The Plymouth Rock Company Incorporated jobs - 55 jobs

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".

Our highly trained Account Executives present specialized commercial insurance, 401K, and life insurance products that are perfectly designed for the industries we serve. 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. 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 $196,870-$232,870, 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 Texas territory includes: the greater Austin area. 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.

As a Risk Control Consultant-Hortica team you will conduct onsite risk evaluation surveys & complete detailed reports to assist our Underwriting groups with account acceptability. At Hortica, we believe people are our competitive advantage. We strive to attract, train and motivate our employees to keep Hortica as a market leader in our industry. We are committed to hiring people with the potential to excel. As a brand of the Sentry Insurance Group, we are the insurance specialists for the horticultural industry in America. Based on qualifications and experience, this position can be filled as a Risk Control Consultant I or a Risk Control Consultant II. The base salary range for a Risk Control Consultant I is: $68,100-$102,100 The base salary range for a Risk Control Consultant II is: $82,400-$123,600 What You'll Do The ideal Risk Control Consultant will be located in the Austin, TX area and be able to conduct onsite safety and risk assessments and training to our business insurance customers. Core service states are Texas, Florida, Alabama and Oklahoma. Additional service states include Arkansas, Kansas, Mississippi, Louisiana. Additionally, you'll: Provide risk management and consultative services to businesses by developing and implementing safety polices, programs and procedures specific to each account. Develop and demonstrate safety management expertise in areas such as commercial property protection, employee safety, product and employment liability and vehicle safety. Develop, coordinate and conduct safety/risk management training programs for accounts to promote awareness and reduce claim frequency and severity. Develop and execute service proposals and plans to large accounts. What it Takes Four-year degree within Safety Sciences is preferred, or equivalent work experience Bilingual in Spanish required Experience working in Horticulture/greenhouse farming setting (growing crops and vegetables in a greenhouse), and/or knowledge of produce food safety practices - GAP, GMP, GFSI, etc. a plus Emphasis in Occupational Safety & Health, Engineering, or Physical Sciences preferred 2-5 years of insurance safety consulting preferred Knowledge of OSHA, DOT, FSMA, and EPA pesticide regulations High level of independence, organization, and self-motivation to work from home Ability to coordinate and service large accounts with multi location operations Familiarity with occupational safety and fire protection standards or regulations High level of verbal and written communication skills Acceptable motor vehicle record Ability to travel overnight up to 50% of the time 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! 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.

In this role you will be handling the field adjustment and management of homeowners property claims over North Shore, MA (Wakefield, Methuen, Somerville) The Associate Field Claims Representative is responsible for investigating and evaluating homeowners claims by conducting on-site inspections at insured locations. This role requires daily travel to policyholders' homes to assess damages, gather documentation, and determine coverage in accordance with company guidelines. While the exact radius of travel will vary, we expect you to be able to travel one to two hours from home on a daily basis. Responsibilities: * Conducting accurate coverage analysis and damage assessments to ensure prompt payment of claims in accordance with quality standards * Proactive communication, and setting accurate claims length expectations * Writing estimates for covered damage, provide customers scope of loss and cost of repairs * Assign, direct and oversee vendors conducting mitigation and/or inspection during the adjustment of homeowners' property claim * Identify subrogation potential and liability exposures * Establish timely and appropriate claim reserves in accordance with claim standards * Adjusting homeowner's property claims in all states in which Plymouth Rock writes business. * Appropriately represent the company by executing a high level of service and maintaining professionalism at all times Qualifications: * Mitigation, Remediation, Construction, or Insurance background is preferred but not required * 1 to 3 years of Homeowners Claims Experience * Xactimate experience preferred * Bachelor's Degree from an accredited four-year college or university is preferred * Excellent oral and written communications skills * 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 * Ability to obtain licensure in applicable states if required and complete CE credit/classes where necessary * Ability to carry up to 25lbs and conduct roof inspections on homes * Valid Driver's License and proficient driving record 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) * Remote work equipment Salary Range: $47,000 - $63,000 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-SM1

