Antonio Caballero Inadvertently Discovered HR, Now He’s Building a World-Class Organization at Transportation One

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“At the end of the day, HR is about service and helping people build careers and lives they might not have believed possible.”

Antonio Caballero has spent his career implementing systems that build businesses and help people grow. The vice president of human resources at Transportation One (T1), a fast-growing Chicago freight brokerage, Marine Corps veteran and Chilean immigrant is building a people operation designed to be as mission-critical as any revenue-generation team. While it’s his priority, he’s ensuring that mission is rooted in value creation, service, discipline, and opportunity.

When Caballero joined T1 in 2022, he stepped into an industry he did not know existed. Freight brokerage was new to him, but building a modern HR function from the ground up was not.

What he found was a business with strong entrepreneurial energy, but what he describes as a not-yet fully realized HR organization, reliant on manual processes and antiquated technology. Accordingly, he moved quickly to address departmental inefficiencies, while starting to build a highly strategic HR function.

Over the past several years, Caballero has methodically put in place what he considers the pillars of a world‑class HR organization: a dedicated talent acquisition engine aligned to aggressive growth goals, a modern HRIS to manage a growing workforce, a structured employee relations program, and a deeper focus on employee training, and leadership development.

Technology, for Caballero, is only useful if it translates into better experiences for employees and adds value. With T1’s new platform, he and his team have embedded regular pulse surveys and feedback loops so the business can continuously track employee morale, sentiment, and test whether new programs meet employee’s needs. He also formalized a company‑wide cadence of one‑on‑one conversations, requiring supervisors to sit down with employees at least twice a year in a structured way that emphasizes personal connection as much as performance.

Vendor relationships have also been foundational in Caballero’s success at T1. For instance, his growing reliance and collaboration with BHS Insurance’s Chief Growth Officer, Spencer Olson, has been critical in identifying market trends which keep T1’s benefit scheme highly competitive and supports the company’s retention strategy.

Caballero traces his leadership approach back to a formative journey that began long before logistics, his childhood immigration from Chile to Long Island and his decision, in a working‑class household with limited options, to enlist in the U.S. Marine Corps. Immersed in a new language and culture as a child, he learned to adapt quickly. As a young Marine, he learned something more enduring: the responsibility to take care of the people around you.

The VP talks about the Marine Corps as a perfect arena for leadership development, one that instills deceptively simple principles he sees lacking in corporate life, like ensuring your people have what they need to succeed, addressing problems with clarity, and understanding that leaders exist to serve.

That desire to serve serves as the leader’s foundation, whether that means advocating for employees, supporting owners and peer executives, or designing programs that create a positive and economically rewarding experience for stakeholders.

Caballero’s path into HR was anything but set in stone. “I didn’t plan any of this. I just kept looking for ways to grind, learn, and support my family, and that path led me into HR,” the executive says.

After four years stationed mostly in Quantico, he transitioned out of the Marines, took drafting courses at night, and eventually worked in design engineering in Chicago for about six years while earning his management degree from DePaul. The 2001 recession cost him his engineering job, pushing him into a period of odd jobs, insurance sales, and hustling to support a young family and a mortgage.

A chance application at a Home Depot kiosk changed everything. Initially hired for his electrical design background, he moved into an HR role just three months later at a substantial pay cut compared to engineering, but with a sense that he had finally aligned his education and career ambition. That moment, he says, is when he knew instinctively that his trajectory would take off, and it set him on a path through progressively larger HR roles in myriad industries.  

The executive states, “I have been extremely fortunate that I’ve had an opportunity to work for world-class organizations such as The Home Depot, John Crane and others, where I learned the science and art of people management. He adds further, “these leading companies supported my personal development ambitions including pursuing an MBA and obtaining advanced credentials through Harvard Business School and Cornell ILR – a hallmark of great companies”. 

Caballero is equally grateful that he’s had leaders that mentored him and provided a vision of what an HR career could provide both professionally and personally. Such a mentor was Don Koop, Americas VP at John Crane, who Caballero emulates in his day-to-day work.

At T1, Caballero’s service mindset also translates into a deliberate focus on equity and access. One of his early initiatives was introducing a more intentional DEI program to attract and retain people of color and other underrepresented groups into an industry that has not always reflected the diversity of the communities it serves. He views HR as a lever for social mobility, particularly for those who, like him, may not have grown up with obvious pathways into corporate careers. T1’s President, Pat Gillihan is highly supportive of this initiative as it reflects the company’s position that diversity is a driver of ideas and consequently of business growth and competitiveness.

Despite his senior title, Caballero speaks with the urgency of someone who feels far from finished. He is a strong advocate for personal development, tackling books on leadership, biographies, and business, again emulating personal development behaviors of highly effective and inspirational leaders such as Lincoln, Roosevelt, and Churchill. He feels most engaged when finding that essential flow state both in his HR work and in his personal life, maintaining routines around fitness, self‑care, and ongoing learning that reflect the same discipline the Marines instilled, refined for the civilian world.

“My happiest moments at work are when I’m in that flow state, fully immersed in solving T1’s complex HR problems and helping the business and its employees move forward,” Caballero says.

He is also reconnecting with his military roots through the Marine Corps League, supporting Marine veterans, many of whom carry the invisible scars of combat, through advocacy and community. For Caballero, this renewed engagement is another expression of the same principle that guides his HR leadership, those who are fortunate have a responsibility to serve those facing steeper climbs.

“The more people you serve, the more impact you can have, and the more opportunities you create for yourself and others. This is the secret to success in career and life,” he says.

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