Director of Generative AI & Agentic Engineering

Plymouth Rock Assurance Corporation; Boston (MA); Hybrid; USD 205,000 - 282,000; Full time

Benefits offered by this job

Hybrid work environment

Boston location

Competitive compensation

401(k)

Paid time off

Job summary

Plymouth Rock Assurance Corporation is seeking a strategic and hands-on Director, AI Engineering to lead the design, development, and scaling of Generative and Agentic AI systems across the enterprise. You will build AI-powered customer experiences, internal tools, and scalable platforms driven by LLMs and RAG architectures.

The role requires deep AI stack expertise, strong leadership, and collaboration with technology, data, product, operations, and business teams to translate AI investments

Qualifications

• Bachelor’s or Master’s degree in Computer Science, Artificial Intelligence, Machine Learning, Applied Mathematics, or related field.
• 10+ years of software engineering/platform engineering/data science, with 2+ years in AI systems development.
• 5+ years of engineering leadership leading AI/ML teams.
• Experience delivering LLM-powered applications and AI/ML systems at enterprise scale.
• Strong knowledge of Python and AI/ML tools (NumPy, Pandas, SciPy, Scikit-learn).
• Experience with cloud AI infrastructure (AWS/Azure/GCP) and modern delivery practices.
• Experience with MLOps/LLMOps, observability, and continuous improvement for AI systems.

Responsibilities

• Define and lead AI engineering strategy, target architecture, and roadmap for Generative and Agentic AI across the enterprise.
• Manage and mentor a high-performing AI engineering team.
• Design, build, and oversee deployment of scalable LLM-powered applications and AI-native products.
• Lead development of AI agents, agentic platforms, and autonomous workflows.
• Implement RAG architectures to leverage proprietary data and enterprise systems.

Skills

Strategic leadership

AI engineering

Python

LLM ecosystems

RAG architectures

MLOps

Cloud infrastructure

Stakeholder communication

Product partnering

Education

Bachelor's or Master's in CS/AI/Mathematics

Tools

OpenAI/Anthropic/Google/LLMs

LangChain

Vector databases

APIs & MCP servers

MLOps/LLMOps tooling

Job description

Plymouth Rock Assurance Corporation is seeking a strategic and hands-on Director, AI Engineering to lead the design, development, and scaling of Generative and Agentic AI systems across the enterprise. You will build AI-powered customer experiences, internal tools, and scalable platforms driven by LLMs and RAG architectures.

The role requires deep AI stack expertise, strong leadership, and collaboration with technology, data, product, operations, and business teams to translate AI investments