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Get Access To All JobsWe are seeking a strategic and hands-on Director, AI Engineering to lead the design, development, and scaling of Generative and Agentic AI systems that transform how our company operates and serves customers. This role focuses on building AI applications and reusable AI platform capabilities powered by large language models (LLMs), retrieval-augmented generation (RAG), Model Context Protocol (MCP), multi-agent systems, Agentic AI platforms, and modern AI/ML infrastructure across the enterprise for both internal and customer-facing use cases.
The ideal candidate combines deep expertise in a modern AI/ML stack with strong AI software engineering fundamentals, strong people leadership, and the ability to partner effectively across technology, data, product, operations, and business teams.
You will help define the AI engineering strategy and roadmap, lead a high-performing AI Engineering team, build and manage scalable AI products, establish standards for scalable and secure AI delivery, and help translate AI investments into measurable business outcomes.
Key Responsibilities
- Help to define and lead the execution of AI engineering strategy, target architecture, and roadmap for Generative and Agentic AI across the enterprise.
- Manage and motivate a high-performing team of AI engineers including coaching, mentoring, and scaling as required.
- Design, build, and oversee deployment of scalable LLM-powered applications and AI-native products for customer support, business operations, and internal productivity.
- Lead the development of AI agents, agentic platforms, and autonomous workflows capable of reasoning, planning, and executing multi-step tasks.
- Implement RAG architectures and pipelines to leverage proprietary data, internal knowledge bases, enterprise systems, and structured/unstructured content.
- Stand-up and evolve MCP servers, tool integrations, and multi-connectivity AI platforms to support secure orchestration across internal and external systems.
- Establish and oversee standards for prompt design, model evaluation, guardrails, observability, testing, and production readiness to ensure accuracy, resiliency, security, and regulatory compliance.
- Lead the design of MLOps and LLMOps pipelines for model lifecycle management, monitoring, continuous evaluation, and improvement.
- Leverage CI/CD and Agile methodologies for AI product development.
- Partner with architecture, security, legal, compliance, and data teams to ensure AI solutions meet requirements for privacy, governance, auditability, and responsible AI.
- Drive build vs. buy decisions, vendor selection, and collaboration with external partners, consultants, and internal teams to deliver scalable, high-quality AI solutions.
- Work closely with business leaders to identify and prioritize high-value use cases across the insurance business, process optimization, software development, and employee productivity.
- Define and track success metrics for adoption, quality, reliability, business impact, cost efficiency, and delivery velocity.
- Stay current with emerging advancements in AI/ML, Generative AI, agentic frameworks, model architectures, and enterprise AI engineering practices.
Required Qualifications
- Bachelor's or Master's degree in Computer Science, Artificial Intelligence, Machine Learning, Applied Mathematics, or a related field. Graduate degrees are preferred, but not necessary.
- 10+ years of experience in software engineering, platform engineering, machine learning, or data science, with 2+ years in AI systems development.
- 5+ years of engineering leadership experience, including leading, mentoring, and scaling high-performing technical or AI/ML teams.
- Proven experience delivering LLM-powered applications and AI/ML systems into production at enterprise scale.
- Deep understanding of AI supporting infrastructure, security, testing, and monitoring/maintenance pipelines.
- Strong knowledge of Python, with hands-on experience with AI/ML-relevant packages and tools, such as NumPy, Pandas, SciPy, and Scikit-learn.
- Deep experience with modern LLM ecosystems and tools, such as:
- OpenAI / Anthropic / Google / open-source LLMs / other
- Claude Code, Codex, Cursor, GitHub Copilot, or similar
- LangChain, LlamaIndex, Crewai, or similar orchestration frameworks
- Experience building RAG pipelines, working with vector databases, and integrating AI with enterprise data and application environments.
- Experience designing and integrating APIs, MCP servers, scalable backend services, and AI platform components.
- Strong understanding of prompt engineering, embeddings, model evaluation, fine-tuning, and agent design and orchestration.
- Experience with cloud-based AI infrastructure and modern software delivery practices across AWS, Azure, or GCP. Familiarity with SnowFlake is preferred.
- Experience with MLOps / LLMOps, evaluation frameworks, observability, and continuous improvement for AI systems in production.
