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Head of IT / Director of Digital Innovation

Orlando, FL 32801

Posted: 06/05/2026 Industry: IT Job Number: 55297

Job Description

Position Overview
We are seeking a forward-thinking IT Leader to drive digital innovation and technology strategy for a growing organization. This role is ideal for a hands-on strategic leader who can balance vision with execution.

This individual will play a critical role in elevating the company’s technology capabilities, identifying opportunities for digital transformation, and aligning IT initiatives with business growth objectives.

Success in this position requires creativity, resourcefulness, and the ability to influence across the organization while operating in a lean, fast-moving environment.
Key Responsibilities Strategic Leadership
  • Develop and execute a practical, scalable IT and digital innovation roadmap
  • Partner with executive leadership to align technology initiatives with business goals
  • Identify opportunities to leverage technology for efficiency, revenue growth, and competitive advantage
  • Serve as a trusted advisor on digital trends, automation, AI, and emerging technologies
Digital Innovation & Transformation
  • Lead initiatives that modernize systems, processes, and customer experiences
  • Evaluate and implement tools that improve productivity and operational effectiveness
  • Introduce data-driven decision-making and reporting capabilities where appropriate
  • Drive a culture of innovation across the organization
IT Operations Oversight
  • Oversee day-to-day IT operations, including internal systems and external vendors
  • Ensure reliability, performance, and security of systems and infrastructure
  • Manage vendor relationships, contracts, and outsourced services when necessary
  • Establish and maintain appropriate cybersecurity practices and risk mitigation
Hands-On Leadership
  • Remain operationally involved when needed—this role blends leadership with execution
  • Prioritize initiatives effectively within limited resources and budget constraints
  • Serve as the primary point of contact for technology-related decisions across the business
Qualifications & Experience
  • 8+ years of experience in IT leadership, with exposure to digital transformation initiatives
  • Experience working in growth-oriented or resource-constrained environments
  • Demonstrated ability to build and execute strategy with limited resources
  • Broad technical knowledge across infrastructure, applications, cloud solutions, and cybersecurity
  • Experience managing vendors and third-party technology providers
  • Strong business acumen and ability to communicate effectively with non-technical stakeholders
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.

Job Requirements

On-Site
By using best practices and optimal employee recruiting strategies, Kavaliro provides employers with employment solutions by providing the most qualified and professional employees, who can staff both project and permanent positions in order to ensure the ongoing success of all types of businesses. We use a streamlined-yet-thorough approach to staffing that saves our clients administrative time, resources and money.
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About Orlando, FL

Explore exciting job opportunities in the vibrant city of Orlando, Florida! Known for its endless sunshine, world-famous theme parks including Walt Disney World and Universal Studios, a thriving arts scene with galleries like the Orlando Museum of Art, and a variety of recreational activities such as Lake Eola Park and the iconic Lake Eola swan boats, Orlando is a hub of innovation and creativity. With a booming economy and diverse job market, this city offers growth potential and a unique lifestyle that blends southern charm with modern amenities. Discover your next career move in Orlando and be part of a dynamic community that celebrates diversity and opportunity. Dive into our job listings today and kickstart your professional journey in the heart of the Sunshine State!

What to expect when working with Kavaliro

Just like with our clients, we build our process to meet each individual candidate s needs. Our recruiters take the time to listen to your career goals and ambitions, then work one-on-one with you to help place you in a company that provides the best professional fit.

01

Call us with a detailed overview of your experience, skills, background, and goals. If you are local and prefer, we will set up a face-to-face interview.

02

You will be asked to complete an online assessment form to assess your skill level. At the same time, your references will be checked.

03

Your Kavaliro recruiter will discuss and review potential job opportunities.

04

When you and your recruiter agree on a potential match, you ll be briefed with helpful insight into the client s needs.

05

When you begin your employment tenure with the client, Kavaliro will continue to be there to support you in your career.

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