IT Director (Hybrid)

The opportunity

We are looking for an IT Director to lead the modernization of our underwriting platform and policy administration capabilities. The Director will partner across business functions to evolve legacy systems into a modern, cloud‑enabled, scalable platform that enhances speed to market, underwriting efficiency, resiliency, and data‑driven decision‑making. This role blends technology leadership with business transformation and is based in either Farmington, CT; Canton, MA; Boston, MA; or Raleigh, NC on a hybrid schedule.

Responsibilities

• Define and execute the strategy to modernize and transform underwriting and policy administration platforms.
• Lead the 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, improve decision‑making, and deliver modern underwriting capabilities.
• Enable configurable, reusable, and scalable platform services.
• Lead policy/data migration, including conversion, validation, and cutover planning.
• Ensure strong data quality, traceability, and regulatory compliance.
• Oversee integration with claims, billing, data, and digital ecosystems.
• Drive cloud‑enabled, secure, and resilient platform architecture aligned to enterprise standards.
• 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 sustainability.
• 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.
• Lead adoption of modern ways of working across technology and business teams.
• Build and lead high‑performing engineering and delivery teams.
• Manage vendors, partners, and technology investments.
• Develop capabilities across cloud, platform engineering, and AI.
• Ensure adherence to regulatory, security, and audit requirements.
• Establish strong operational governance and production readiness.
• Balance innovation with stability and risk management.

The expertise you bring

• 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.

Salary & Benefits

Salary ranges are target base salary $225,000 - $263,000, based on location, role, experience, and skillset. Additional benefits include:

• Comprehensive medical, dental and vision insurance with no waiting period.
• Competitive paid time off programs.
• 401(k) savings with up to 12% annual contributions.
• Mental health support, life and disability insurance, paid parental leave, and other voluntary benefits.
• Full bonus potential for eligible employees.

This position will remain posted until a final candidate is selected. Once the role is filled, the job posting will be removed.

Equal Opportunity Employer
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