VP, AI – First IT and Transformation

Key Responsibilities

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 that balances experimentation, speed, security, business value, operational readiness, and risk management.
• Translate emerging AI capabilities into practical, secure, scalable solutions that improve business outcomes, employee productivity, and technology delivery.
• Serve as a thought leader and practical operator who helps the organization understand where AI can create value, where it creates risk, and how to adopt it responsibly.

AI Platforms, Architecture & Engineering Enablement

• Lead the strategy and delivery of foundational AI platform capabilities that support secure, scalable, and reusable AI-enabled applications.
• Define architecture patterns for AI-First applications, copilots, intelligent workflows, automation agents, enterprise knowledge solutions, and reusable AI components.
• Guide platform capabilities such as model access, retrieval frameworks, vector databases, enterprise knowledge integration, prompt and response controls, observability, and governance guardrails.
• Introduce AI-assisted software engineering practices across the SDLC, including coding, testing, documentation, requirements analysis, code review, and engineering workflow automation.
• Partner with Applications, Engineering, Infrastructure, Operations, Architecture, Security, and Data teams to pilot, refine, and scale AI-enabled practices over time.

Business Capability Enablement & Adoption

• Partner with underwriting, claims, operations, finance, customer service, and other business functions to identify and deliver high-value AI-enabled process improvements.
• Lead the development of AI capabilities such as decision support, workflow automation, document intelligence, knowledge assistance, summarization, triage, productivity tools, and service quality improvements.
• Help business teams move from AI ideas to practical use cases with clear outcomes, adoption plans, controls, and value measures.
• Lead enterprise enablement of AI productivity tools such as 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 AI platforms, business use cases, engineering practices, operations, and employee tools.
• Partner with Security, Legal, Risk, Compliance, Data, Architecture, and business teams to define and operationalize enterprise AI governance.
• 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.
• Manage internal teams, contractors, vendors, and system integration partners to accelerate delivery while maintaining accountability and quality.
• Develop talent and create a culture of curiosity, accountability, disciplined experimentation, continuous learning, and measurable outcomes.

Qualification & Requirements

• 15+ years of progressive technology leadership experience, including senior responsibility for engineering, architecture, platforms, data, infrastructure, automation, AI, digital transformation, or enterprise technology delivery.
• Significant hands-on leadership experience with AI, machine learning, Generative AI, automation, advanced analytics, intelligent platforms, developer productivity tools, or emerging technology capabilities.
• Strong understanding of Generative AI concepts and implementation patterns, including LLMs, SLMs, embeddings, prompt engineering, retrieval-augmented generation, vector databases, semantic search, evaluation frameworks, and enterprise knowledge integration.
• Experience with Agentic AI patterns, including autonomous or semi-autonomous agents, tool/function calling, workflow orchestration, human-in-the-loop controls, guardrails, monitoring, and safe deployment practices.
• 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 controls, performance monitoring, drift detection, feedback loops, auditability, and responsible production deployment.
• Familiarity with enterprise AI platform capabilities such as model access gateways, model catalogs, AI orchestration layers, policy enforcement, prompt and response controls, observability, cost monitoring, and usage governance.
• Proven experience leading enterprise-scale technology transformation in a regulated environment, preferably insurance, financial services, or another highly governed industry.
• Strong technical fluency across cloud platforms, APIs, microservices, data platforms, observability, automation, cybersecurity, identity, privacy, and modern engineering practices.
• Experience enabling enterprise adoption of AI productivity tools such as ChatGPT, Microsoft Copilot, or similar platforms.
• Proven ability to lead internal teams, contractors, vendors, and system integration partners in a fast-paced, high-accountability environment.
• Strong financial and delivery discipline, including roadmap planning, cost management, vendor oversight, delivery governance, and value realization.
• Experience in P&C insurance, mutual insurance, shared services, multi-client service models, or technology environments supporting multiple business entities preferred.
• Bachelor’s degree in Computer Science, Engineering, Information Systems, Data Science, or related field required. Master’s degree or MBA preferred.

Leadership Attributes

• Inspirational thought leader with passion for building and scaling AI-enabled technology and business capabilities.
• Pragmatic, hands-on leader with strong bias for action and measurable outcomes.
• Strategic yet technical, with ability to dive deep into architecture, engineering, security, data, operations, and business process details.
• Collaborative communicator who can influence across business, technology, risk, and governance teams.
• Meticulous planner, systems thinker, constructive challenger, and talent builder who raises standards while building trust.

Benefits

Benefits

We are proud to offer our full-time regular employees a robust benefits suite that includes:

• Competitive base salary plus incentive plans for eligible team members
• 401(K) retirement plan that includes a company match of up to 6% of your eligible salary
• Free basic life and AD&D, long-term disability and short-term disability insurance
• Medical, dental and vision plans to meet your unique healthcare needs
• Wellness incentives
• Generous time off program that includes personal, holiday and volunteer paid time off
• Flexible work schedules and hybrid/remote options for eligible positions
• Educational assistance