We're looking for a Salesforce Marketing Cloud Manager to lead the strategy and execution of our Salesforce Marketing Cloud platform. As both a Technical Owner and Digital Product Manager, you will shape the roadmap, own platform optimization, and drive customer engagement through personalized, data-driven communication. You'll be at the intersection of technology, marketing, and innovation-helping us elevate our digital experience and drive measurable results. Essential Functions and Responsibilities: Platform Ownership * Lead the administration, configuration, and optimization of Salesforce Marketing Cloud (SFMC). * Architect solutions across SFMC modules (Journey Builder, Mobile Studio, Cloud Pages, etc.) for email, SMS, and mobile campaigns. * Oversee system integrations, data structure, AMPscript and SSJS scripting, and API use cases. * Maintain compliance with digital communication regulations (CAN-SPAM, TCPA). Drive Strategy * Serve as the Product Owner for SFMC-manage the vision, roadmap, and backlog to align with broader marketing and business goals. * Collaborate with stakeholders to turn customer insights into automation strategies that drive acquisition, retention, and conversion. Lead and Collaborate * Manage and mentor a team of Marketing Cloud Developers - fostering professional growth and technical excellence. * Partner with cross-functional teams in Marketing, IT, and Analytics to deliver seamless digital experiences. Execute High-Impact Campaigns * Design and launch multichannel customer journeys using automation tools and advanced data segmentation tactics. * Run A/B tests and optimize performance using tools like Einstein Recommendations, analytics, and personalization features. Measure and Optimize * Build dashboards and reports to track KPIs-such as open rates, click-through rates, and conversion performance. * Use insights and root cause analysis to drive continuous improvement and marketing efficiency. Innovate * Stay ahead of industry trends, emerging technologies, and platform enhancements. * Identify new opportunities to enhance customer experience and improve ROI. * Bring artificial intelligence into the day-to-day workflow to further improve team outcomes. Qualifications and Education: * 5+ years of hands-on experience with Salesforce Marketing Cloud (including Journey Builder, Mobile Studio, Automation Studio). * Strong working knowledge of AMPscript, SQL, SSJS, and APIs. * Proven success managing end-to-end marketing automation strategy and execution. * Bachelor's degree in Marketing, Computer Science, Information Technology, or related field. * Strong project management skills and ability to lead in a fast-paced environment. * Experience using Jira to manage backlogs and organize work. * Ability to communicate complex technical topics to business stakeholders. * Experience with Salesforce Data Cloud and Agentforce is a plus. * Salesforce Marketing Cloud Certifications are preferred. 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: $122,000-$170,000 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".

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

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

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"

Markets companies' products and services to assigned Commercial Lines accounts and independent agencies and underwrite with those partners. What You'll Do The Territory Underwriting Specialist will be responsible for agent and broker relationships. The ideal candidate will work from home and reside in Wisconsin. As a Territory Underwriting Specialist, you will: Solicit accounts through select agents and brokers Evaluate, underwrite, and price prospective accounts to select independent agents Serve as the primary contact with assigned agents and brokers Provide comprehensive sales expertise to increase production through agency channels Work with assigned agents and brokers on the coordinating of resolutions In addition, you will: Solicit accounts through appointed commercial lines independent agents and/or selected agents/brokers, or in response to inquiries from prospective clients, or referrals. You will be tasked with prospecting potential new agencies and the related items such as coordinating agency appointments, agency evaluation/review and overseeing agency activity. Analyze quality and quantity of risks underwritten and manages a book of business within their current authority levels. Initiate and implement market development programs designed to support and enhance market segmentation, penetration, sales and profitability. Evaluates prospective accounts and independent agencies to determine their acceptability and works closely with management, Underwriting, Loss Control and Claims in determination of acceptability of the risk and the services needed. Serves as primary contact with assigned accounts and agencies. Provide service to and work in conjunction with the functional units of Loss Control, Claims and Operations to provide that service. Develop and maintain relationship/services, procedures and contacts for assigned business products accounts and agencies. Provide comprehensive sales expertise to independent agencies to increase production. Develop rapport with agents to develop acceptable and profitable business. Assist in development of premium goals by agency and monitor agency results. Promote Sentry products and services to existing and potential customers. Travel and have a valid driver's license with the ability to maintain an acceptable motor vehicle record. Mileage reimbursement for all work-related local travel using your personal vehicle. What it Takes Bachelor's degree or equivalent work experience Minimum of 5 years of related work experience required with multi-line middle market underwriting experience handling accounts in construction, manufacturing, wholesale, real estate, and service industries preferred Knowledge of the Wisconsin middle market property and casualty insurance marketplace, existing or past relationships with larger independent agents preferred Previous technical insurance experience, preferably with sales Experience with underwriting large complex accounts Exceptional communication and relationship building skills Strong business and pipeline development skills Ability to meet travel requirements as you'll be prospecting new business opportunities in an agent office; meeting with insureds during safety inspections, and participating in mid-year claims review meetings 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. As a work from home associate, Sentry will provide equipment for your home office. 401(K) plan with a dollar for dollar match on your first eight percent, plus immediate vesting to help strengthen your financial future. Continue your education and career development through Sentry University (SentryU) and utilize our Tuition Reimbursement program 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! Joe Larsen ********************* Talent Acquisition Specialist Senior 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 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

