VP, AI - First IT and Transformation

Department: Information Technology Job Description: 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 will partner with business leaders to identify and deliver AI-enabled improvements in areas such as underwriting, claims, operations, finance, customer experience, and employee productivity. The role will also guide the creation of AI-First platforms, establish AI-first engineering practices, support adoption of AI across the software development lifecycle and IT operations, and enable 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. Over time, this team will collaborate closely with Applications, Engineering, Infrastructure, Operations, Security, Data, Architecture, Risk Governance, and business teams to help scale AI-First practices across the broader organization. The team is intended to serve as a catalyst, not a silo, helping TMG develop future-ready technology capabilities while maintaining strong security, privacy, governance, and operational discipline. TMG is evolving its IT operating model across Core IT, Modernization IT, and Future IT. Future IT will build the next generation IT operating model where AI is embedded into how the organization builds technology, runs operations, supports employees, and enables business capabilities. Work Arrangement: Employees who live within 30 miles of the TMG home office are expected to follow a hybrid or in-office schedule. The initial training period may require additional in‑office days. 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 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. Qualifications: 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. Pay Range: Anticipated Hiring Range: $230,000 - $270,000 annual base salary depending on experience, qualifications, and geographic location $250,000 - $290,000 annual base salary depending on experience, qualifications, and geographic location in CA, CT, MA, NJ, NY, and PA 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 Equal Opportunity Employer The Mutual Group is an Equal Opportunity Employer. It is our policy to recruit, hire, train and promote individuals in all job classifications without regard to race, color, religion, sex, national origin, age, veteran status, disability, sexual orientation, gender identity or any other characteristic protected by law. Know Your Rights: Workplace Discrimination is Illegal Your Rights Under USERRA Applicants requiring a reasonable accommodation due to a disability at any stage of the employment application process should contact View email address on click.appcast.io. Employment Verification The Mutual Group participates in the E-Verify program and will provide the federal government with your Form I-9 information to confirm that you are authorized to work in the U.S. You are protected from employment discrimination based on your citizenship status and national origin. E-Verify Program Overview E-Verify Participation Poster All offers of employment are contingent upon the successful completion of a background check. #TMG The Mutual Group is an Equal Opportunity Employer. It is our policy to recruit, hire, train and promote individuals in all job classifications without regard to race, color, religion, sex, national origin, age, veteran status, disability, sexual orientation, gender identity or any other characteristic protected by law. Know Your Rights: Workplace Discrimination is Illegal Your Rights Under USERRA Applicants requiring a reasonable accommodation due to a disability at any stage of the employment application process should contact View email address on click.appcast.io. The Mutual Group participates in the E-Verify program and will provide the federal government with your Form I-9 information to confirm that you are authorized to work in the U.S. You are protected from employment discrimination based on your citizenship status and national origin. All offers of employment are contingent upon the successful completion of a background check.