Director of Technology Strategy & Execution

As Director of Technology Strategy and Execution, you will help Shepherd Insurance turn shared priorities across IT, Data, Security, AI, vendors, and acquired organizations into clear plans, decisions, accountability, and measurable progress. This role partners closely with technology and business leaders to strengthen execution discipline, improve integration practices, and move strategic initiatives from discussion to completion.

What You Will Do

Lead the execution framework for acquisition integration, build repeatable integration practices, lead cross-functional initiatives, establish execution standards, track execution performance, and review inherited and overlapping technology.

Why It Might Be a Fit

This role requires strong cross-functional leadership and stakeholder partnership skills, ability to influence without direct authority, and experience leading complex initiatives and managing vendor relationships.

Requirements

• Strong cross-functional leadership and stakeholder partnership skills across technical and business teams.
• Ability to influence without direct authority, create practical operating discipline, and move complex work forward through clear ownership, decisions, and follow-through.
• Demonstrated experience leading complex initiatives, improving processes, and building governance or operating-model practices.
• Experience managing vendor, managed service, or security-partner relationships and holding partners accountable to outcomes.
• Experience supporting mergers, acquisitions, or post-acquisition integration, preferred.
• Familiarity with service-management, workflow, and reporting platforms, including ConnectWise or similar tools, preferred.
• Strong written and verbal communication skills, with the ability to simplify complex issues into clear decisions, actions, and executive-ready updates.
• Strong proficiency with Microsoft systems, including Active Directory, Microsoft 365 and Office Suite, Internet Browsers and ticketing systems.
• Ability to lift 50 pounds or more.
• Travel required between office locations.