Director of Digital Transformation

The Director of Digital Transformation plays a critical leadership role in shaping and executing Oakbridge Insurances digital and operational strategy. This individual is responsible for translating complex business challenges into scalable, technology-enabled solutions that drive measurable impact across the organization. Working closely with the CIO, IT leadership and business stakeholders, the Director will lead cross-functional initiatives focused on AI-enabled workflows, process optimization and system integration. This role ensures alignment between business objectives and technical execution while fostering organizational readiness, adoption and continuous improvement. Work Performed Lead enterprise digital transformation initiatives, prioritizing efforts that improve efficiency, accuracy and scalability Translate business workflows into clear requirements for automation, AI-assisted processes and system enhancements Drive program leadership across multiple domains, maintaining momentum, resolving decisions and ensuring accountability Partner with business leaders across operations, finance, compliance and IT to align priorities and ensure successful execution Establish and track key performance metrics (e.g., cycle time, throughput, cost-to-serve) to measure impact and guide decision making Oversee operational design and process re-engineering to support scalable, technology-enabled workflows Support governance, risk and compliance considerations related to new systems and automation initiatives Lead change management efforts including communication, training and adoption strategies for new tools and processes Collaborate with engineering and IT teams to ensure solutions are feasible, scalable and aligned with enterprise architecture Assist with integration efforts related to acquisitions, data migration and system consolidation