Vice President Artificial Intelligence

About the role

The Vice President Artificial Intelligence will define, govern, and scale the company’s artificial intelligence strategy to drive underwriting excellence, claims efficiency, operational productivity, and superior customer outcomes. 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.

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

Requirements

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 preferred.

Qualifications

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.

Skills

The successful candidate will possess a combination of technical and leadership skills, including:

• Deep understanding of artificial intelligence principles and technologies.
• Strong strategic thinking and business acumen.
• Excellent communication and interpersonal skills.
• Experience leading complex, multi-disciplinary projects.
• Ability to build and manage high-performing teams.

Benefits

Plymouth Rock offers a comprehensive benefits package that includes:

• Health, dental, and vision insurance.
• Retirement savings plan with employer match.
• Flexible work arrangements.
• Professional development opportunities.

Pay

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.

Schedule

This is a full-time position based in Plymouth Rock's headquarters in Boston.