VP, AI - First IT and Transformation

Department: Information Technology Location: Boston, MA (Remote / Hybrid eligible) Employment Type: Full-time Compensation: $230,000 – $270,000 annual base salary, depending on experience, qualifications, and geographic location

As the Vice President, AI-First IT and Transformation, you will play a key role in supporting The Mutual Group (TMG), GuideOne Insurance, and future members by establishing and scaling TMG's enterprise AI capability — helping the organization apply AI in practical, secure, and measurable ways across business processes, technology platforms, IT delivery, operations, and employee productivity.

This leader is accountable for moving AI beyond isolated tools and experiments into a governed, reusable, and scalable enterprise capability. The role partners with business leaders to identify and deliver AI-enabled improvements across underwriting, claims, operations, finance, customer experience, and employee productivity. It also guides the creation of AI-First platforms, establishes AI-first engineering practices, and enables responsible use of enterprise AI tools such as ChatGPT, Microsoft Copilot, and related productivity platforms.

The VP will build and lead a small, high-performing AI-First IT team that starts by creating new tools, platforms, patterns, and playbooks — serving as a catalyst, not a silo — helping TMG develop future-ready technology capabilities while maintaining strong security, privacy, governance, and operational discipline.

Key Accountabilities

Enterprise AI Strategy & Transformation Leadership

• Define and lead TMG's enterprise AI strategy in partnership with the CITO, business executives, technology leaders, and risk governance partners
• Establish the AI-First IT operating model, roadmap, governance approach, funding priorities, delivery rhythm, and measurable outcomes
• Build a disciplined portfolio of AI initiatives balancing experimentation, speed, security, business value, and risk management
• Serve as a thought leader and practical operator helping the organization understand where AI creates value, where it creates risk, and how to adopt it responsibly

AI Platforms, Architecture & Engineering Enablement

• Lead strategy and delivery of foundational AI platform capabilities supporting secure, scalable, and reusable AI-enabled applications
• Define architecture patterns for AI-First applications, copilots, intelligent workflows, automation agents, and enterprise knowledge solutions
• Guide platform capabilities including model access, retrieval frameworks, vector databases, prompt/response controls, observability, and governance guardrails
• Introduce AI-assisted software engineering practices across the SDLC — coding, testing, documentation, requirements analysis, code review, and workflow automation

Business Capability Enablement & Adoption

• Partner with underwriting, claims, operations, finance, and customer service to identify and deliver high-value AI-enabled process improvements
• Lead development of AI capabilities such as decision support, workflow automation, document intelligence, knowledge assistance, summarization, triage, and productivity tools
• Lead enterprise enablement of AI productivity tools including ChatGPT, Microsoft Copilot, and related assistants — including standards, training, adoption practices, and usage guardrails
• Build reusable playbooks, enablement models, and communities of practice that raise AI fluency across IT and the broader organization

Responsible AI, Governance & Risk Partnership

• Work closely with the Senior Director, AI & Technology Risk Governance to ensure AI adoption is responsible, secure, compliant, and aligned with TMG's risk appetite
• Embed security, privacy, responsible AI, sensitive data handling, human oversight, vendor risk, and production readiness into all AI platforms and use cases
• Create governance models that support responsible experimentation while protecting customers, employees, business partners, and enterprise data

Team Leadership, Delivery & Enterprise Collaboration

• Build and lead a small, high-performing AI-First IT organization with strong architecture, engineering, automation, platform, and delivery capabilities
• Lead from the front with a hands-on, roll-up-the-sleeves leadership style and strong ownership of outcomes
• Own delivery across scope, schedule, budget, quality, risk, dependencies, adoption, and business value
• Develop talent and create a culture of curiosity, accountability, disciplined experimentation, continuous learning, and measurable outcomes

Qualifications

• 15+ years of progressive technology leadership experience, including senior responsibility for engineering, architecture, platforms, data, infrastructure, automation, AI, or enterprise technology delivery
• Significant hands-on leadership experience with AI, machine learning, Generative AI, automation, advanced analytics, intelligent platforms, or developer productivity tools
• Strong understanding of Generative AI concepts and implementation patterns, including LLMs, SLMs, embeddings, prompt engineering, retrieval-augmented generation (RAG), vector databases, semantic search, and enterprise knowledge integration
• Experience with Agentic AI patterns, including autonomous/semi-autonomous agents, tool/function calling, workflow orchestration, human-in-the-loop controls, guardrails, monitoring, and safe deployment
• Familiarity with Model Context Protocol (MCP) or similar approaches for connecting AI systems to enterprise tools, data sources, APIs, and workflow actions in a secure and governed manner
• Understanding of AI/ML model lifecycle practices, including model selection, experimentation, validation, performance monitoring, drift detection, feedback loops, auditability, and responsible production deployment
• Proven experience leading **