The Managing Director of Corporate Finance is a key member of the finance leadership team, responsible for leading the company's financial strategy, capital management, and treasury operations. This executive provides strategic financial insight and leadership to support sustainable growth, profitability, and effective risk management across the enterprise. This role requires a seasoned finance leader with deep expertise in financial management, including capital optimization and performance analytics, as well as the ability to translate complex financial insights into actionable business strategies. Key Responsibilities * Partner with the CFO and executive leadership team to develop and execute the company's long-term financial strategy. * Provide strategic and financial guidance to support corporate objectives, including growth initiatives, profitability targets, and capital efficiency. * Lead capital management strategy, capital allocation decisions, and treasury operations to optimize liquidity and financial flexibility. Qualifications & Experience * Master's degree in Accounting, Finance, or a related field preferred. * Professional accounting or finance designation (e.g., CPA, CA, ACCA, CFA) preferred. * 10+ years of progressive financial leadership experience, including senior executive or director-level roles. * Demonstrated experience in strategic financial planning, governance, and executive-level decision support. Salary Range: The pay range for this position is $210,000 to $300,000 annually. Actual compensation will vary based on multiple factors, including employee knowledge and experience, role scope, business needs, geographical location, and internal equity. 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.

The Receptionist & Administrative Support Associate is a highly motivated individual committed to delivering exceptional service to both internal and external clients. The Associate will maintain a professional and welcoming environment, be responsive to diverse client needs, and proactively support the success of the Customer Contact Service department. This position will follow a Monday through Friday schedule. Monday from 10-6pm and Tuesday through Friday from 8-4pm. This role reports five days in the office in our Boston location. Essential Functions and Responsibilities * Deliver outstanding service by addressing client concerns, researching solutions, and taking ownership through to resolution. * Manage the operation of the switchboard and appropriately direct incoming calls. * Perform daily administrative tasks including document indexing, tracking and sorting subpoenas, coordinating department celebrations, and assisting with high-priority projects. * Train team members who will provide backup support for reception responsibilities. * Support customer inquiries by consistently identifying and executing "Yes" opportunities during each interaction. * Demonstrate schedule flexibility to provide coverage during unforeseen gaps, including support for executive staff during absences. Qualities & Education * Proficiency in Microsoft Office Suite (Word, Excel, PowerPoint, Outlook). * Ability to work both independently and collaboratively in a fast-paced environment. * Excellent interpersonal, communication, and analytical skills. * Strong research, organizational, and problem-solving abilities. * Bachelor's degree preferred. * Minimum of 2 years of professional work experience. 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: $41,500 - $55,500 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 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

