Tech Strategy & Execution Leader - M&A, AI & Governance

Shepherd Insurance; Carmel (IN); On-site; USD 120,000 - 190,000; Full time

Job summary

Shepherd Insurance seeks a Director of Technology Strategy and Execution to translate shared IT, data, security, AI, and vendor priorities into actionable plans. You will collaborate with IT, CIO, and business leaders to strengthen execution discipline and move strategic initiatives from discussion to completion.

This role excludes day‑to‑day IT service delivery. The role emphasizes leading acquisition integration efforts, building repeatable practices, and guiding governance while aligning

Qualifications

• Bachelor’s degree in Information Technology, Computer Science, or related field preferred, or equivalent professional experience.
• Eight+ years’ 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.
• Strong cross‑functional leadership and stakeholder partnership skills across technical and business teams.
• Ability to influence without direct authority and drive clear ownership and decisions.

Responsibilities

• Lead the execution framework for acquisition integration, including workstream planning and stakeholder alignment.
• Build repeatable integration practices that preserve strengths while reducing duplicated tools and effort.
• Lead cross‑functional initiatives from intake to completion with clear ownership and reporting.
• Establish execution standards, governance, and decision‑ready reporting for shared priorities across IT, Data, Security, and vendors.
• Track execution performance, issue resolution, and accountability across managed service and technology partners.
• Review inherited technology, vendor agreements, and renewals to identify consolidation and value‑recovery opportunities.
• Partner with IT leadership to improve service‑management, documentation, asset‑management, and reporting practices.

Skills

Cross‑functional leadership

Influence without authority

Strategic execution

Vendor management

Acquisition integration

Communication

Service‑management tooling

Microsoft 365 tools

Education

Bachelor’s degree in IT/CS or related field

PMP certification or equivalent (preferred)

Tools

ConnectWise

Active Directory

Microsoft 365

Job description

Shepherd Insurance seeks a Director of Technology Strategy and Execution to translate shared IT, data, security, AI, and vendor priorities into actionable plans. You will collaborate with IT, CIO, and business leaders to strengthen execution discipline and move strategic initiatives from discussion to completion.

This role excludes day‑to‑day IT service delivery. The role emphasizes leading acquisition integration efforts, building repeatable practices, and guiding governance while aligning