Telecommute Director Technology Strategy Jobs in Wisconsin

Purpose and Summary The Information Technology Director provides executive leadership and strategic direction for Sheboygan County's Information Technology Department, ensuring the effective, secure, and efficient delivery of Countywide technology services in support of organizational goals and public service objectives. This position is responsible for establishing the County's information technology vision, governance structure, and long-term strategic roadmap. Working closely with the County Administrator, County Board, department heads, and other stakeholders, the IT Director oversees technology planning, operations, cybersecurity, compliance, budgeting, and enterprise systems management.

The position ensures that technology investments are aligned with County priorities, regulatory requirements, and best practices, while promoting innovation, operational resilience, intergovernmental collaboration, and continuous improvement across County services. Essential Duties Strategy and governance: Establish the County's IT vision, governance framework, master plan, and long-term strategic roadmap. Secure, dependable operations: Oversee Countywide infrastructure, networks, servers, applications, telecommunications, end-user systems, and enterprise platforms throughout their lifecycles.

Cybersecurity and compliance: Direct policies and standards for cybersecurity, data protection, disaster recovery, business continuity, incident response, architecture, and service delivery. Regulatory leadership: Serve as the County's HIPAA Security Officer and Security Officer for state computer applications, and partner with the Sheriff's Department on CJIS compliance. Investment and portfolio management: Prioritize and oversee technology projects; develop operating and capital budgets; manage contracts, purchasing, allocations, and business cases; and report results to County leadership and the County Board.

People and performance: Lead organizational design, workforce planning, recruitment, performance management, staff development, succession planning, and a culture of accountability and service excellence. Innovation and partnership: Evaluate emerging technologies, improve service delivery, and advance cooperative initiatives with municipalities, school districts, vendors, and other partners. Qualifications Education and Experience Bachelor's degree from an accredited college or university in Information Systems, Computer Science, or a related field.

Eight years of experience working directly with client-server and multi-site infrastructure, hardware and software, and systems development, including five years of supervisory experience. A combination of education and experience may be considered. Valid Wisconsin driver's license.

Knowledge, Skills, and Abilities Executive-level judgment and the ability to translate County priorities into practical technology strategies, policies, investments, and operating plans. Strong knowledge of enterprise infrastructure, networks, operating systems, virtual server environments, cybersecurity, data privacy, regulatory requirements, and technology lifecycle management. Demonstrated success leading professional and technical teams, complex projects, budgets, contracts, vendors, and organizational change.

Clear, audience-centered communication with elected officials, executive leaders, department heads, technical teams, partners, regulatory agencies, and the public. Strong analytical, financial, problem-solving, and decision-making skills, including cost-benefit and return-on-investment evaluation. A collaborative, service-oriented leadership style grounded in integrity, discretion, accountability, resilience, and continuous improvement.

Work Environment & Physical Requirements Work is performed primarily in an office environment, with occasional work in data centers, server rooms, telecommunications closets, and other technical areas. The role requires prolonged concentration and computer use; occasional lifting or moving of equipment or supplies up to approximately 25 pounds; and travel between County facilities or meetings. Evening, weekend, or after-hours work may be required for maintenance, security incidents, emergencies, or critical operations.

Reasonable accommodations may be made to enable individuals with disabilities to perform the essential functions.