- Strong understanding of AI governance, security, privacy, risk controls, and compliance in enterprise or regulated environments.
- Experience influencing cross-functional stakeholders and communicating effectively with senior technology and business leaders.
- Ability to balance hands-on technical depth with strategic leadership, organizational development, and execution discipline.
Preferred Qualifications
- Advanced degree (M.Sc. or Ph.D.) in a relevant field.
- Experience building AI agents, agentic platforms, or autonomous workflows in production.
- Experience leading senior engineers, or technical leads in a scaled engineering organization.
- Familiarity with agentic frameworks such as LangChain, LangGraph, AutoGen, CrewAI, OpenAI Agents SDK, Semantic Kernel, LlamaIndex, Frontier, or similar.
- Experience with fine-tuning LLMs or parameter-efficient fine-tuning (PEFT) methods such as LoRA, or similar.
- Experience with multi-modal AI, document processing, semantic search, knowledge assistants, and enterprise workflow automation.
- Familiarity with Java, JavaScript, and enterprise application environments.
- Experience with vendor management, budgeting, and buy-vs-build evaluation for AI platforms and tooling.
- Experience implementing responsible AI, governance frameworks, security, observability, and guardrails at scale.
- Experience leading AI transformation initiatives across large, matrixed organizations.
- Experience in the insurance industry, finance, or other regulated industries, with exposure to fraud detection, risk analysis, claims, underwriting, servicing customers, or document intelligence.
What We Offer
- Opportunity to shape the future of AI engineering in the insurance industry
- Leadership role building next-generation Generative and Agentic AI capabilities
- High-impact work across customer, employee, and operational experiences
- Collaborative environment with technology, data, and business leaders
- Competitive compensation and benefits
- Hybrid work environment in Boston
- Opportunity to build both enterprise AI platforms and high-value AI products that drive measurable business results
Impact
In this key role, you will shape how AI is engineered, governed, and scaled across the enterprise. You will help build an AI-first insurance company, leveraging Generative and Agentic AI to improve decision-making, streamline operations, accelerate service, and deliver better experiences for customers, business stakeholders.
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 continuously invest in technology, our employees thrive in our empowering environment, and our customers are among the most loyal in the industry. The Plymouth Rock group of companies employs more than 1,900 people and is headquartered in Boston, Massachusetts. Plymouth Rock Assurance Corporation holds an A.M. Best rating of “A-/Excellent”
We are seeking a strategic and hands-on Director, AI Engineering to lead the design, development, and scaling of Generative and Agentic AI systems that transform how our company operates and serves customers. This role focuses on building AI applications and reusable AI platform capabilities powered by large language models (LLMs), retrieval-augmented generation (RAG), Model Context Protocol (MCP), multi-agent systems, Agentic AI platforms, and modern AI/ML infrastructure across the enterprise for both internal and customer-facing use cases.
The ideal candidate combines deep expertise in a modern AI/ML stack with strong AI software engineering fundamentals, strong people leadership, and the ability to partner effectively across technology, data, product, operations, and business teams.
You will help define the AI engineering strategy and roadmap, lead a high-performing AI Engineering team, build and manage scalable AI products, establish standards for scalable and secure AI delivery, and help translate AI investments into measurable business outcomes.
Key Responsibilities
- Help to define and lead the execution of AI engineering strategy, target architecture, and roadmap for Generative and Agentic AI across the enterprise.
- Manage and motivate a high-performing team of AI engineers including coaching, mentoring, and scaling as required.
- Design, build, and oversee deployment of scalable LLM-powered applications and AI-native products for customer support, business operations, and internal productivity.
- Lead the development of AI agents, agentic platforms, and autonomous workflows capable of reasoning, planning, and executing multi-step tasks.
- Implement RAG architectures and pipelines to leverage proprietary data, internal knowledge bases, enterprise systems, and structured/unstructured content.
- Stand-up and evolve MCP servers, tool integrations, and multi-connectivity AI platforms to support secure orchestration across internal and external systems.
- Establish and oversee standards for prompt design, model evaluation, guardrails, observability, testing, and production readiness to ensure accuracy, resiliency, security, and regulatory compliance.
