Vice President Artificial Intelligence

plymouthrock; Boston (MA); On-site; USD 400,000 - 600,000; Full time

Job summary

Plymouth Rock seeks a Vice President of Artificial Intelligence in Boston to define, govern, and scale AI across underwriting, claims, and operations. You’ll lead enterprise AI initiatives, ensuring alignment with strategy, ethics, risk, and regulatory standards while driving customer outcomes.

The role requires exceptional strategic vision, executive communication, and the ability to lead transformative projects from inception to execution, with an advanced degree preferred (MS/PhD).

Qualifications

• Advanced degree preferred in Computer Science, Engineering, Data Science, or related field.
• Experience leading large AI programs and transitioning from experiments to enterprise AI.
• Strong understanding of regulatory, ethics, and risk-management considerations in insurance AI.

Responsibilities

• Define and execute a multi-year enterprise AI strategy aligned with objectives and risk appetite.
• Own AI vision, roadmap, investments, and value realization at executive level.
• Identify opportunities where AI drives innovation and transformation.
• Collaborate with senior executives and cross-functional teams to align AI initiatives with goals.
• Build and develop a high-performing AI/ML team of ~25 professionals.

Skills

Executive leadership

AI strategy

Stakeholder comms

Cross-functional collab

Regulatory awareness

Risk management

Strategic thinking

Team building

Education

Master's or PhD in CS/Engineering/Data Science

Job description

The Vice President Artificial Intelligence 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 preferred. Unusually high levels of energy, motivation, and determination are also referred.

In this role, you will:

• 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.
• Build and develop a high-performing team of 25 AI/ML professionals to design, implement, and scale advanced AI and machine learning solutions.

Salary Range:

The base salary for this position ranges from $400,000 to $600,000 annually, with substantial additional compensation components that could potentially double the total compensation package.

About Plymouth Rock

Founded in 1982 and headquartered in Boston, writing approximately $2.5 billion in annual premiums, Plymouth Rock is a privately held insurer specializing in automobile and home insurance. Plymouth Rock considers itself to be the “largest of the entrepreneurial insurers” and the “smallest of the large insurers.” We blend the agility, innovation, and growth potential of a dynamic startup with the resources, stability, and security of a well-established organization.