Bridging Innovation and Leadership in Digital Transformation: A Conversation with Derrick Cash
“The role of leadership is to transform obstacles into opportunities, to empower people through vision, and to drive innovation in ways that create meaningful impact.” – John C. Maxwell
In today’s fast-paced digital economy, leadership and innovation are no longer separate disciplines—they are two sides of the same coin. The ability to navigate complex transformations, implement cutting-edge technology, and empower teams to drive change is what separates thriving enterprises from those left behind.
Enter Derrick Cash, a pragmatic, data-driven, and visionary leader. As Vice President of Innovation and Delivery at RADcube, Derrick has dedicated his career to bridging technology and leadership—aligning AI, digital transformation, and enterprise IT strategies to create real-world impact.
His journey—from aligning his passion for sustainable design and applied sciences during his undergraduate studies at Indiana University’s School of Informatics, to facilitating the development of critical infrastructure projects like the City of Westfield’s Grand Park, municipal Fire Stations, a Public Safety Training Center, and a flagship mental health hospital for Indiana’s psychiatric hospital system—to leading enterprise-wide digital innovations in both public and private sectors—demonstrates the power of resilience, strategic decision-making, and a growth mindset.
But as Derrick will tell you, no leader succeeds alone. With the unwavering support of family, friends, mentors, and a belief in divine intervention, he transformed obstacles into opportunities, proving that true leadership is about persistence, curiosity, and an unyielding commitment to progress.
From Poverty and Little Access to Computing Resources to One of Indiana's Top Technology Leaders: Passion and Perseverance Over Privilege
Unlike many in the tech industry who grew up with privilege and early access to technology, Derrick’s early life reflected a different reality—one familiar to many underprivileged communities across rural America.
Raised in poverty and without access to computers, Derrick’s childhood revolved around nurturing friendships, playing sports, and embracing the mentorship and discipline that come with athletics. He spent his time exploring nature, drawing connections between seemingly unrelated sciences—biology, astronomy, physics, mathematics—and later realizing that technology is simply the application of science to solve problems.
“My circumstances didn’t define my trajectory; rather, they helped me realize that I would just have to work a little harder than some to achieve my objectives. I spent my pre-teens through high school in a rural area, with limited economic means both at home and in the community, and without access to a computer. But that afforded me the opportunity to experience the parallels and interconnectedness between the sciences.”
His father left home when Derrick was just eight years old, leaving him to take on responsibilities well beyond his years. Serving as an anchor for his family, Derrick learned the importance of discipline, responsibility, and perseverance—lessons that would serve him well in his future leadership roles.
Despite these challenges, he never saw himself as a victim of his circumstances. Instead, he used them as fuel to drive his ambition—a mindset that would eventually lead him to Indiana University Bloomington and a career in technology leadership.
A Different Path: From Military Aspirations to Technology Leadership
Originally, Derrick planned to pursue a military career. However, his path changed due to a life-saving open-heart surgery he underwent at the age of five.
Despite being in peak physical condition with no complications from the surgery, he was initially denied military admission. Undeterred, he continued applying while holding down multiple jobs after high school, eventually receiving approval to join.
But life had other plans.
During the year between high school and college, Derrick met and fell in love with his now-wife, Shana. Together, they made the decision to pursue higher education—a choice that would shape the rest of his career.
“At first, I thought to myself, ‘There’s no way I can go to Indiana University—I’m not always the best student, and I wasn’t sure I could keep up.’ But my wife, the godsend that she is, encouraged and supported me, and I took the leap. I am very fortunate to have an incredible support system among family and friends.”
With Shana’s unwavering belief in his potential, and the encouragement of his family and mentors, Derrick took a leap of faith—one that would ultimately lead to a distinguished career in digital transformation and innovation.
Discovering a Passion for Technology: A Journey from Nursing to Informatics
Initially, Derrick enrolled at Indiana University to pursue a career in nursing. As part of his coursework, he took an Introduction to Computing class—learning the basics of Windows navigation, Microsoft Office, and fundamental digital tools.
