Director, Artificial Intelligence Engineering

Plymouth Rock Assurance•Boston, MA

6h•$205,000 - $282,000•Hybrid

About The Position

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.

Requirements

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

Nice To Haves

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

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

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