Executive Connectwise Jobs in Indiana (NOW HIRING)

Description

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.

As Director of Technology Strategy and Execution, you will help Shepherd 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. This role does not assume ownership of IT service delivery, technical operations, or day-to-day support functions.

This role works closely with the Director of IT, CIO, and business leaders to collaborate and strengthen technology efforts.

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.

WORKING CONDITIONS/PHYSICAL DEMANDS:

Work environment characteristics and physical demands described here are representative of those that must be met by an employee to successfully perform the essential functions of this job. Reasonable accommodations may be made to enable individuals with disabilities to perform the essential functions. 

While performing the duties of this job, the employee is occasionally required to stand; walk; sit; use hands to finger, handle, or feel objects, tools or controls; reach with hands and arms; climb stairs; balance; stoop; kneel, crouch or crawl; talk or hear; taste or smell. The employee must occasionally lift and/or move up to 25 pounds. Specific vision abilities required by the job include close vision, distance vision, color vision, peripheral vision, depth perception, and the ability to adjust focus. While performing the duties of this job, the employee is not exposed to weather conditions. The noise level in the work environment is usually moderate.