Technology Strategy & Integration Director

Shepherd Insurance LLC; Carmel (IN); On-site; USD 140,000 - 190,000; Full time

Job summary

Shepherd Insurance LLC in Carmel, IN seeks a Director of Technology Strategy and Execution to translate priorities across IT, Data, Security, AI, and vendors into clear plans and measurable progress. You will partner with IT leadership to strengthen execution discipline while aligning technology initiatives with business goals.

This leadership role focuses on acquisition integration, governance, and credible reporting, building repeatable practices and driving AI-enabled transformations from

Qualifications

• Bachelor's degree in Information Technology, Computer Science, or related field preferred, or equivalent professional experience.
• Eight+ years of experience in program management, strategic execution, PMO operations, or technology leadership.
• Experience in insurance, financial services, or another regulated industry preferred.
• PMP certification or equivalent preferred.

Responsibilities

• Lead the execution framework for acquisition integration, including workstream planning, technology readiness, stakeholder alignment, decision tracking, and lessons learned.
• Build repeatable integration practices that preserve strengths of acquired teams while reducing duplicated tools, contracts, and effort.
• Lead cross-functional initiatives from intake through completion, with clear ownership, dependencies, decision paths, and follow-through.
• Establish execution standards, operating cadence, governance, and decision-ready reporting for shared priorities across IT, Data, Security, vendors, and business partners.
• Track execution performance, issue resolution, and accountability across managed service, security, and technology partners.
• Partner with IT leadership to improve service-management, documentation, asset-management, workflow, and reporting practices, including ConnectWise.
• Partner with the data team to bring structure, prioritization, and execution discipline to analytics, migration, data ownership, quality, and reporting priorities.
• Identify, prioritize, and enable practical AI use cases with clear ownership, readiness, governance, and adoption plans.

Skills

Cross-functional leadership

Stakeholder partnership

Executive communication

Project management

PMO/implementation

Education

Bachelor's degree in IT / CS / related field

PMP certification (preferred)

Tools

ConnectWise

Microsoft 365

Office Suite

Job description

Shepherd Insurance LLC in Carmel, IN seeks a Director of Technology Strategy and Execution to translate priorities across IT, Data, Security, AI, and vendors into clear plans and measurable progress. You will partner with IT leadership to strengthen execution discipline while aligning technology initiatives with business goals.

This leadership role focuses on acquisition integration, governance, and credible reporting, building repeatable practices and driving AI-enabled transformations from