Robert Rosales – Oak Harbor Freight

Oak Harbor Freight Lines is a regional freight carrier with roots dating back to 1916. Based in Auburn, Washington, the company serves the western United States, delivering less-than-truckload freight with precision and reliability. As a cornerstone of its operations, Oak Harbor emphasizes the efficiency of its logistical network and the role of technology in keeping its services ahead of the curve.

Robert Rosales | Oak Harbor Freight | Vice President, Information Technology

At the helm of this technological evolution is Robert Rosales, vice president of information technology, whose 30-year career in IT has uniquely prepared him to navigate the delicate balance between innovation and operational pragmatism.

Rosales’s journey into the tech world wasn’t straightforward. Initially inspired by architecture and Frank Lloyd Wright’s works, he envisioned designing skyscrapers. However, a chance conversation with a friend redirected his focus to computers, a field still in its infancy at the time. This pivot led Rosales to a master’s degree in information management from the University of Washington and a series of roles that honed his expertise, including stints at Universal Studios Hollywood, Nintendo and Starbucks.

Rosales first joined Oak Harbor as an IT manager early in his career but left to pursue other opportunities. When he returned as IT director in 2012, the company’s technological landscape—and his role within it—had evolved significantly. Now serving as vice president since February 2023, Rosales oversees a growing IT department, which has expanded from nine to 18 team members under his leadership. While most of the team operates out of Auburn, a few are based in Texas, reflecting the increasing flexibility of a hybrid work environment.

Rosales quickly acknowledges the challenges of scaling a department and integrating new technologies within a company steeped in tradition.

“When you grow a team to double its size, the dynamics shift,” he explains. “We’ve had to adopt more structured policies and procedures, especially with hybrid work. What used to be solved with a quick chat over a cubicle now requires formalized guidelines.”

Embracing change

Rosales’s approach centers on balancing technological ambition and business readiness. Oak Harbor is not a company that rushes to adopt the latest technology for the sake of novelty.

“There are companies that want to be at the bleeding edge, but that often comes with a lot of blood,” Rosales quips. “Instead, Oak Harbor prioritizes proven technologies that align with its operational goals and appetite for change.”

This measured approach is rooted in Rosales’s understanding that technology adoption is as much about people as it is about systems.

“It’s not just about whether the technology works—it’s about whether the company is ready to embrace it,” he says. The readiness of employees, from drivers to operational managers, plays a critical role in the success of any tech rollout. “Do you embrace change? Yes. Do you want to change? That’s a different question,” Rosales explains.

To address resistance, Rosales focuses on framing change as alleviating pain points. He likens the process to upgrading an old smartphone: If your phone constantly runs out of battery and frustrates you, upgrading becomes less about change and more about solving a problem. This pragmatic perspective helps ease the transition, even when new technology introduces temporary challenges, such as resetting two-factor authentication or learning a new interface.

One of Rosales’s key responsibilities is managing the company’s technical debt—the accumulated costs and inefficiencies of delaying necessary updates. The longer a system is left untouched, the more complex and costly it becomes to modernize.

“You end up covering inefficiencies with workarounds, and it becomes a bigger leap to adopt new technology,” Rosales warns.

He parallels industries like air traffic control, where outdated systems become so entrenched that modernization seems insurmountable.

Understanding complexities

At Oak Harbor, this means tackling both front-facing and back-end systems. User-facing applications, such as those used by drivers, often require more frequent updates to remain compatible with evolving hardware and browsers. Meanwhile, back-office systems that handle complex data processing must balance reliability and modernization. The stakes are high; cybersecurity concerns loom large, and maintaining secure, functional systems is paramount for a company handling vast amounts of data.

The challenge extends to bridging the gap between different perspectives within the organization. For example, drivers prioritize ease of use and functionality, while management may focus on operational oversight. This can create tension when implementing new tools, such as applications that comply with Department of Transportation regulations or dash cameras that provide visibility during accidents. Rosales notes generational differences in how these technologies are received: younger drivers are generally more accepting of constant recording, while older employees may be more apprehensive.

Rosales’s ability to navigate these complexities stems from his deep understanding of the human element in technology. Over the years, he has learned that successful IT leadership is about more than technical expertise.

“It’s the people that make the system work,” he says. “Without them, the system breaks down.”

This philosophy drives his team building and project management approach, in which collaboration and camaraderie are as crucial as the final deliverables.  This philosophy also drives his passion for IT coaching, mentoring, and cultural change to foster impactful and long-lasting positive change.

As Oak Harbor continues its digital transformation into 2025 and beyond, Rosales is focused on modernizing legacy systems, enhancing cybersecurity, and introducing new capabilities like artificial intelligence. However, perhaps his most enduring contribution will be the culture he has fostered within the IT department—a culture that embraces change not as a disruption but as an opportunity for growth.

In many ways, Rosales’s career reflects the evolution of technology itself. From his early days developing applications to his current role shaping IT strategy, he has witnessed firsthand how systems can drive business innovation. Yet, he remains grounded in the realization that technology is ultimately a tool that must align with the people and processes it is designed to support.

“That alignment is key to navigating the road ahead for our company,” Rosales says.

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