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

Requirements

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

Benefits
Oakbridge Insurance Agency offers a friendly and flexible work environment and first‑class benefits to meet the needs of you and your family. Benefits include a 401(k) 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.

Equal Employment Opportunity
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.

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