Plymouth Rock Assurance is hiring: Senior Digital Data Analyst in Boston

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Overview

The Senior Digital Data Analyst will provide data analysis support to the Digital Strategy team by means of data-mining, research, analysis, building reports and data visualizations (automated and ad hoc), documentation and training for enhancements related to all Digital touchpoints and the associated business metrics. We are looking for an analytic thinker who is passionate about online and customer behavior analysis. In this role you will need to be dynamic multitasker with a focus on analytics that supports KPI’s and goal achievements. The ideal candidate is an analytical problem-solver who is deeply comfortable working in SQL, Python, can move seamlessly between exploratory analysis and production reporting, and is passionate about using data to improve digital experiences, operational efficiency, and business outcomes—particularly within an insurance or financial services environment.

Responsibilities

• Analyze customer behavior across web, mobile, and agent platforms to identify trends, drop-offs, friction points, and self-service opportunities
• Leverage digital analytics and behavioral tools (e.g., GA4, Heap, Tealium, FullStory, VWO, or similar) to:
• Track user journeys, funnels, and feature adoption
• Measure digital performance and customer engagement
• Support experimentation and A/B testing analysis
• Partner with Product and UX teams to define success metrics and ensure analytics instrumentation is accurate and scalable

Data Integration & Enablement

• Write advanced SQL queries to extract, join, and transform data from multiple sources (digital platforms, data warehouse, operational systems)
• Collaborate with data engineering and platform teams to ensure data quality, governance, and performance
• Integrate structured and semi-structured data sources to create meaningful, analysis-ready datasets

Visualization, Reporting & Storytelling

• Design and maintain Tableau dashboards and visualizations that provide clear, actionable insights for business and executive audiences
• Translate complex analyses into compelling narratives, recommendations, and decision-ready insights
• Build automated and ad hoc reporting to support KPIs, scorecards, and performance measurement

Advanced Analytics & Python Development

• Use Python as a primary analysis tool to:
• Perform exploratory data analysis, statistical modeling, and segmentation
• Build reusable analysis frameworks, scripts, and data pipelines
• Automate reporting, data validation, and insight generation
• Apply statistical and analytical techniques to uncover drivers of customer behavior, satisfaction, and operational outcomes
• Support or develop AI-enabled analytics use cases, such as:
• Predictive indicators of customer intent or call likelihood
• Behavioral scoring or intelligent segmentation
• AI-assisted summaries or insight generation

Process Improvement & Business Impact

• Identify inefficiencies and opportunities for improvement in digital and operational workflows (e.g., claims, policy servicing, billing, communications)
• Quantify business impact and support prioritization of digital and process improvement initiatives
• Partner cross-functionally with Digital Strategy, Product, Marketing, Claims, IT, and CX teams to support roadmaps and post-launch measurement

Required Qualifications and Education

• Bachelor’s degree in Analytics, Statistics, Mathematics, Data Science, Economics, Engineering, or a related field (Master’s preferred)
• 5+ years of experience in analytics, digital analytics, or process improvement roles
• Strong hands-on experience with digital analytics platforms such as: Heap, Tealium, GA4, FullStory, VWO (or equivalent tools)

• Advanced proficiency in:
• SQL for querying and transforming large datasets
• Tableau (or comparable visualization tools) for executive-level reporting
• Python
• Solid foundation in statistics, data analysis, and analytical problem-solving
• Experience working in or supporting insurance or financial services, with exposure to claims, policy servicing, billing, or customer experience workflows

Preferred / Nice To Have

• Experience in insurance or financial services (claims, policy servicing, billing, customer experience)
• Familiarity with AI/ML concepts or applied analytics use cases
• Experience with A/B testing and experimentation analysis
• Exposure to NoSQL databases (e.g., MongoDB, DocumentDB)
• Experience working in agile product or digital environments
• Knowledge of Lean, Six Sigma, or formal process improvement methodologies

Key Competencies

• Analytical rigor with a strong business and customer lens
• Ability to synthesize complex data into clear, actionable insights
• Comfort operating in ambiguous, evolving environments
• Strong communication skills with both technical and non-technical stakeholders
• High ownership, curiosity, and bias toward continuous improvement

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

Salary Range: $90,000-$120,000 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 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”.