“It was just a simple course, but it sparked something inside me,” Derrick recalls.
He quickly realized that technology wasn’t just about software and hardware—it was about empowerment. The ability to help people by applying scientific principles to solve problems fascinated him.
What started as a basic computing courseignited a passion for data, analytics, and problem-solving. Derrick immediately switched his major to Informatics, with a Computer Science cognate and an Information Technology minor.
His natural curiosity, resilience, and ability to draw connections between disciplines made him stand out. He not only excelled academically but graduated:
Among the top in his class
With a 4.0 GPA in his major
And an overall 3.89 GPA
“Technology made sense to me; it came easy. I understood the language, the logic, and most importantly, the real-world applications. I was able to further strengthen my natural ability to draw parallels between the sciences, and now I had this amazing set of tools to help others do the same!”
This marked the beginning of a career that would blend data-driven decision-making, leadership, and digital transformation into one cohesive mission.
The Intersection of Leadership & Technology: From Strategy to Execution
While excelling in technical roles, Derrick realized that his true calling wasn’t just in writing code—it was in connecting people with technology to drive real-world impact.
“I didn’t want to just code or produce algorithms all day . I needed human interaction, the ability to leverage my people skills, and to create solutions that make life better. I wanted to offer the world my best—and for me, that meant integrating technology with leadership.”.
This realization led Derrick to pursue an MBA from Indiana Wesleyan University, a decision that set the foundation for his leadership trajectory.
Just one month after earning his MBA, Derrick’s career took off like a rocket:
Director of Informatics – City of Westfield
• Lead the City’s Project Management Office, Technology Support, and Geographic Information Systems teams.
• Spearheaded urban planning technology integration, including the City’s flagship Grand Park sports complex.
• Redesigned the city’s primary and backup data centers and built a new fire station.
• Helped technically connect and support a public safety training facility.
Senior Manager of Enterprise Architecture → Deputy CTO – State of Indiana
• Led state-wide IT modernization efforts, enhancing digital government services.
• Established governance frameworks for statewide digital initiatives
• Managed enterprise-level infrastructure, cybersecurity, and cloud adoption.
• DroveAI and data analytics frameworks for state departments.
• Oversaw strategic planning for digital transformation initiatives.
His role at the State of Indiana was particularly impactful, as he worked across multiple agencies to modernize operations, implement AI-driven analytics, and enhance IT governance frameworks.
“Government IT is often perceived as slow-moving, but we proved that with the right strategy, leadership, and execution, we could implement transformational change at scale,” Derrick shares.
Now, as VP of Innovation & Delivery at RADcube, Derrick manages multi-national teams across the U.S. and India, ensuring that organizations can harness the power of digital transformation, AI, and technology strategy to remain competitive and innovative.
RADcube is a forward-thinking technology consulting and solutions firm specializing in digital transformation, data engineering, cloud modernization, AI-driven innovation, and cybersecurity. With a strong foundation in both public and private sectors, RADcube delivers end-to-end solutions that empower organizations to operate more efficiently, securely, and intelligently. With expertise that spans cloud platforms like Azure and AWS, data platforms such as Databricks, and advanced AI/ML integrations tailored to business and government needs. As trusted partners to leading institutions like Eli Lilly, the State of Indiana, and Citizen’s Energy Group, RADcube consistently demonstratesthe ability to solve complex problems, drive innovation, and deliver measurable impact. Whether implementing statewide Learning Management Systems, modernizing legacy permitting tools, or leading public health AI initiatives through it’sVersante product, RADcube continues to serve as a leader in designing practical, scalable solutions that shape the future.
The Role of AI in Leadership & Decision-Making
Derrick is an outspoken advocate for the responsible use of AI in leadership and decision-making.
“AI is already shaping the way businesses operate, and in the next five years, it will become even more integral to leadership strategies,” he explains.
Key areas where AI is transforming leadership:.
