Gary Crook: Pioneering the Future of Mainframe Modernization

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.

“Transform with confidence, innovate without bounds”

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, 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 of the product roadmap. “It became a ‘put up or shut up’ scenario,” he reflects. This drive for meaningful change, combined with the departure of a much-respected CEO and a second move to California, led to the creation of a company that would fundamentally reshape mainframe modernization.

Leadership Through Trust and Empowerment

Crook’s leadership philosophy, which he describes as “steer and trust,” has been instrumental in building a high-performing, distributed team spanning multiple countries and cultures. The approach is deceptively simple: hire curious, committed, and brilliant people, make the priorities clear, and empower them to determine the most valuable work to pursue.

Gary has been keen to implement trusted leadership initiatives, and he refers to the book “Good to Great”, by Jim Collins, who refers to the most effective leaders as being “an individual who blends extreme personal humility with an intense professional will.”

“The most powerful shift in my leadership evolution was the gradual realization that you must let go,” Crook shares. “This means trusting others when you are the one being held accountable.” This philosophy has fostered a unique culture where team members work from wherever they are, at whatever time they choose, with the flexibility to take as much time off as needed.

Real Impact, Real Results

The effectiveness of this approach is evident in the number of Heirloom in-production clients worldwide today, coupled with the strong team of professionals working with Gary to ensure the success of each customer’s unique journey.

Looking ahead, Crook’s vision for Heirloom Computing centers on scaling and innovation. The rise of Generative AI marks a new era for enterprises worldwide, and Heirloom is fully embracing this transformation. Through the release of h/GENAI, Crook and the Heirloom team are bringing these AI capabilities to their solution and customers.

Gary’s advice for aspiring leaders is simple: work with great mentors, embrace personal development through coaching, adhere to your vision, and, most importantly, surround yourself with brilliant people.

Under Crook’s leadership, Heirloom Computing has emerged as a pioneer in mainframe modernization. The company’s innovative platform combines the reliability of legacy systems with cloud capabilities and AI integration through h/GENAI, enabling Global 2000 organizations to transform their mission-critical applications into agile, future-ready assets. With a proven methodology and growing portfolio of successful implementations, Heirloom is showing how legacy systems can drive innovation and create lasting business value for decades to come.