Luis Cruz is a Chicago-born technology leader, operational strategist, and founder of Upgrade Technology Group, where he helps organizations modernize through automation, AI, and smarter processes.
With two decades of experience spanning engineering, project management, enterprise SaaS, and cross-functional leadership, Luis bridges technical depth with business insight. He’s known for transforming chaos into structure, designing systems that make teams faster, data smarter, and clients happier.
Luis began his career at Motorola, where he helped engineer the EMX-2500 Switch before joining the Mobile Devices division to lead software integration for the launch of the iconic Motorola RAZR phone, one of the most successful mobile devices of its time. He went on to manage the software platform for the RAZR phone.
He later joined On Point Technology, the nation’s leading unemployment-insurance integrity software firm, where he rose from Senior Project Manager to Director of Operations. There, he oversaw Customer Support, Software Implementations, Marketing, Human Resources, and the PMO, driving the company’s shift from legacy on-premise systems to a modern SaaS platform. The operational frameworks, dashboards, and culture of accountability he built continue to guide the company today.
An hour with Luis feels like a masterclass in systems thinking, the kind of high-impact consultation most executives would gladly pay four figures for.
A proud Chicagoan from the Little Village neighborhood, Luis believes that true leadership is measured not only by what you build, but by who you lift along the way. He has served on numerous nonprofit boards, including the St. Jude Hispanic Advisory Board, Boys & Girls Clubs of Chicago, ALPFA Chicago, and Archer Manor Baseball.
He was a founding member and former National President of Omega Delta National Fraternity and a founding member and former Co-Chair of the University of Illinois Latino Alumni Association, helping expand both organizations’ reach and community impact.
Luis also founded and led the creation of ChicagoToyDrive.org, which for more than a decade delivered thousands of toys annually to underserved communities, and he is the founder and visionary behind Ctrl Shift Project, a nonprofit focused on teaching technology and leadership skills to inner-city youth.
