Director of Digital Transformation

The Director of Digital Transformation plays a critical leadership role in shaping and executing Oakbridge Insurance’s 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
• 8+ years of experience in roles bridging operations and technology (e.g., digital transformation, program leadership, process improvement or enterprise systems

• Proven ability to lead complex, cross-functional initiatives and drive alignment across stakeholders

• Strong ability to translate business needs into actionable technical and operational plans

• Demonstrated experience managing large-scale transformation or change initiatives

• Technical fluency with systems, data and architecture concepts sufficient to collaborate with IT and engineering teams

• Excellent leadership, communication and problem-solving skills

• Ability to operate effectively in ambiguous environments and bring clarity to complex challenges

Preferred Education & Experience

• Experience in the insurance or financial services industry

• Background in AI, automation or digital transformation initiatives

• Familiarity with operational performance metrics and continuous improvement methodologies

• Exposure to governance, compliance and regulatory environments

• Experience supporting M&A integration or multi-entity operations

Deeply Rooted to Serve

Oakbridge Insurance Agency is a new kind of insurance and risk management agency with the mission to transform and elevate the way business is done in our industry.

For over 100 years, the founding firms of Oakbridge worked alongside each other in small towns and cities throughout the Southeast, cultivating similar company cultures and best practices, and earning each other's respect in the industry. They envisioned a way to impact the future of insurance and formed Oakbridge Insurance Agency on January 1, 2021. Since forging this different path, we are proud to have added additional partners to Oakbridge who reflect our vision, demonstrate our core values, and share our commitment to doing what is right for our friends and neighbors.

Our most important asset is our people. We offer a friendly and flexible work environment and offer first-class benefits to meet the needs of you and your family. Benefits include a 401k plan with immediate participation, company match, and immediate 100% vesting. Company-paid benefits include life insurance and short- and long-term disability. We have a strong health insurance plan and many supplemental, voluntary offerings.

Oakbridge Insurance is an equal opportunity employer that is committed to diversity and inclusion in the workplace. We prohibit discrimination and harassment of any kind based on race, color, sex, religion, sexual orientation, national origin, disability, genetic information, pregnancy, or any other protected characteristic as outlined by federal, state, or local laws.

This policy applies to all employment practices within our organization, including hiring, recruiting, promotion, termination, layoff, recall, leave of absence, compensation, benefits, training, and apprenticeship. Oakbridge Insurance makes hiring decisions based solely on qualifications, merit, and business needs at the time.

For more information visit our website:

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