the most critical initiatives. * Present findings and recommendations to senior management in a clear and concise manner. Qualifications: * Bachelor's degree in a quantitative field (e.g., statistics, business, mathematics, etc.). Master's degree preferred but not required. * Extensive experience in analytics within the P&C insurance industry, preferably personal lines auto analytics. * Deep expertise in SQL, Excel, and Tableau. Proficiency in R or Python is a plus. * Proven ability to manage and mentor a team of analysts. * Strong analytical, problem-solving, and communication skills. * Ability to work independently and manage multiple projects simultaneously. Salary Range: The pay range for this position is $137,500 to $184,000 annually. Actual compensation will vary based on multiple factors, including employee knowledge and experience, role scope, business needs, geographical location, and internal equity. Benefits & Perks: * Paid time off * Free onsite gym at our Boston location * Tuition reimbursement * Low cost and excellent health insurance coverage options that start on Day 1 (medical, dental, vision) * Robust health and wellness programs * Auto and home insurance discounts * Matching donation opportunities * Annual 401(k) employer contribution * Various Paid Family leave options including Paid Parental Leave * Resources to promote professional development * Convenient locations and pre-tax commuter benefits 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" #LI-DNI

The Product Analyst will play a key role in shaping the company's product strategy, pricing, and competitive positioning across P&C insurance lines. In this role, you will support favorable business outcomes by analyzing complex issues and providing actionable recommendations for rating plans, underwriting rules, process enhancements, and other strategic initiatives. You will also serve as a bridge between the Product department and other functions, including Underwriting, Marketing, Finance, and Technology. Responsibilities: * Contribute to the management of P&C product performance, supporting profitable growth and achievement of business targets. * Conduct quantitative analyses to inform pricing, underwriting, and product strategies, leveraging predictive modeling concepts and other advanced techniques. * Identify trends, develop hypotheses, and proactively recommend solutions to business challenges. * Manage and support projects of moderate to high complexity, using data systems and analytical tools to diagnose issues, test solutions, and deliver insights to leadership. * Collaborate cross-functionally to ensure product strategies are aligned with business needs and market opportunities. * Monitor competitor actions, regulatory developments, and market trends in assigned states to identify risks and opportunities, and recommend strategic responses. Requirements: * Understanding of and experience with insurance products and operations, including underwriting/claims, pricing/rating concepts, insurance finance and risk selection methodologies. Commercial Auto experience desired but not required. * 3 or more years in product management, underwriting, claims, or other analytical role. * 3 or more years of experience with relational database tools and concepts. Proficiency with data extraction, manipulation, analysis, presentation and programming query tools (MS-SQL preferred). * Strong strategic thinking skills and structured problem-solving ability developing and implementing new, creative and effective solutions to highly complex business issues. * Confidence in taking ownership of challenging business issues, experience managing multiple projects and making decisions with limited or incomplete data and seeing issues through to resolution. * Ability to communicate effectively to both technical and non-technical audiences. * Ability to establish and build productive working relationships internally and externally, lead mentoring relationships (as needed), and negotiate. * Bachelors or higher level degree preferred * CPCU or other professional insurance designation(s) desired but not required. Salary Range: The pay range for this position is $66,000 to $85,000 annually. Actual compensation will vary based on multiple factors, including employee knowledge and experience, role scope, business needs, geographical location, and internal equity. Benefits & Perks: * Paid time off * Free onsite gym at our Boston location * Tuition reimbursement * Low cost and excellent health insurance coverage options that start on Day 1 (medical, dental, vision) * Robust health and wellness programs * Auto and home insurance discounts * Matching donation opportunities * Annual 401(k) employer contribution * Various Paid Family leave options including Paid Parental Leave * Resources to promote professional development * Convenient locations and pre-tax commuter benefits About the Company The Plymouth Rock Company and its affiliated group of companies write and manage over $2.2 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 2,000 people and is headquartered in Boston, Massachusetts. Plymouth Rock Assurance Corporation holds an AM Best rating of "A-/Excellent." #LI-SK1

