Assistant IT Director

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Location / Remote: Hybrid in Kissimmee, FL, 34744 (3 days per week onsite).

Employment Type: Permanent / Direct Hire.

Benefits

• 100% employer-paid health benefits for employees (83% employer contribution for dependents)
• Pension plan for long-term retirement security
• Employer-paid life insurance coverage
• Short-term and long-term disability insurance provided at no cost
• Comprehensive benefits supporting long-term stability and employee well-being

Compensation: Competitive Salary (based on experience)

This role is a pivotal leadership position within the IT department, responsible for managing legacy infrastructure while driving modernization and cloud adoption strategies. The Assistant IT Director will play a key role in advancing technology initiatives, integrating emerging technologies like AI, and preparing for significant transitions such as an ERP replacement. This position offers substantial growth opportunities, including succession planning to step into the IT Director role within the next few years.

Responsibilities

• Oversee operations for a large legacy infrastructure footprint, including 550 virtual servers, dual data centers, 80 connected facilities via dark fiber, and a Dell/VMware/Microsoft/Cisco stack.
• Manage on-premise COTS application environments and ensure operational efficiency.
• Drive cloud adoption strategies, currently at 25%, and modernize software development approaches for legacy applications.
• Integrate AI into small-to-medium custom-built applications and enhance data integration, analysis, and reporting capabilities.
• Lead preparation and execution of major transitions, including an ERP/financial software replacement.
• Build strong relationships with the executive team and department leaders to align IT strategies with organizational goals.
• Manage large IT budgets ranging from $26M $30M annually and participate in the budget planning process.
• Provide strategic leadership and mentorship to ensure readiness for succession into the IT Director role.

Required Skills

• Minimum 7 years in a leadership role within IT, with demonstrated experience managing large-scale infrastructure and modernization initiatives.
• Proven ability to direct operations for legacy systems and execute cloud strategies effectively.
• Strong appetite for emerging technologies, particularly AI integration and advanced data capabilities.
• Experience leading significant transitions, such as ERP replacements or similar large-scale implementations.
• Leadership maturity and strategic vision to step into the IT Director role within the next couple of years.
• Strong executive presence and relationship-building skills, with the ability to collaborate effectively with senior leadership.
• Hands-on experience managing IT budgets of $26M-plus annually.

Preferred Skills

• Experience in local government to facilitate public sector transitions.
• Background in supporting project teams, reviewing project requests, and collaborating with county leadership on strategic initiatives.