Vice President, AI - First IT and Transformation

Location: New York

As the Vice President, AI-First IT and Transformation, you will play a key role in supporting Guide One 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.