IT Director (Hybrid)

About the role

The opportunity is for an IT Director to join our Corporate IT team based in our Farmington, CT; Canton, MA; Boston, MA or Raleigh, NC offices on a hybrid schedule. This role is responsible for leading the modernization of our underwriting platform and associated policy administration capabilities.

Responsibilities

• Define and execute on the strategy to modernize and transform our underwriting and policy administration platform
• Lead transformation of legacy systems into a scalable, cloud-enabled platform
• Drive phased delivery to minimize business disruption and manage risk
• Partner with underwriting and product leaders to streamline workflows and improve decision-making
• Deliver modern underwriting capabilities (eligibility, pricing, referrals, portfolio management)
• Enable configurable, reusable, and scalable platform services
• Migrate, integrate, and ensure data quality
• Lead cloud architecture and engineering excellence
• Drive modern engineering practices (API-first, event-driven, DevSecOps, CI/CD)
• Align to enterprise architecture standards and reusable platform services
• Product model and delivery execution
• Transition to a product-focused operating model with clear ownership and outcomes
• Lead roadmap delivery, prioritization, and cross-team coordination
• Balance speed, quality, and long-term platform sustainability
• Ai & Automation Enablement
• Introduce AI and automation to improve underwriting efficiency and decision support
• Integrate data-driven insights into workflows
• Ensure responsible AI adoption with clear business value
• Change & Transformation Leadership
• Lead adoption of modern ways of working across technology and business teams
• Drive alignment on roadmap, priorities, and business readiness
• Act as a visible transformation leader across the organization
• Talent, Vendor & Financial Management
• Build and lead high-performing engineering and delivery teams
• Manage vendors, partners, and technology investments
• Develop capabilities across cloud, platform engineering, and AI
• Risk, Compliance & Operations
• Ensure adherence to regulatory, security, and audit requirements
• Establish strong operational governance and production readiness
• Balance innovation with stability and risk management

Requirements

12+ years of progressive technology leadership experience, including significant experience in enterprise application engineering, platform modernization, or insurance technology transformation.

5+ years leading managers and/or large cross-functional technology organizations with accountability for delivery, budget, and talent outcomes.

Proven experience leading modernization of policy administration, underwriting, or core insurance platforms in a carrier environment.

Experience delivering in complex, regulated environments requiring strong governance, risk management, and audit/compliance discipline.