This role would own voice and text analytics and insights. This would include sourcing, managing, structuring, and analyzing large amounts of structured and unstructured data from multiple sources including websites, apps, voice analytics, and third-party data vendors. Techniques include building automated data pipelines, web scraping, identifying trends and patterns in unstructured data, automated quality assurance and developing high-quality data visualizations and analytics solutions. Responsibilities: * Build complex data models that transform raw information into actionable business insights. * Web scraping, analysis, and automation of unstructured data flows. * Create intuitive dashboards and reports that simplify data comprehension across all organizational levels. * Troubleshoot and resolve data-related issues proactively. * Subject Matter expert in extracting data from VOC/CX systems such as Voice Analytics and Automated Quality Management and Datawarehouse to illustrate easily digestible trends and results of actions. * Implement enhancements to VA categories and Automated Quality Assurance Form Designer to uncover and promote insights. * Collaborate with teams to identify and bridge gaps in voice of the customer offerings. * Conduct thorough exploratory data analysis to ensure quality and consistency. * Maintain a state of constant communication and collaboration. * Root cause and driver analysis * Participate in a company-wide customer success motion through content, and data to and from stakeholder organizations. * Support the development a customer lifecycle model that ensures value realization and has a measurable impact on customer outcomes. Qualifications: * 5+ years of relevant experience. * AWS expertise Experience with tools like Lamda, Sagemaker and notebook jobs. * Expert-level proficiency in Power Bi or Tableau (data modeling, DAX, Power Query, Power BI Service). * Strong understanding of data warehousing concepts and integration techniques. * Experience managing large, complex datasets from multiple sources. * Bachelor's degree in computer science, statistics, Information Systems, or related field Salary Range: The pay range for this position is $94,000 to $132,000 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-SM1

Plymouth Rock Assurance is looking for a claims operations specialist who can conceptualize, design, test, and/or execute ideas resulting in new and viable business processes and offerings to build a sustainable competitive advantage. This role would be responsible for working in Project Management, Vendor Management as well as Training and Quality & Compliance. This is a high profile position with a significant impact on the organization. This role will be instrumental in the development of our quality and compliance team as well as other projects which will influence the homeowners organization. This person will be responsible for the facilitation, planning, execution, and delivery of moderately complex claims projects intended to accomplish business goals and objectives within prescribed timeframes and budgets. They will also be responsible for developing and implementing quality assurance/control programs to ensure effective and efficient policies, processes, and procedures are aligned and followed. Responsibilities: Vendor Management * Build influential partnerships across the homeowners claims industry to uncover competitive insights, synergies, and explore cutting edge solutions * Collaborates with key stakeholders, vendors and project/program teams to identify mutually beneficial outcomes for competing priorities and negotiate timelines to ensure objectives are met. * Lead industry-disrupting technology initiatives * Partner with business owners of key outsourced capabilities, leverage data to measure effectiveness and ensure work goes to the right vendors based on past performance. * Work with claims leaders to define opportunities where sourcing is the appropriate lever to bring expertise or scale to our operation to improve claims outcomes and member service. * Manage expense process, and maintain ongoing compliance, accountability, and measurement. Ensure vendor regulatory compliance and usage of claims best practices, while meeting targets for service, loss mitigation, productivity and expense management. Training & Onboarding * Lead efforts to implement and train the claims staff on new technology and vendor programs * Lead training team members in maintaining schedule to move organization forward with appropriate business initiatives * Collaborate with claims leaders to enhance the employee onboarding program and coordinate with business owners to facilitate development of programs as necessary Quality & Compliance * Lead efforts to ensure quality and compliance expectations are met throughout the operation * Plans, develops, executes and monitors all Quality evaluation processes and procedures as well as specialty evaluation requests, ad-hoc studies and projects. * Coordinate staff training to address deficiencies or opportunities surfaced through quality audits * Provides guidance and support related to various review and evaluation aspects, including but not, limited to assisting with action plans and follow-up on plan execution. Identifies opportunities to automate/streamline quality and compliance efforts. * Communicates on behalf of Plymouth Rock to regulatory and governmental inquiries and maintains a central file for such documents Qualifications: * Bachelor's Degree OR 3 years of related homeowners experience beyond the minimum required may be substituted in lieu of a degree. * Comprehensive understanding of 1st Party and/or 3rd Party Property Claims * Comprehensive knowledge and demonstrated application of project management tools and methodologies. * Collaboration skills in a matrixed environment including providing consultative guidance to help solve enterprise level issues. * Possess an understanding of scope definition, process and solution mapping; process structures and components; and standard project planning methodologies. * Experience supporting projects with complex deliverables * Understanding of State specific regulations and property and casualty homeowner claims process * Excellent written and verbal communication skills. * Strong organization and research skills. * Detail oriented and curious. * Personable and able to work effectively with a wide variety of people. Salary Range: The pay range for this position is $98,000 to $133,500 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-SK1

