Director, Artificial Intelligence Engineering

We are seeking a hands-on Director, AI Engineering to lead the design, development, and scaling of Generative and Agentic AI systems across the enterprise. This role focuses on building LLM-powered applications, AI platforms, and reusable capabilities (e.g., RAG, MCP, multi-agent systems) to support both internal and customer-facing use cases. You’ll define strategy, lead a high-performing team, and translate AI investments into measurable business outcomes.

 

Key Responsibilities

• Define and execute AI engineering strategy, architecture, and roadmap 
• Lead and grow a high-performing AI engineering team 
• Build and deploy scalable LLM-powered applications and AI products 
• Develop agentic systems, autonomous workflows, and RAG pipelines 
• Establish standards for prompts, evaluation, security, testing, and production readiness 
• Implement MLOps/LLMOps pipelines and modern AI delivery practices (CI/CD, Agile) 
• Partner across tech, data, security, legal, and business teams to ensure compliant, high-impact solutions 
• Drive vendor selection, build-vs-buy decisions, and external partnerships 
• Identify high-value use cases and track success metrics (adoption, impact, cost, quality) 
• Stay current with emerging AI technologies and best practices 

 

Required Qualifications

• Bachelor’s or Master’s in CS, AI/ML, or a related field 
• 10+ years in software and/or AI/ML engineering with 5+ years in leadership roles 
• Experience delivering LLM-based AI systems at enterprise scale 
• Expert prompt engineering skills and experience with AI assisted software development
• Strong Python and modern AI/ML tooling (e.g., LLM and Agentic AI  frameworks, vector DBs, APIs)
• Experience with RAG, MCP, AI agent design and orchestration, MLOps/LLMOps, and cloud platforms (AWS/Azure/GCP)
• Knowledge of AI security, governance, and compliance 
• Strong leadership and cross-functional communication skills 

 

Preferred Qualifications

• Advanced degree (MS/PhD) 
• Experience with designing, building, and scaling agentic AI platforms, model fine-tuning, and multi-modal AI 
• Familiarity with agentic AI frameworks like LangChain, LangGraph, LlamaIndex, Crewai, Frontier, or similar 
• Background in regulated industries (e.g., insurance, finance) 
• Experience leading AI transformation and large-scale initiatives 

 

What We Offer

• Leadership role shaping enterprise AI strategy 
• High-impact work across customer and operational experiences 
• Collaborative, cross-functional environment 
• Competitive compensation and hybrid work in Boston

Salary Range:​

The pay range for this position is $205,000 to $282,000 annually. Actual compensation will vary based on multiple factors, including employee knowledge and experience, role scope, business needs, geographical location, and internal equity.​

 Perks and Benefits:

• 4 weeks accrued paid time off + 9 paid national holidays per year
• Free onsite gym at our Boston Location
• Tuition Reimbursement
• Low cost and excellent coverage health insurance options that start on Day 1 (medical, dental, vision)
• Robust health and wellness program and fitness reimbursements
• Auto and home insurance discounts
• Matching gift opportunities
• Annual 401(k) Employer Contribution (up to 7.5% of your base salary)
• Various Paid Family leave options including Paid Parental Leave
• Resources to promote Professional Development (LinkedIn Learning and licensure assistance)
• Convenient location directly across from South Station and Pre-Tax Commuter Benefits

About the Company

The Plymouth Rock Company and its affiliated group of companies write and manage over $2.3 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 co