Plymouth Rock Assurance

Provide tier 2/3 support for managing, maintaining, and securing organizational endpoints including laptops and mobile devices, including OS patching, software deployment, and onboarding/offboarding. | Bachelor's degree in Computer Science or IT, advanced knowledge of Microsoft 365, Active Directory, SCCM, Intune, strong troubleshooting skills, and familiarity with Windows and macOS. | Senior Desktop Support Analyst   The Senior Desktop Support Analyst supports the IT team by providing tier 2/3 support in managing, maintaining, and securing an organization's endpoints, such as laptops, desktops, and mobile devices. This includes device management, software deployments, and user support. The ideal candidate is technically inclined, eager to learn, and able to work collaboratively within a dynamic IT environment.  They should have a strong focus on customer service and operational excellence.   Office location and hours: This position is based in Boston Massachusetts, currently 4 days in the office and 1 remote workday. Hours are 8:00am – 4:00pm.  Availability for occasional travel and on-call support is essential.    Responsibilities: * Responsibilities include assisting with the deployment and maintenance of various devices, managing OS and application patching using tools like Intune and Jamf, monitoring endpoint security, and troubleshooting hardware and software issues. * Collaboration with IT teams on software deployment and maintenance, assist with patch management, maintain documentation, and provide user support and training on best practices.  * Assist with onboarding/offboarding processes, ensuring timely provisioning and deprovisioning of devices. Support video conferencing systems and remote access tools.   Qualifications: * Required skills include familiarity with Windows and macOS. Advanced knowledge of Microsoft 365 and Active directory group policy management as well as SCCM and Intune.  * Must have strong troubleshooting and problem-solving abilities, excellent communication, ability to work independently and in a team, and eagerness to learn new technologies.  * Basic understanding of networking and video conferencing technologies. * Preferred qualifications include experience with endpoint management tools such Jamf, and familiarity with scripting languages like PowerShell or Python, information technology service management and basic knowledge of networking and video conference support. * A Bachelor’s degree in Computer Science, IT, or a related field (or equivalent experience) is required. ITIL certification and experience in IT support or a similar endpoint support role is also beneficial.    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: $83,500 to $117,000 per 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

Support comparative rater optimization, competitive intelligence, and analytics to improve business performance. | Bachelor's degree with 3-7 years in insurance or business intelligence analytics, strong technical and analytical skills, and experience with comparative rating platforms. | The Senior Analyst, Comparative Rater Strategy & Competitive Intelligence is responsible for supporting Plymouth Rock's Partner distribution channel through comparative rater optimization, competitive intelligence, performance analytics, and business insights. This role serves as a key contributor in ensuring Plymouth Rock maintains a strong competitive position across comparative rating platforms while delivering actionable insights that improve quote performance, policy conversion, operational efficiency, and profitable growth. Working closely with Product Management, Underwriting, Marketing, IT, and vendor partners, the Senior Analyst will monitor comparative rater performance, support platform implementations, conduct competitive analyses, and develop reporting and recommendations that drive business performance. The ideal candidate combines strong analytical skills, technical aptitude, intellectual curiosity, and a passion for understanding how pricing, product design, and distribution strategy influence market competitiveness. RESPONSIBILITIES Comparative Rater Performance & Optimization • Monitor and analyze comparative rater performance across platforms including EZLynx, Vertafore, PL Rating, Bolt, EPIC, and other comparative rating vendors. • Track quote volume, quote return rates, ranking position, bridge rates, policy conversion, and carrier visibility metrics. • Analyze company-specific questions, soft and hard defaults, quote return performance, and carrier visibility strategies to improve competitiveness, quote volume, and policy conversion. • Support implementation, testing, and validation of product, rate, underwriting, and filing changes across comparative rating platforms. • Assist with comparative rater quality assurance, production monitoring, issue identification, and resolution activities. • Partner with IT, Product, and vendor partners to investigate data mapping issues, configuration concerns, and quoting discrepancies. • Support implementation of filtering strategies and quoting workflows designed to improve underwriting quality and loss ratio performance. • Participate in vendor testing cycles and platform releases to validate functionality prior to production deployment. • Maintain documentation related to comparative rater configurations, business rules, workflows, and vendor processes. Competitive Intelligence • Monitor competitor pricing positions, quoting performance, product offerings, and comparative rater visibility. • Develop recurring competitive intelligence reports, dashboards, and scorecards. • Analyze market competitiveness by state, product, agency segment, and distribution channel. • Identify emerging trends, opportunities, and competitive threats impacting the partner distribution channel. • Support development of executive reporting, business cases, and strategic recommendations. • Conduct ad hoc market research and competitor analysis projects. Analytics & Reporting • Develop and maintain dashboards, reports, and KPI tracking tools supporting comparative rater and Partner distribution channel performance. • Analyze quote-to-bind performance, conversion funnels, customer acquisition metrics, and channel effectiveness. • Support agency, partner, and comparative rater performance reporting. • Perform quantitative analyses supporting growth initiatives, business planning, and operational improvements. • Ensure data accuracy, reporting consistency, and analytical integrity across assigned reporting processes. • Support ROI analysis and business case development for new initiatives, vendor opportunities, and growth investments. Cross-Functional Partnership • Collaborate with Product, Underwriting, Marketing, Distribution, Finance, and IT teams to support strategic initiatives. • Translate analytical findings into actionable business recommendations. • Present insights, performance results, and recommendations to business stakeholders. • Serve as a subject matter resource on comparative rater operations, performance metrics, and competitive positioning. QUALIFICATIONS • Bachelor's degree in Mathematics, Statistics, Economics, Business Analytics, Finance, Computer Science, Actuarial Science, or related field. • 3–7 years of experience in insurance analytics, product analytics, business intelligence, competitive intelligence, comparative raters, or related disciplines. • Strong understanding of personal lines insurance products, pricing concepts, and distribution channels. • Experience with comparative rating platforms such as EZLynx, Vertafore, PL Rating, Bolt, EPIC, or similar solutions preferred. • Advanced Excel skills and experience working with large data sets. • SQL proficiency required. • Experience with Tableau, Power BI, SAS, Python, R, or similar analytical tools preferred. • Strong analytical, problem-solving, and critical-thinking skills. • Excellent written and verbal communication skills. • Ability to manage multiple priorities and thrive in a fast-paced environment. Key Success Metrics • Comparative rater quote return performance • Ranking position improvement • Quote-to-bind conversion improvement • Competitive intelligence reporting quality • Comparative rater implementation accuracy • Issue resolution effectiveness • Dashboard and reporting accuracy • Timeliness of analysis and recommendations • Stakeholder satisfaction • Adoption of analytical insights SALARY RANGE The pay range for this position is $88,000 to $137,000 annually. Actual compensation will vary based on multiple factors, including employee knowledge and experience, role scope, business needs, geographical location, and internal equity. PERKS & BENEFITS • 4 weeks accrued paid time off, 8 paid national holidays per year, and 2 floating holidays • Low cost and excellent coverage health insurance options that start on Day 1 (medical, dental, vision) • Annual 401(k) Employer Contribution • Free onsite gym and health center at our Woodbridge Location • Resources to promote Professional Development (LinkedIn Learning and licensure assistance) • Robust health and wellness program and fitness reimbursements • Various Paid Family leave options including Paid Parental Leave • Tuition Reimbursement 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