This temporary position will start in January 2026 and will end according to your availability, likely in the summer months. This position will be critical in advancing our mission to drive profit-focused technical excellence and innovation within the Plymouth Rock Group of Companies. The position will be responsible for research and development of new predictive models and new analytical techniques around insurance pure premiums, customer lifetime value, customer buying behaviors and other related topics utilizing internal and external data. This work will be used in setting pricing, underwriting and product strategies for the Plymouth Rock group of Companies. The analysis and modeling will be tested via implementation both broadly and on a pilot basis to allow us to learn and refine our approaches in rapid succession. Essential Functions and Responsibilities: Data Analysis: The Data Science Intern will work with internal and external data to understand key drivers of expected insurance losses and lifetime customer value. This will require that the Intern acquires an understanding of various internal and external data sources, is able to illicit hypothesis from internal personnel regarding key variables and test those hypotheses using available data. Modeling: The Data Science Intern will help develop and enhance models used in a variety of contexts within the product management structure of Plymouth Rock. The Intern will be responsible for advancing the modeling capabilities within Plymouth Rock and transferring those advancements to other product management personnel. Implementation: The Data Science Intern will work with the product community to facilitate the application of models developed considering the regulatory and competitive contexts within which we operate. This will include ensuring that models are well understood, the implications are appropriately assessed, implementation plans are defined, validation of results are undertaken, and adjustments are made rapidly. Qualifications: * Graduate Student from a program (doctoral preferred) in the areas of economics, statistics, or a related field (background in Bayesian statistics preferred). * Practical experience in Econometrics and Statistics, preferably in a business context. * Strong written and oral communication skills and an ability to communicate technical concepts to both technical and non-technical audiences. * High standards for the work products delivered. * Creative thinker with the ability to synthesize information from various sources and apply that information to concrete business problems. * Flexibility and resiliency characteristic of a professional. * Knowledge of, and experience with, the technical aspects of insurance is a plus. * Proficiency with modeling programming language (SQL, R, SAS, Python). The pay range for this position is $25 to $28 per hour. Actual compensation will vary based on multiple factors, including employee knowledge and experience, role scope, business needs, geographical location, and internal equity. Why work for us: * Friendly and collaborate work culture * Free On-site gym access * Free Coffee and Snacks * Company social events * Lunch and Learn Leadership program * Business Casual (Can wear jeans and sneakers!) * Convenient Location - across from South Station! 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".

As a Safety Services Consultant Senior, you will work with Corporate Risk Management, Safety Management, and Plant/Facility Management contacts as well as brokerage firms. Sentry's dedication to customer service is embodied by our best employees. At Sentry, our associates take care of our customers with a passion for service and delivering business results. We are currently seeking an experienced, self-motivated and results driven individual to fill an open position in our National Accounts Risk Control Division. As a Safety Services Consultant Senior, you will work with Corporate Risk Management, Safety Management, and Plant/Facility Management contacts as well as brokerage firms in Tennessee coordinating Safety and Industrial Hygiene Services for our causality line of business for our National Account customers (large deductible programs). What You'll Do The following are some of the responsibilities of the National Account Risk Control Consultant Senior that would reside in Tennessee (greater Nashville area) Design, develop and manage Service Plans for large, multi-location National Accounts and coordinate service activities (casualty services) with other National Account consultants/staff specialists. Plan and deliver Safety/Risk Management services to our National Account customers to include Safety Program Assessments/Gap Analysis, Leadership and Safety (Compliance) Training, Program Development, Loss Analysis & Benchmarking, Ergonomic and Machine Guarding Assessments, and assistance in Safety Culture Development. Develop, coordinate, and conduct safety training programs and seminars for insured and non-insured customers to educate management and elevate their understanding and awareness of safety, OSHA, loss potential and injury reduction techniques. Maintain proficient knowledge in all aspects of Safety Management Practices and demonstrate technical expertise in specialty area(s) such as Ergonomics, Machine Guarding, Behavior Based Safety, Accident Investigation Principles & Root Cause Analysis, Safety Culture Development, Metric Development, OSHA Compliance, Fleet Safety, and Product Liability. Provide supplemental Industrial Hygiene Services to include noise and air quality surveys (i.e. welding fumes, dust, organics, oil mist, IAQ, etc.) to support our Industrial Hygiene team and provide ongoing customer support on a National Account level. The National Account Risk Control Consultant Sr. enhances the client's technical knowledge and expertise through professional seminars and topic research as advances occur. What It Takes Four-year degree within Safety Sciences is preferred, or equivalent work experience 5+ years of advanced knowledge in safety/industrial hygiene with a National Property & Casualty Insurance Carrier preferred Extensive experience in coordinating and servicing large or multi-location National Accounts Knowledge of OSHA, ANSI, NFPA Standards Certified Safety Professional (CSP), or willingness to pursue is desired An acceptable motor vehicle record and ability to perform extensive travel is required (50% travel) 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! Talent Acquisition Specialist 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.

