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IT Director

Kavaliro, Kissimmee, FL, United States


IT Director We are seeking an experienced and strategic IT Director to lead the management and modernization of a complex enterprise technology environment. This role will oversee core infrastructure operations while driving technology initiatives that improve scalability, security, and operational efficiency.

The ideal candidate will bring strong leadership experience managing large-scale infrastructure environments while also guiding modernization efforts including cloud adoption, enterprise systems transformation, and emerging technology integration.

Key Responsibilities Enterprise Infrastructure Leadership

Provide leadership and oversight for a complex enterprise infrastructure environment including 550+ virtual servers across dual data centers.

Support network connectivity and technology operations across 80+ connected facilities via dark fiber infrastructure.

Manage enterprise systems built on a Dell / VMware / Microsoft / Cisco technology stack.

Ensure high availability, reliability, and security across enterprise platforms and commercial off-the-shelf (COTS) applications.

Cloud Strategy & Technology Modernization

Lead initiatives to expand cloud adoption beyond the current 25% cloud footprint and guide the organization toward a modern hybrid infrastructure strategy.

Develop roadmaps for modernizing legacy applications and improving infrastructure scalability and resilience.

Support modernization of development practices and enterprise application architecture.

AI, Data & Digital Innovation

Identify opportunities to integrate AI capabilities into internally developed applications.

Enhance enterprise data integration, analytics, and reporting capabilities to support data-driven decision making.

Evaluate and implement emerging technologies that improve operational efficiency.

Enterprise Systems Transformation

Lead the planning and execution of a major ERP and financial system replacement initiative.

Work with cross-functional stakeholders to support system selection, implementation, and organizational adoption.

Ensure integration with existing enterprise platforms and operational workflows.

Leadership & Strategic Planning

Partner with senior leadership to develop long-term IT strategy and technology roadmaps.

Provide leadership and mentorship to IT teams responsible for infrastructure, applications, and operations.

Oversee vendor relationships, technology investments, and operational performance.

Qualifications Required

10+ years of progressive IT leadership experience

Experience managing large-scale enterprise infrastructure environments

Strong understanding of hybrid environments combining on-premise infrastructure and cloud platforms

Proven experience leading technology modernization initiatives

Experience overseeing complex enterprise software implementations

Strong leadership, communication, and stakeholder management skills

Preferred

Experience supporting multi-site organizations with distributed infrastructure

Experience with ERP or financial system implementations

Experience leading cloud transformation initiatives

Familiarity with data analytics platforms and AI-enabled applications

Kavaliro provides Equal Employment Opportunities to all employees and applicants. All qualified applicants will receive consideration for employment without regard to race, color, religion, age, sex, national origin, disability status, genetics, protected veteran status, sexual orientation, gender identity or expression, or any other characteristic protected by federal, state, or local laws. Kavaliro is committed to the full inclusion of all qualified individuals. In keeping with our commitment, Kavaliro will take the steps to assure that people with disabilities are provided reasonable accommodations. Accordingly, if reasonable accommodation is required to fully participate in the job application or interview process, to perform the essential functions of the position, and/or to receive all other benefits and privileges of employment, please respond to this posting to connect with a company representative.

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