Senior Director of Underwriting Technology Transformation

Senior Director Of Underwriting Technology Transformation

This role offers the opportunity to lead enterprise-wide technology transformation initiatives that redefine how underwriting decisions are made and delivered. The position focuses on building scalable, data-driven technology ecosystems that improve underwriting productivity, pricing accuracy, and business performance. You will partner with senior leaders across technology, underwriting, actuarial, finance, and product teams to drive meaningful innovation. The role combines strategic vision, technology leadership, operational transformation, and deep industry expertise.

You will shape the future of underwriting platforms by integrating analytics, automation, and advanced decisioning capabilities into daily workflows. This is an impactful leadership opportunity for a transformation executive who thrives in complex environments and delivers measurable business outcomes.

Accountabilities:

• Lead the enterprise technology transformation strategy for underwriting operating models, decisioning systems, and technology products.
• Drive innovation initiatives that modernize underwriting capabilities and replace outdated technologies with scalable, future-focused solutions.
• Define technical direction across technology teams, ensuring alignment between product roadmaps, business objectives, and enterprise architecture.
• Partner with underwriting, actuarial, finance, sales, product management, analytics, and technology leadership to deliver transformation programs.
• Oversee the development and deployment of analytics tools, workflow automation, and decision-support capabilities that improve underwriting outcomes.
• Embed data-driven insights, AI-enabled decisioning, and advanced analytics into underwriting workflows to improve efficiency and financial performance.
• Establish enterprise standards for underwriting tools, data integration, analytics capabilities, and technology governance.
• Lead technology evaluations, including build-versus-buy decisions, vendor assessments, and platform selection strategies.
• Manage and develop high-performing teams through coaching, performance management, talent development, and operational leadership.
• Collaborate with stakeholders to define technology portfolios, investment priorities, roadmaps, and transformation initiatives.
• Influence executive leadership by providing strategic recommendations and driving alignment across complex organizational structures.
• Ensure successful execution and adoption of technology products that deliver measurable business value.

• 10+ years of experience in leadership roles managing multi-layer teams and complex technology initiatives.
• 7+ years of experience leading technology transformation programs and enterprise-scale change initiatives.
• 5+ years of experience in underwriting, insurance, revenue generation, or related business domains.
• Bachelor's degree or equivalent combination of relevant experience and education required.
• Master's degree in Business Administration, Actuarial Science, Mathematics, Statistics, Analytics, Technology, or a related field preferred.
• Strong expertise in enterprise transformation leadership, technology operating models, and product lifecycle management.
• Deep understanding of underwriting, pricing, risk management, and insurance technology environments.
• Experience leveraging analytics, AI-enabled decisioning, and data-driven solutions to improve business outcomes.
• Strong executive communication skills with the ability to influence senior stakeholders and align cross-functional teams.
• Proven experience managing technology vendors, external partners, and strategic platform decisions.
• Strong strategic thinking, problem-solving abilities, and ability to operate effectively in highly matrixed organizations.

• Competitive base salary range of $169,500 to $286,700 annually, based on qualifications, experience, market factors, and business considerations.
• Remote work flexibility with occasional onsite requirements.
• Comprehensive healthcare benefits package.
• Retirement and financial wellness programs.
• Paid time off and employee wellbeing resources.
• Opportunity to lead high-impact transformation initiatives at enterprise scale.
• Exposure to advanced analytics, automation, and AI-driven technology solutions.
• Collaborative environment focused on innovation, professional growth, and meaningful business impact.
• Opportunity to influence the future of underwriting technology and decision-making capabilities.