Vice President Artificial Intelligence & Enterprise Architecture

Plymouth Rock Assurance • Boston, MA

7h • $350,000 - $450,000

About The Position

The Vice President Artificial Intelligence & Enterprise Architecture will be
responsible for defining, governing, and scaling the company’s artificial
intelligence strategy to drive underwriting excellence, claims efficiency,
operational productivity, and superior customer outcomes. As a member of the
executive leadership team, the Vice President will ensure that AI initiatives
are aligned with business strategy, regulatory expectations, ethical standards,
and risk management frameworks specific to the property & casualty insurance
industry.

This role will lead the transition from experimentation to enterprise-grade AI,
embedding advanced analytics, machine learning, and generative AI across core
insurance functions while ensuring transparency, fairness, security, and
compliance. The ideal candidate will combine deep expertise in artificial
intelligence with strong strategic vision, exceptional communicative and
persuasive skills, and an ability to lead transformative projects from inception
to execution. An advanced degree (Master’s or Ph.D.) in Computer Science,
Engineering, Data Science, or a related field, is required. Unusually high
levels of energy, motivation, and determination are also required.

Requirements

• An advanced degree (Master’s or Ph.D.) in Computer Science, Engineering, Data Science, or a related field, is required.
• Unusually high levels of energy, motivation, and determination are also required.

Responsibilities

• Define and execute a multi-year enterprise AI strategy aligned with corporate objectives, growth plans, and risk appetite.
• Serve as executive owner of AI vision, roadmap, investment prioritization, and value realization.
• Propose AI strategies that align with the company’s overall business objectives and identify opportunities where AI can drive innovation, efficiency, and business transformation.
• Collaborate with senior executives, department heads, and cross-functional teams to align AI initiatives with company goals.

What This Job Offers

• Job Type: Full-time
• Career Level: Executive
• Education Level: Ph.D. or professional degree