Senior Director of Underwriting Technology Transformation

The Senior Director of Underwriting Technology Transformation role is seeking a transformation executive with a strong background in technology leadership and underwriting. Key responsibilities include:

1. Lead the enterprise technology transformation strategy for underwriting operating models, decisioning systems, and technology products.
2. Drive innovation initiatives that modernize underwriting capabilities and replace outdated technologies with scalable, future-focused solutions.
3. Define technical direction across technology teams, ensuring alignment between product roadmaps, business objectives, and enterprise architecture.
4. Partner with underwriting, actuarial, finance, sales, product management, analytics, and technology leadership to deliver transformation programs.
5. Embed data-driven insights, AI-enabled decisioning, and advanced analytics into underwriting workflows to improve efficiency and financial performance.
6. Establish enterprise standards for underwriting tools, data integration, analytics capabilities, and technology governance.
7. Manage and develop high-performing teams through coaching, performance management, talent development, and operational leadership.
8. Collaborate with stakeholders to define technology portfolios, investment priorities, roadmaps, and transformation initiatives.
9. Influence executive leadership by providing strategic recommendations and driving alignment across complex organizational structures.
10. Ensure successful execution and adoption of technology products that deliver measurable business value.

Requirements include:

• 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.
• Prior 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.

Benefits include:

• 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.
• Retail 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.
• A collaborative environment focused on innovation, professional growth, and meaningful business impact.
• Opportunity to influence the future of underwriting technology and decision-making capabilities.

How Jobgether Works: We use an AI-powered matching process to ensure your application is reviewed quickly, objectively, and fairly against the role's core requirements. Our system identifies the top-fitting candidates, and this shortlist is then shared directly with the hiring company. The final decision and next steps (interviews, assessments) are managed by their internal team.