The Underwriting Serivces Representative will support the Commercial Auto Underwriting team through extraordinary customer service, attentive underwriting review, and efficient transaction processing. The ideal candidate must have an analytical mind and will work with the team to provide timely, courteous and efficient service. This position requires excellent written and verbal communication skills. Knowledge of Commercial Auto coverages and rating is preferred. Responsibilities * Provide extraordinary service to our policy holders and agents, promptly answering inquiries on policies, coverages and premiums; take ownership for thorough follow-up, completion or escalation of all tasks. * Utilize the company's various systems and procedures to provide knowledgeable and professional customer service on inquiries regarding billing and underwriting of Commercial Auto accounts. Elevate issues as needed. * Process data entry and clerical duties, ensuring transactions are completed accurately and efficiently in compliance with established procedures and to maintain productive time service standards. Transactions include quote rating, new business, policy changes, renewals, cancellations, and running of reports to support team underwriting review. * Analyze transactions efficiently and with strong attention to detail to evaluate underwriting acceptability and to determine proper processing. Gather required detail for analysis and processing, also utilizing third party data. * Develop and foster Agent/Company relationships through reliable performance and effective communication that is delivered clearly and with considerate service. * Manage time efficiently and handle multiple tasks in a fast-paced work environment. * Assist team members with projects as needed in a timely fashion. * Maintain a positive demeanor and work well in a team environment. Requirements * College degree or equivalent experience in an insurance position * Minimum of 2 years customer service, processing or related work experience * Excellent computer/data entry and processing skills * Strong analytical, critical thinking and decision-making skills * Excellent verbal and written communication skills * Very detail-oriented and strong self-motivating individual with excellent organizational skills, the ability to work independently to prioritize dynamic responsibilities, as well as to multitask and collaborate well in a team environment * Working knowledge of Microsoft Office products * Experience in automobile insurance including knowledge of commercial automobile products and rating preferred Perks and Benefits * Paid time off * Free onsite gym at our Boston location * Tuition reimbursement * Low cost and excellent health insurance coverage options that start on Day 1 (medical, dental, vision) * Robust health and wellness programs * Auto and home insurance discounts * Matching donation opportunities * Annual 401(k) employer contribution * Various Paid Family leave options including Paid Parental Leave * Resources to promote professional development * Convenient locations and pre-tax commuter benefits Salary Range: $46,000 - $60,000 a year. Actual compensation will vary based on multiple factors, including employee knowledge and experience, role scope, business needs, geographical location, and internal equity. 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". #LI-RJ1

The Boston-based Home Product team is seeking a self-motivated and creative intern with a strong desire to leverage their analytical skills to help solve practical business problems. Responsibilities * Gain valuable business knowledge in a fast-paced insurance industry through hands-on training and onboarding * Leverage quantitative and qualitative data to perform business analyses to identify, test, and inform critical business decisions * Evaluate the company's competitive position through research and analysis of competitive intelligence reports * Assist with developing business and underwriting strategies * Work independently as well as collaborate with and learn from team members on various projects * Participate in cross-functional project team representing Product * Have opportunities to present to senior management Qualifications * Currently enrolled in a Bachelor's or Master's program in a Business, Economics, Mathematics, Statistics, Actuarial Science, or related field * Prior Insurance or Casualty Experienced preferred * Strong problem-solving skills * Excellent verbal and written communication skills * High level of intellectual curiosity * Previous co-op/internship experience preferred * Some knowledge of data analytics tools - Excel, preferably including SQL, R, or Python Salary Range: The pay range for this position is $25 to $30 per hour. Actual compensation will vary based on multiple factors, including employee knowledge and experience, role scope, business needs, geographical location, and internal equity. 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"

We're seeking an Associate UX Designer to join our User Experience team. This entry-level role offers a unique opportunity to contribute to human-centered design across a range of digital products and services. The ideal candidate will support UX research and design activities, including conducting user interviews, synthesizing qualitative and quantitative data, and translating insights into actionable design solutions. You'll work closely with senior UX teammates, developers, business analysts and product managers to craft intuitive, accessible, and engaging user experiences. Essential role functions and responsibilities include: Design Development * Develop wireframes, prototypes, and user flows based on research findings and design requirements. * Iterate on design solutions based on feedback from stakeholders, usability testing, and design reviews. * Create visual assets, including icons, buttons, and other UI components, ensuring consistency with design guidelines and brand standards. User Research and Analysis * Assist in conducting user interviews, surveys, and usability tests to gather insights about user needs and behaviors. * Help analyze research data and translate it into actionable design insights. Collaborate with researchers to identify user pain points and opportunities. Collaboration and Communication * Collaborate with product managers, developers, and other team members to ensure designs are feasible and aligned with project goals. * Present design concepts and solutions in design reviews, incorporating feedback from senior designers and stakeholders. * Assist in facilitating design workshops and brainstorming sessions to generate ideas and solve design problems. Design Documentation and QA * Help create, maintain, and update design systems, style guides, and component libraries to ensure consistency across products. * Document design processes, decisions, and rationale to ensure clarity and transparency for team members. * Participate in usability testing sessions to evaluate design effectiveness and identify areas for improvement. Continuous Learning and Improvement * Keep up with the latest design trends, tools, and best practices to continuously improve design skills and methodologies. * Actively seek feedback from senior designers and other team members to grow professionally and improve design capabilities. Qualifications and Experience: * Bachelor's degree in Design, HCI, or a related field. * 1 to 3 years of experience through internships, freelance work, or personal projects. * Proficiency in design tools such as Figma and Adobe. * Strong communication skills and attention to detail. * Familiarity with user research methods and usability testing. * Basic understanding of HTML/CSS is a plus. * Knowledge of accessibility best practices. Perks and Benefits * 4 weeks accrued paid time off + 9 paid national holidays per year * Free onsite gym at our Boston Location * Tuition Reimbursement * Low cost and excellent coverage health insurance options that start on Day 1 (medical, dental, vision) * 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 * Resources to promote Professional Development (LinkedIn Learning and licensure assistance) * Convenient location directly across from South Station and Pre-Tax Commuter Benefits Salary Range: $74,500-$100,000 a year. Actual compensation will vary based on multiple factors, including employee knowledge and experience, role scope, business needs, geographical location, and internal equity. About the Company The Plymouth Rock Company and its affiliated group of companies write and manage over $2.2 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 2,000 people and is headquartered in Boston, Massachusetts. Plymouth Rock Assurance Corporation holds an A.M. Best rating of "A-/Excellent". #LI-DNI

