Nick DeGregorio and Maj. Gen. Alex Fink on Leading Through Transformation and Building Influence

CEO Roundtable

Maj. Gen. Alex Fink’s career is a remarkable blend of military discipline and corporate strategy, offering insights few can match. As Chief of Army Enterprise Marketing in Chicago, he oversaw one of the Army’s most transformative initiatives—the “Be All You Can Be” campaign—while guiding a team to build the Army’s marketing capabilities into a modern, data-informed powerhouse. But his journey began far from Chicago, on a working farm in rural Missouri, where values like hard work and resilience were instilled early.

Maj. Gen. Fink attended the University of Missouri, where he joined the ROTC, an experience that sparked his lifelong dedication to service. Over a distinguished military career that spans more than three decades, he’s held numerous high-stakes commands, from leading multinational units in Iraq and Afghanistan to overseeing vital logistical operations across the globe. This breadth of experience not only underscores his leadership but also shapes his approach to culture-building in organizations.

For Alex, authentic leadership is essential. He emphasizes that leadership isn’t about mimicking others; it’s about being yourself and standing by the principles you believe in. “You can’t lead if you’re constantly trying to be someone else,” he explains. This idea—of authenticity as the cornerstone of effective leadership—has guided him throughout his military career and into his current role, where he helps mold the Army’s public image and outreach efforts.

A Major General’s approach to leadership goes beyond strategies; it’s grounded in practical actions. Known for his accessibility, Alex breaks the mold of many corporate leaders by actively seeking out “collisions”—unplanned interactions that reveal valuable insights. “I seek out those small collisions,” he says, knowing that real connections with his team build trust and foster a culture where everyone feels valued. This open-door policy, uncommon in both the military and corporate worlds, has made him an accessible leader who values transparency and collaboration.

One of Alex’s core principles is what he calls “don’t walk past a mistake.” He believes that leaders must address issues head-on and avoid letting small missteps fester. This mentality of accountability is not only vital internally but also essential for fostering relationships with external partners, who are crucial in driving an organization’s mission forward.

Collaboration, both inside and outside the organization, is another key to Alex’s leadership style. He’s quick to acknowledge that large-scale change requires allies, and he sees partnerships as essential, whether it’s with peers, other divisions, or external organizations. “If you're driving cultural change, you need partners on board,” he says. This collaborative mindset was pivotal during his time in military commands and continues to be a cornerstone of his corporate leadership.

As the architect of the Army’s “Be All You Can Be” campaign, Alex had to make difficult decisions. With a limited budget, he prioritized investments in data and technology, even at the expense of reducing media visibility temporarily. “It was a risk,” he admits, but one that ultimately allowed his team to create a more precise, targeted approach to marketing. This decision reflects his understanding that short-term sacrifices are sometimes necessary to achieve long-term success, an insight he draws from both military and corporate environments.

The Major General’s military background has taught him invaluable lessons about resilience and perspective. He’s led through the high stakes of combat, an experience that has trained him to keep things in perspective and stay grounded under pressure. “In a year from now, is anyone going to remember? And if they do, will they care?” he asks himself. This mentality has become a compass in his career, helping him make decisions without letting minor setbacks derail his focus.

Alex’s leadership is also rooted in compassion. He sees his team as more than just colleagues; he understands that personal and professional lives are intertwined. “People don’t bifurcate between personal and professional lives,” he shares. By taking time to understand what’s going on in his team members’ lives, he fosters an environment of support and loyalty. His approach to leadership is holistic, aiming to create an environment where people are empowered to succeed and feel part of a mission that matters.

Maj. Gen. Alex Fink’s journey has been shaped by resilience, collaboration, and an unwavering commitment to authenticity. His story offers insights for anyone seeking to lead with purpose and build a culture of influence, whether on the battlefield or in the boardroom.