- Lead the design of MLOps and LLMOps pipelines for model lifecycle management, monitoring, continuous evaluation, and improvement.
- Leverage CI/CD and Agile methodologies for AI product development.
- Partner with architecture, security, legal, compliance, and data teams to ensure AI solutions meet requirements for privacy, governance, auditability, and responsible AI.
- Drive build vs. buy decisions, vendor selection, and collaboration with external partners, consultants, and internal teams to deliver scalable, high-quality AI solutions.
- Work closely with business leaders to identify and prioritize high-value use cases across the insurance business, process optimization, software development, and employee productivity.
- Define and track success metrics for adoption, quality, reliability, business impact, cost efficiency, and delivery velocity.
- Stay current with emerging advancements in AI/ML, Generative AI, agentic frameworks, model architectures, and enterprise AI engineering practices.
Required Qualifications
- Bachelor's or Master's degree in Computer Science, Artificial Intelligence, Machine Learning, Applied Mathematics, or a related field. Graduate degrees are preferred, but not necessary.
- 10+ years of experience in software engineering, platform engineering, machine learning, or data science, with 2+ years in AI systems development.
- 5+ years of engineering leadership experience, including leading, mentoring, and scaling high-performing technical or AI/ML teams.
- Proven experience delivering LLM-powered applications and AI/ML systems into production at enterprise scale.
- Deep understanding of AI supporting infrastructure, security, testing, and monitoring/maintenance pipelines.
- Strong knowledge of Python, with hands-on experience with AI/ML-relevant packages and tools, such as NumPy, Pandas, SciPy, and Scikit-learn.
- Deep experience with modern LLM ecosystems and tools, such as:
- OpenAI / Anthropic / Google / open-source LLMs / other
- Claude Code, Codex, Cursor, GitHub Copilot, or similar
- LangChain, LlamaIndex, Crewai, or similar orchestration frameworks
- Experience building RAG pipelines, working with vector databases, and integrating AI with enterprise data and application environments.
- Experience designing and integrating APIs, MCP servers, scalable backend services, and AI platform components.
- Strong understanding of prompt engineering, embeddings, model evaluation, fine-tuning, and agent design and orchestration.
- Experience with cloud-based AI infrastructure and modern software delivery practices across AWS, Azure, or GCP. Familiarity with SnowFlake is preferred.
- Experience with MLOps / LLMOps, evaluation frameworks, observability, and continuous improvement for AI systems in production.
- Strong understanding of AI governance, security, privacy, risk controls, and compliance in enterprise or regulated environments.
- Experience influencing cross-functional stakeholders and communicating effectively with senior technology and business leaders.
- Ability to balance hands-on technical depth with strategic leadership, organizational development, and execution discipline.
Preferred Qualifications
- Advanced degree (M.Sc. or Ph.D.) in a relevant field.
- Experience building AI agents, agentic platforms, or autonomous workflows in production.
- Experience leading senior engineers, or technical leads in a scaled engineering organization.
- Familiarity with agentic frameworks such as LangChain, LangGraph, AutoGen, CrewAI, OpenAI Agents SDK, Semantic Kernel, LlamaIndex, Frontier, or similar.
- Experience with fine-tuning LLMs or parameter-efficient fine-tuning (PEFT) methods such as LoRA, or similar.
- Experience with multi-modal AI, document processing, semantic search, knowledge assistants, and enterprise workflow automation.
- Familiarity with Java, JavaScript, and enterprise application environments.
- Experience with vendor management, budgeting, and buy-vs-build evaluation for AI platforms and tooling.
- Experience implementing responsible AI, governance frameworks, security, observability, and guardrails at scale.
- Experience leading AI transformation initiatives across large, matrixed organizations.
- Experience in the insurance industry, finance, or other regulated industries, with exposure to fraud detection, risk analysis, claims, underwriting, servicing customers, or document intelligence.
