CEO MONTHLY / CEO OF THE YEAR 2024 11 CEO MONTHLY / MARCH 2025 7 Jul23542 In an era where digital transformation is no longer optional, Heirloom Computing is revolutionizing how Global 2000 companies modernize their critical mainframe systems. Under Gary Crook’s visionary leadership, the company is setting new standards in cloud migration, earning him the prestigious title of Cloud Migration CEO of the Year 2024. We explore how his journey from teenage programmer to industry leader is reshaping the mainframe modernization sector. The Mainframe Legacy The story of mainframe computing is intrinsically linked to the evolution of modern business. Since IBM’s groundbreaking mainframe systems of the 1960s, these technological powerhouses have become the backbone of global commerce. Today, they process an astounding 70% of all global financial transactions and underpin two-thirds of America’s GDP, with 70% of Fortune 500 companies relying on IBM mainframes for their mission-critical operations. Yet, while these systems remain fundamental to global business operations, the application model of these critical mainframe workloads has remained essentially unchanged since the late 1960s. In a world where technological innovation accelerates exponentially, this presents both a challenge and an opportunity. Heirloom Computing: Bridging Past and Future At the intersection of legacy reliability and modern innovation stands Heirloom Computing. Heirloom was built to enable large organizations to reimagine their mainframe applications on modern stacks so they can be activated as agile assets that can accelerate the delivery of strategic business requirements for the decades to come. Heirloom is recognized by the analyst firm ISG as the multi-cloud leader for mainframe modernization software and for its unique pioneering approach to mainframe transformation. The Heirloom platform enables organizations to migrate their mainframe applications to modern platforms, reducing operational expenses by at least 60% while creating agile application environments that can rapidly adapt to changing business needs. What really sets Heirloom apart is its comprehensive understanding that modernization extends beyond technical challenges. The company’s approach encompasses technical, operational, and cultural dimensions, allowing clients to navigate their transformation journey at an optimal pace while maintaining complete control and transparency. Their proven track record of successful implementations, partnering with global system integrators like Accenture, “Transform with confidence, innovate without bounds” Capgemini, and Cognizant, stands testament to their expertise. A Journey of Innovation and Leadership Now that Heirloom is an established company, Gary Crook’s role is focused on how best to scale the business, and he recognizes that in comparison to the challenges of starting Heirloom, scaling is equally as hard. Gary’s path to becoming a transformative leader in enterprise computing began with a moment of inspiration in a school classroom. At age 13, a chance encounter with a Research Machines 380Z computer sparked a passion for coding that saw Crook spending much of his spare time over the following 5 years in his bedroom coding—a transformative time that ultimately would shape his life and career. Gary joined Micro Focus in the mid-1980s and recalls how one of the founders, Brian Reynolds, built the company on the (many would say) crazy idea of bringing the COBOL language to microcomputers (hence the company name). It took off, and consequently, there were many opportunities to learn and adapt. With the humbling realization that he was not a top-tier programmer, Gary gradually transitioned from regularly coding to leading product development teams. By the late 1990s, Gary was global vice president of Product Development, managing 450 staff across 10 geographies. The impetus for founding Heirloom Computing came from Crook’s growing frustration with the pace of innovation and inability to influence the direction CEO MONTHLY / 2024 CEO of the Year Awards 11
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