Plymouth Rock Assurance is looking for a talented and motivated Software Engineering Manager who will lead a team of highly technical full stack Java Developers to design, develop, support and implement industry leading eBusiness applications for home owners and umbrella insurance. This person will lead inception/iteration planning meetings, oversee feasibility research and lead collaboration and strategy alignment by working cross-functionally. In addition, this person will serve as the anchor of the team by mentoring Senior Engineers, providing technical leadership, resolving technical issues and promoting a spirit of collegiality and partnership across the firm. Essential Functions and Responsibilities: * Apply engineering standards and methodologies in order to analyze, design, develop, deploy and support software solutions to drive strong performance and high availability and exceed customer expectations. * Oversee source code and unit test case development. * Work with Business Analysts to understand requirements and translate to design. * Establish, aggregate, and share team standards and best practices across the department. * Coach and mentor employees to deliver continuous improvement and develop their professional skills and capabilities. * Functional/system integration testing support. * Plan and direct activities with the team and stakeholders to maximize technological productivity. * Architecture and design reviews. * Assess problems and solutions to contribute technical alternatives. * Impact analysis and component design. * Set clear expectations and create a positive work environment based on accountability, in collaboration with the engineering and management teams. * System/application architecture. * Develop guidelines and standards. * Support production as needed and meet development schedules. * Help the team scale effectively: identify, recruit, interview, and hire new engineers. Qualifications and Education: * Bachelor's or Master's degree (preferred) in Computer Science or related field. * 10+ years of professional experience and expert skills in JAVA/J2EE, Object oriented software design and development, Design Patterns, XML, and SQL. * Minimum 5 years of experience in Web application design and development. * Minimum 5 years development experience in Java/J2EE technologies. * Minimum 3 years of experience leading other Developers. * Self-motivated and directed, with the ability to effectively prioritize and execute tasks in a high-pressure environment. * A strong understanding of non-functional requirements (performance, scalability, maintainability, security). * Excellent design skills (class diagrams, sequence diagrams, activity diagrams, etc.) * Leadership and cross-communication skills to work with other domains/teams. * Desirable knowledge includes P&C Insurance industry, JBOSS, ESB (Mule), modern JavaScript libraries such as JQuery, AJAX, JUnit, Spring MVC, Angular, Web Services, Amazon Web Services, Kubernetes, Dev Ops and Jira. * Java Certifications (developer, web component, and architect) preferred. * Knowledge of IT concepts, strategies and methodologies. * Thorough understanding of layered systems architectures and layered solutions and designs. * Knowledge of diverse technologies and new technical architecture principles and concepts. * Highly proficient in software engineering languages and tools; ability to develop on multiple platforms. * Thorough knowledge of a business function(s) and IT industry business issues, extensive knowledge of business operations, strategies and objectives. * Strong communication, facilitation and consensus building skills. 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 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

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.