What We Offer
- Opportunity to shape the future of AI engineering in the insurance industry
- Leadership role building next-generation Generative and Agentic AI capabilities
- High-impact work across customer, employee, and operational experiences
- Collaborative environment with technology, data, and business leaders
- Competitive compensation and benefits
- Hybrid work environment in Boston
- Opportunity to build both enterprise AI platforms and high-value AI products that drive measurable business results
Impact
In this key role, you will shape how AI is engineered, governed, and scaled across the enterprise. You will help build an AI-first insurance company, leveraging Generative and Agentic AI to improve decision-making, streamline operations, accelerate service, and deliver better experiences for customers, business stakeholders.
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 continuously invest in technology, our employees thrive in our empowering environment, and our customers are among the most loyal in the industry. The Plymouth Rock group of companies employs more than 1,900 people and is headquartered in Boston, Massachusetts. Plymouth Rock Assurance Corporation holds an A.M. Best rating of “A-/Excellent”
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Get Access To All JobsTips for Finding Green Card Sponsorship as an AI Intern
Align your degree to SOC codes
PERM filings tie the role to a Standard Occupational Classification code. For AI Intern positions, codes like 15-2051 (Data Scientists) or 15-1299 require a degree in a specific field, so your transcript and credential evaluations need to match the employer's PERM job description precisely.
Target companies with intern-to-full-time pipelines
Employers only sponsor green cards for permanent, full-time positions. Focus on companies that convert interns to full-time roles, then initiate PERM after you convert, since no employer will sponsor a temporary intern position directly.
Search PERM filings before applying
Use Migrate Mate to filter employers by their green card filing history. Hiring managers at companies with active EB-2 or EB-3 PERM filings already understand the process, reducing the friction of introducing sponsorship in your offer negotiation.
Request an EB-3 professional track early
If your degree is a U.S. bachelor's or foreign equivalent in a relevant STEM field, you may qualify for EB-3 professional classification at the post-conversion full-time stage. Clarify this with your employer's HR team before accepting an offer, not after.
Confirm the employer's E-Verify enrollment
USCIS requires employers to be enrolled in E-Verify to sponsor certain employment-based green card petitions. Ask recruiters directly before your final interview round, as small AI startups frequently skip E-Verify enrollment until it becomes a compliance requirement.
Understand PERM advertising timelines
DOL requires employers to complete a mandatory recruitment period before filing a PERM application, which typically runs 30 to 180 days depending on the employer's specific ad placements. Budget for this lag when planning your timeline from offer acceptance to I-140 filing.
Green Card AI Intern: Frequently Asked Questions
Can an employer sponsor a green card for an AI Intern position directly?
No. PERM labor certification requires the sponsored position to be a permanent, full-time role. Internships are temporary by definition, so direct sponsorship of an AI Intern title isn't possible. The common path is to complete the internship, convert to a full-time AI or data science role, and then have the employer initiate PERM for that permanent position.
How does EB-3 green card sponsorship differ from H-1B for AI roles?
H-1B visa is a temporary status subject to an annual lottery with a cap of 85,000 slots. EB-3 leads to permanent residency with no annual cap at the petition level for most nationalities. The trade-off is time: EB-3 involves PERM labor certification, I-140 approval, and priority date waiting periods that can stretch multi-year, whereas H-1B status can begin within months of selection.
Does a foreign computer science degree qualify for EB-2 or EB-3 sponsorship in AI roles?
A foreign bachelor's degree in computer science, data science, or a closely related STEM field generally qualifies for EB-3 professional classification after credential evaluation confirms U.S. equivalency. EB-2 requires an advanced degree or its equivalent, so a master's or Ph.D. strengthens eligibility. Check the O*NET occupation profile for the specific SOC code your employer uses in the PERM filing to confirm degree field alignment.
How do I find AI employers who sponsor green cards?
Most job postings don't advertise PERM sponsorship explicitly. Migrate Mate lets you search AI and data science roles filtered by employers with verified green card filing histories, so you can target companies that have already gone through the PERM process rather than guessing which employers will sponsor after you receive an offer.
What is the prevailing wage requirement for AI Intern roles transitioning to full-time sponsored positions?
DOL requires employers to pay the prevailing wage for the specific role and work location as determined through the OFLC Wage Search tool. For AI and data science roles, prevailing wages are benchmarked against SOC-code data from the Bureau of Labor Statistics. Your employer must certify this wage on the PERM application, and the sponsored salary must meet or exceed that threshold at the time of filing.