VP, AI – IT and Transformation

The Mutual Group

. Define and lead TMG’s enterprise AI strategy in partnership with the CITO, business executives, technology leaders, and risk governance partners.

Posted 5/17/2026full-timeIllinois, Iowa, Massachusetts, Texas, Washington • 🇺🇸 United StatesLead💰 $230,000 - $270,000 per yearWebsite

Tech Stack

Tools & technologies

CloudCyber SecurityMicroservicesSDLC

About the role

Key responsibilities & impact

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.
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.
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.
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.

Requirements

What you’ll need

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.

Benefits

Comp & perks

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

ATS Keywords

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Applicant Tracking System Keywords

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Hard Skills & Tools

AI strategymachine learningGenerative AIautomationadvanced analyticsmodel lifecycle practicesprompt engineeringworkflow orchestrationobservabilitycloud platforms

Soft Skills

leadershipcommunicationcollaborationstrategic thinkingproblem-solvingorganizational skillsadaptabilitythought leadershiprisk managementdelivery governance

Certifications

Bachelor’s degree in Computer ScienceBachelor’s degree in EngineeringBachelor’s degree in Information SystemsBachelor’s degree in Data ScienceMaster’s degreeMBA