VP AI Strategy & Transformation Leader

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

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).