Director of Information Technology

The Opportunity: We are seeking a hands-on Director of Information Technology to lead all technology functions for our organization while serving as a member of the executive leadership team. This is a unique opportunity for an experienced IT professional who wants to remain technically involved while also helping shape organizational strategy. As our primary internal IT resource and one-person IT department, you will manage the day-to-day technology environment, cybersecurity, vendors, infrastructure, and long-term technology planning. The right candidate will be equally comfortable discussing technology strategy with executive leadership, evaluating cybersecurity risks, managing vendors, administering systems, and helping an employee solve a technical problem.50 Years of Safety and Service - 2026 marks Diggers Hotline's 50th anniversary. Since 1976, we have served as a critical safeguard for Wisconsin's communities, contractors, homeowners, and buried facility owners by helping prevent damage to underground infrastructure and supporting safe excavation. Every locate request we process represents an opportunity to prevent an accident, avoid a service disruption, and help keep a community safe. Technology is essential to delivering that mission reliably today—and to preparing Diggers Hotline for the future. As Director of Information Technology, you'll have an important role in helping us build on that 50-year legacy.

What You'll Do: Manage and support computers, applications, cloud services, networks, telecommunications, and IT infrastructure. Provide hands-on technical support and troubleshooting for employees. Administer user accounts, permissions, email, collaboration tools, and business systems. Lead cybersecurity, access management, endpoint protection, patching, backups, and technology risk management. Maintain disaster recovery and technology-related business continuity plans. Develop the organization's long-term technology roadmap. Manage the IT budget, technology lifecycle planning, and capital investments. Manage technology vendors, consultants, contracts, and service providers. Evaluate and recommend new technologies and system improvements. Develop and maintain IT policies, procedures, standards, and documentation. Participate in executive leadership and organizational strategic planning.

What We're Looking For: 5+ years of progressively responsible IT experience. Bachelor's degree in IT, Computer Science, Information Systems, Cybersecurity, or a related field—or equivalent education and experience. Strong hands-on experience with users, endpoints, networks, cloud services, business applications, and IT infrastructure. Experience with cloud infrastructure platforms such as Azure. Working knowledge of cybersecurity, identity/access management, endpoint protection, backups, disaster recovery, and business continuity. Strong troubleshooting and analytical skills. Ability to communicate technical issues and risks clearly to nontechnical audiences. Experience managing technology vendors and service providers.

Nice to have: Experience as the primary IT professional in a small or midsized organization, technology budgeting and planning, scripting/automation, data analytics, or a mission-critical environment. You’ll Be a Great Fit If You...Still enjoy being hands-on with technology. Take ownership of problems through resolution. Can move comfortably between troubleshooting and strategic discussions. Work well independently and know when outside expertise is needed. Think proactively about cybersecurity, reliability, and risk. Want bothhands-on technical responsibility and a seat at the leadership table. Compensation Anticipated hiring range: $110,000–$130,000 annually, based on qualifications and experience, plus eligibility for annual performance compensation. This is an opportunity to directly own an organization's technology environment while helping shape its technology strategy for the future.