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Ridley Jacobs
Ridley Jacobs

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From Flint to the Boardroom: How Jay Roland Turned Dice Rolls into Decision-Making Power

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Born and raised in Flint, Michigan, before the water crisis, Jay Roland never struggled to access clean water. But growing up in Flint still came with its own set of challenges—he remembers standing in lines for milk and government cheese and learning early on the value of resilience.
While many around him chased trouble, Jay chased dragons—the kind you find in Dungeons & Dragons campaigns and rare cards in Magic: The Gathering booster packs. What some might have dismissed as nerdy pastimes, Jay recognized as early training grounds: mastering strategy, leadership, and foresight. These weren’t just hobbies—they were foundational skills that would later define his approach to life and leadership.
Jay’s entry into tech began in 1999, when he stepped into the IT world with a hunger to learn. By 2010, his passion aligned with purpose—he was sent into hospitals to modernize outdated systems, replacing pen-and-paper processes with electronic patient records. It wasn’t glamorous work, but it was deeply meaningful. Jay knew he wasn’t just installing software—he was helping caregivers provide better treatment.
In time, he joined syncreon, where he evolved from simply managing incidents to redesigning how systems functioned. He automated processes, reduced ticket resolution times, and created smarter workflows. But when syncreon asked him to juggle three roles without additional compensation, Jay made a bold move: he walked away, standing firm in his belief that value should be met with respect.
Around this time, Jay and his family faced one of their most devastating challenges. A flood destroyed their home, wiped out their possessions, and ruined his cherished sword collection. With no insurance compensation, they had to start from scratch. And they did.
Jay and his family moved to Tennessee during his transition to Syntel (later acquired by Atos), where he would break down silos, rise to Director, and oversee service delivery for hundreds of employees. The experience honed his leadership even further.
His next chapter brought him to Ally Financial, where he was entrusted with managing global incident response and shaping IT policies. He then took on the challenge of building ServiceNow systems from the ground up at Wellpath, supporting over 20,000 healthcare professionals nationwide.
Today, Jay serves as a Director for one of the top 50 largest healthcare systems in the United States. His role isn’t just about systems and strategy—it’s about impact, integrity, and innovation.
Beyond the boardroom, Jay is a passionate martial artist and fencing instructor. He creates homebrew campaigns for D&D, collects swords, paints miniatures, and still finds time for weekend board game nights. He’s also a devoted husband and father to five remarkable kids who mirror his sense of humor, grit, and imagination.
In 2023, Jay unlocked another lifelong achievement: publishing his debut novel, Shadow of the Soul Blade, the first installment in the DarkThorne Chronicles—an epic fantasy saga years in the making. It was more than a creative project—it was a declaration that no matter your title or age, the story inside you deserves to be told.
Jay Roland’s story includes a broad range of personal and professional experiences—from his early days in Flint to executive leadership in healthcare technology. His trajectory reflects adaptability, strategic thinking, and sustained commitment to both his craft and his values.

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