Directory of Technology Strategy & Execution

Job Summary

This is an ideal opportunity to work at a growing organization with a strong family culture. Shepherd Insurance is a privately-owned insurance agency that has delivered risk management solutions since 1977. With a wide variety of insurance and financial products, we are among the largest independent agencies in the country.

Roles And 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 the 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.
• Review inherited and overlapping technology, vendor agreements, and renewals to identify consolidation, negotiation, and value-recovery opportunities.
• Partner with IT leadership to improve service-management, documentation, asset-management, workflow, and reporting practices, including ConnectWise and related tools, while informing long-term platform decisions.
• Partner with the data team to bring structure, prioritization, and execution discipline to analytics, migration, data ownership, quality, and reporting priorities.
• Partner with business and technology leaders to identify, prioritize, and enable practical AI use cases with clear ownership, readiness, governance, and adoption plans.
• Capture and maintain the processes, decision paths, onboarding practices, and institutional knowledge that preserve Shepherd’s relationship-driven service as the organization grows.
• Build trusted relationships across business and technology leadership and foster a culture of accountability, collaboration, and continuous improvement.
• Perform other related duties as assigned.

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.

Education And Experience Requirements

• Education requirement: Bachelor’s degree in Information Technology, Computer Science, or related field preferred, or equivalent professional experience.
• Experience: At least eight (8) years’ experience in a similar position is desirable specific to program management, strategic execution, PMO operations, business transformation, or technology leadership, including cross-functional leadership responsibility.
• Experience in insurance, financial services, or another regulated industry, preferred.
• PMP certification or equivalent, preferred.