Predictive Analytics: AI is enabling leaders to anticipate market trends and customer behaviors, making proactive decision-making possible.
Automation of Routine Decisions: AI is handling repetitive decision-making tasks, freeing leaders to focus on high-impact strategies.
Human-AI Collaboration: AI enhances leadership capabilities, but human judgment remains essential to balance ethics and contextual understanding.
However, Derrick also cautions against blind reliance on AI:
“AI is powerful, but it must be developed and used responsibly. Right now, we need humans in the loop to validate AI-driven insights. The future will bring more automation, but continued ethical oversight is crucial.”
Derrick believes that AI should not replace human leadership, but instead augment it—providing data-driven insights while allowing leaders to focus on creativity, strategy, and people management.
To deepen his expertise, Derrick recently completed the MIT CSAIL course on Artificial Intelligence: Implications for Business Strategy, further solidifying his role as a leader in AI-driven digital transformation.
Why Digital Transformation Needs a Leader’s Blueprint
Digital transformation isn’t just about adopting new technology—it’s about fundamentally changing how an organization operates, delivers value, and competes in a digital-first world.
According to Derrick, successful digital transformation requires:
A Clear Vision: Leaders must anticipate future trends and align technology with business goals.
Agility & Adaptability: Change is constant, and leaders must pivot when necessary to maintain relevance.
Empathy & Inclusivity: The biggest challenge in digital transformation isn’t technology—it’s getting people to embrace change.
Data-Driven Decision-Making: Reliable data, not just instincts, should drive strategic choices.
“Digital transformation is not just a technology shift; it’s an organizational mindset shift,” Derrick emphasizes.
He also points out that many companies fail at digital transformation because they focus solely on technology, neglecting people and processes.
4 Leadership Principles for Digital Transformation
Derrick emphasizes that strong leadership is the true driver of digital transformation. His 4 key leadership principles:
Visionary Thinking → Seeing beyond immediate challenges to shape a long-term strategy.
Adaptability & Resilience → Flexibility and responsiveness in an ever-evolving tech landscape.
Empathy & Inclusivity → Understanding the human impact of tech adoption and change.
Data-Driven Decisions → Using reliable analytics, not just instincts, to guide transformation.
To deepen his expertise, Derrick recently completed the MIT CSAIL course on Artificial Intelligence: Implications for Business Strategy, further solidifying his role as a leader in AI-driven digital transformation.
“Leadership is certainly not about making unrealistic demands on a team in the name of the almighty dollar—it’s about creating and sustaining a culture where all stakeholders feel valued and empowered to influence change in their fields of expertise, always with the vision in mind,” Derrick says.
Will Leadership Survive the Next Wave of Disruption?
Looking ahead, Derrick remains committed to mentoring the next generation of tech leaders and driving innovation through a foundation of ethics, collaboration, and lifelong learning.
His advice for future leaders?
“Find your passion, stay motivated, expand your network, and never stop learning. That’s what will drive you forward.”
Derrick’s story is a testament to resilience, continuous learning, and the power of a people-first leadership approach—principles that define the future of digital transformation and innovation.
Conclusion
As businesses worldwide undergo rapid digital transformation, leaders like Derrick Cash set the standard for strategic innovation, ethical AI adoption, and people-centered leadership. His journey—from overcoming barriers to becoming a digital transformation leader—demonstrates the importance of resilience, vision, and adaptability in today’s digital-first world.
What’s next for digital transformation? Share your thoughts in the comments!
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Editor Bio
I’m Isha Taneja, serving as the Editor-in-Chief at "The Executive Outlook." Here, I interview industry leaders to share their personal opinions and provide valuable insights to the industry. Additionally, I am the CEO of Complere Infosystem, where I work with data to help businesses make smart decisions. Based in India, I leverage the latest technology to transform complex data into simple and actionable insights, ensuring companies utilize their data effectively.
In my free time, I enjoy writing blog posts to share my knowledge, aiming to make complex topics easy to understand for everyone.