Plymouth Rock is looking for energetic, driven entry-level candidates to work in their Claims Department. The primary responsibility of this role is to handle property and casualty claims. Working in our downtown Boston location (across the street from South Station), Claims Representatives investigate, evaluate and create a disposition of the first and third party auto property damage claims. Plymouth Rock offers competitive salaries and top notch benefits including dental and vision insurance as well as a 401k company match. We have a Boston Sports Club in our building and also offer extensive training to start help jumpstart your career. Job Description The Sr. Network Engineer will be supporting a Cisco based network infrastructure with 11 office locations in the Northeast with two Data Centers providing connectivity to over 750 physical and virtual servers. We are specifically looking for someone with advanced experience: implementing, programming, and troubleshooting network hardware/software including: routers, switches, wireless access points, load balancers, network monitoring, remote access, VPN's, and firewalls. Our current WAN environment incorporates the use of routing protocols OSPF and BGP over Ethernet Private Line (EPL), Dedicated, and Broadband Internet carrier services. Job Responsibilities: Maintain a complex wired and wireless network infrastructure supporting distributed business applications as well as E-Commerce, VoIP, and video Design, maintain, and manage an enterprise-wide network infrastructure hierarchy Develop and document system standards for computer and network devices Create and update documentation of the networking environment including inventory of equipment as well as documentation of vendor activities Develop implementation plans, test plans, and project timelines for various network projects Maintain knowledge of network environment in conjunction with business applications and systems Actively monitor LAN/WAN network traffic and capacity maximizing available software reporting tools Proactively evaluate network performance and utilization trends Troubleshoot and analyze network communication failures and congestion Help resolve production problems in a large-scale environment impacted by a network issue Escalate network carrier issues as necessary Generate vendor quotes for network hardware, software, and support contracts Ensure the development and use of an effective preventive maintenance program suitable to meet the operation objective of "99.9% availability" Respond to all system problems on a 7 by 24 basis and take part in on-call rotation Attend seminars and training to maintain proficiency with latest network technologies Perform other job-related duties as assigned including helping telephony team with Avaya Communications Manager voice support Qualifications BS/MS (CS/EE preferred), Advanced Degree a plus Minimum Cisco Certification CCNP Demonstrated experience with multiple Cisco network product suites including: ISR routers (4451, 38XX, & 28XX), ASR router 1001; Nexus 9XXX switches and Catalyst switches (65XX, 45XX, 35XX & 29XX); and ASA 55XX firewalls Familiarity with Cisco Wireless Controllers and Access Points 5 plus years of design and implementation experience of routing and switching with Cisco hardware/software including L1/L2/L3 design principles Experience working with OSPF routing protocol 5 plus years of hands-on networking experience in a mission-critical production environment of 750+ servers using Microsoft Windows and Linux based technologies Knowledge and understanding of RADIUS Server/Authentication Experience with Cisco and Juniper firewalls desired, including hardware and software upgrades, migrations, rule additions, NATs, routing, and troubleshooting. Knowledge of load balancing technologies including installation, software upgrades, building VIP's, error handling, and L4 concepts. Experience with Netscaler desired and Radware App Director experience a plus Design/troubleshooting of spanning tree, routing protocols, IP network address subnetting and NATs Hands-on experience with enterprise-grade network monitoring systems and knowledge of Solarwinds platform a plus Experience using WAN technologies, circuit technologies like EPL, T1, and WAN routing protocols such as MPLS and BGP Ability to perform packet level analysis with network protocol analyzer software tools Experience using Internet and networking technologies such as DNS, DHCP, SMTP, SNMP, & NTP Expertise with QoS network prioritization desired Strong communication skills - oral and written Additional Information All your information will be kept confidential according to EEO guidelines.