Chief Information Officer, Transformation and Technology Services
Year Up United
• www.linkedin.com/school/year-up-united
• Full-time
Jan 2023 - Present
Tampa, Florida, United States
Chief Information Officer
Year Up United
• www.linkedin.com/school/year-up-united
• Full-time
Jan 2021 - Dec 2023
Boston, Massachusetts, United States
Founder and vChief Information Officer
Solutionist Ventures
• www.linkedin.com/company/solutionistventures
• Contract
Jan 2017 - Dec 2021
Tampa, Florida, United States

4x CIO | Orbie Winner | Ed Tech | AI Workforce & Human Capital Strategist | Digital Transformation & Operational Excellence | National - Global Leadership | Non Profit - Private Equity Experience | CIO+, Year Up United
As CIO of Transformation and Technology Services at Year Up United, Gary is at the forefront of revolutionizing how young adults access career opportunities through digital innovation. A visionary leader who speaks nationally to CIOs, technology leaders, and aspiring professionals, he champions the transformative power of technology in reshaping workforce development and educational access. With over 30 years of experience, Gary leads Year Up United's enterprise-wide digital transformation, orchestrating a strategic shift from project-based operations to a product-focused organization while harnessing emerging technologies like AI to revolutionize essential skills training. He oversees transformation and technology services across business intelligence, product and design, learning excellence, and business operational excellence. His expertise in executive leadership, digital roadmap creation, and customer-centric solution delivery has earned him the 2023 Florida CIO Corporate ORBIE Award, recognition as a 2024 National ORBIE Finalist, and being named one of the 30 most influential business leaders in tech in 2022. Gary serves as board member and workforce committee chair at Gulf Coast JFCS, and as finance committee chair and Treasurer at St Pete Free Clinic. Through speaking engagements nationwide and investments in education and STEM initiatives, he inspires the next generation while promoting technological innovation as a catalyst for social change. His mission remains clear: leveraging expertise and influence to create pathways of opportunity and drive meaningful impact in communities worldwide.
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dxc.technology
yearup.org
Tampa, Florida, United States