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.

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”.

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