Vice President & Chief Data Officer

Vice President & Chief Data Officer

The Vice President & Chief Data Officer (CDO) leads Plymouth Rock’s enterprise data strategy to drive innovation, operational excellence, and business growth. This includes overseeing the modernization of data platforms and tools. The CDO ensures that data is treated as a strategic asset—trusted, accessible, well‑governed, and responsibly leveraged to advance analytics, automation, and emerging AI capabilities.

Partnering closely with business and technology leaders, the CDO identifies critical data sources, enriches the organization’s data ecosystem, and enables the safe and effective use of AI across underwriting, claims, risk management, and customer experience. This role blends strategic vision with innovation leadership to accelerate Plymouth Rock’s transformation into a truly data‑driven enterprise.

• Strategic Leadership
  • Develop and execute an enterprise data strategy that aligns with the company’s business objectives and digital transformation goals.
  • Serve as the organization’s leading advocate for the strategic use of data to power analytics and AI initiatives. Drive programs to migrate existing datasets to the cloud, define standards for collecting new data, and ensure consistent formats and structures across the enterprise.
  • Champion a data‑first culture that prioritizes quality, transparency, and rapid innovation at all levels of the organization.
  • Partner with business unit leaders to ensure data initiatives deliver measurable, sustainable business outcomes.
• Enterprise Data Management
  • Oversee enterprise data architecture, integration, and modernization to ensure scalability, performance, and data interoperability.
  • Manage data platforms, lakes, and warehouses that serve as foundational assets for analytics and AI.
  • Catalog existing data and identify new and emerging data sources that can be used to gain a competitive advantage.
  • Steer the design and optimization of third‑party data ingestion pipelines to ensure seamless integration with internal systems.
  • Establish metadata management and cataloging systems to enable efficient discovery and use of data across the enterprise.
  • Drive the implementation of cloud data solutions that support both traditional analytics and AI workloads.
  • Promote enterprise‑wide stewardship and accountability for data quality and protection.
  • Establish and lead enterprise data governance frameworks to ensure data accuracy, completeness, lineage, and ethical use.
  • Maintain compliance with all applicable data privacy and regulatory standards (e.g., NYDFS).
• Data Sourcing & Enablement for AI
  • Identify, catalog, and curate internal and external data sources to support AI and advanced machine learning initiatives.
  • Drive partnerships with vendors, regulators, and industry groups to expand access to new, high‑quality, and compliant data sources for AI applications.
  • Collaborate with data engineering, architecture, and innovation teams to prepare structured and unstructured data for AI training and retrieval‑augmented generation (RAG) systems.

• Education
  • Bachelor’s degree in Data Science, Computer Science, Statistics, Actuarial Science, Business Administration, or a related field required.
  • Master’s degree (MS in Data Analytics, Artificial Intelligence, or Information Management) preferred.
• Experience Preferred
  • 10+ years of experience in data management, analytics, or related disciplines.
  • 5 years of successful senior leadership experience managing enterprise data or analytics functions.
  • Demonstrated experience and creativity identifying data sources.
  • Expertise in data quality management and data architecture best practices, including strong understanding of AI/GenAI data needs, including text, image, and structured data preparation.

The pay range for this position is $250,000 to $375,000 annually. Actual compensation will vary based on multiple factors, including employee knowledge and experience, role scope, business needs, geographical location, and internal equity.

The Plymouth Rock Company and its affiliated group of companies write and manage over $2.4 billion in personal and commercial auto and homeowner’s insurance throughout the Northeast and mid‑Atlantic, where we have built an unparalleled reputation for service. We continuously invest in technology, our employees thrive in our empowering environment, and our customers are among the most loyal in the industry.

The Plymouth Rock group of companies employs more than 1,900 people and is headquartered in Boston, Massachusetts. Plymouth Rock Assurance Corporation holds an A.M. Best rating of “A‑/Excellent”.