Cunningham said he first fell in love with tech in college when he was studying business and accounting. “It was like stepping into a world where innovation was the norm, and it really sparked my curiosity. The excitement of being part of something that was constantly reshaping business and redefining possibilities made me switch to tech. I've been passionate about it ever since.” 

The longtime IT pro’s career path has taken him through both the banking and insurance sectors, but Cunningham said there was an early, unconventional experience that prepared him for his journey.

“One of the early formative experiences in my life happened when I was just ten years old,” he said. “My brother, who was eleven, and I spent an entire summer in rural Ireland, working on a small family farm. This experience was a world apart from our upbringing in Cleveland, Ohio. The stark contrast between our urban life and the demands of farm work taught me invaluable lessons in adaptability, resilience, and the importance of curiosity. Navigating the challenges of that summer—learning new skills, adapting to unfamiliar routines, and embracing a completely different way of life—shaped my ability to thrive in diverse and evolving environments. These qualities have been instrumental in my journey to becoming the CIO at Grange, where the ability to adapt and innovate is key to success.”

Adaptation in Adversity

That ability to adapt helps Cunningham navigate difficult experiences in his career, turning “fails” into opportunities.

“During my career, I've had my fair share of failures, but one that stands out was during a critical customer conversion weekend at an acquired bank. I was responsible for upgrading the infrastructure at all the bank’s branches—a complex operation under tight deadlines. However, we encountered significant delays with a subset of branches, which took far longer to convert than anticipated,” Cunningham remembered. “This experience was a pivotal learning moment. It forced us to step back and reevaluate our approach. We realized that trying to execute both the physical hardware upgrades and the software changes, simultaneously, was a recipe for delays and unnecessary complications. By decomposing the process and staggering these tasks, we were able to streamline future conversions…[it] taught me the value of agility and continuous improvement, reinforcing that setbacks often lead to breakthroughs when approached with the right mindset.”

The Power of Collaboration

The IT Martini Today pre-party charity partner is the CIO Tomorrow student scholarship program. Cunningham said he chose the program to be the charity partner because tech skills are not enough to create a collaborative, thriving tech community, or Silicon Heartland, as he has called it.

“We need a workforce that is both influential within their organizations and deeply connected to the community. The scholarships offered through CIO Tomorrow are more than just financial awards—they’re gateways to mentorship, networking, and real-world experiences that set these students apart,” Cunningham said. “Recipients have the unique opportunity to engage directly with technology leaders and other highly motivated peers, giving them a head start not just in their careers but in becoming future leaders. Supporting this program means investing in the next generation of innovators who will drive our region’s success.”

When asked what advice he’d give to future IT leaders and tech pros given the ever shifting nature of the field, Cunningham leaned on education, in all its forms. 

“...one thing we can count on is the accelerating pace of change driven by emerging innovations. To navigate this ever-evolving landscape, my advice to future CIOs and tech leaders is to stay deeply engaged and committed to continuous learning,” Cunningham said. “Be proactive in seeking out new knowledge, and don’t underestimate the power of collaboration. Building strong networks and fostering a culture of teamwork will be crucial in adapting to the shifts ahead. Ultimately, those who are curious, adaptable, and collaborative will be best positioned to lead in the face of constant change.”

Cunningham pointed to the variety of learning opportunities available to all attendees at the CIO Tomorrow conference. 

“I’m particularly excited about the keynotes and breakout sessions. These sessions promise to be incredibly informative and thought-provoking, offering a deep dive into the latest trends, challenges, and innovations. It’s an invaluable opportunity to gain fresh perspectives and actionable insights from some of the brightest minds in the field. But beyond that, I’m eager to connect with fellow leaders and peers, exchanging ideas and experiences that will help shape the future of our organizations and the broader community. The energy and exchange of knowledge at this conference is always a highlight for me.”

It’s no surprise that the advice Cunningham gives to emerging IT leaders is in line with his advice to all tech pros and leaders attending the CIO Tomorrow conference. 

“To truly make the most of your CIO Tomorrow experience, I recommend clearing your calendar for the entire day and fully immersing yourself in the conference,” he said. “Attend as many sessions as possible—each one is a chance to gain valuable insights and discover new ideas that can drive innovation in your organization. Beyond the sessions, take full advantage of the networking opportunities. Engage with leaders and peers, share your experiences, and listen to theirs. These connections often lead to collaborations and partnerships that extend well beyond the conference. The more you invest in the experience, the more you’ll gain from it.”