BlogSeptember 18, 20264 min read

Why Wipfli's new CTO starts every technology conversation with people

Wipfli Insights Team

When John Rosenbaum talks about technology, he doesn’t start with AI. He doesn’t start with platforms, systems or digital transformation. He starts with people.

That may seem unusual for a chief technology officer. But for Rosenbaum, Wipfli’s new technology chief, his focus has always been about helping people do better work, make better decisions and create better outcomes. It’s a perspective that shapes how he leads, how he approaches innovation and why he was drawn to Wipfli in the first place.

Technology only matters if people can use it

Organizations today are navigating an unprecedented pace of technological change. Artificial intelligence, data and digital tools continue to reshape how businesses operate. Rosenbaum believes the challenge isn’t finding new technology. It’s making sure technology creates meaningful value.

“My focus and goal is to use technology to power our strategies,” he said. “My goal for the technology organization is to become a trusted partner, both to our external clients and our associates.”

Whether the conversation is about AI adoption, data products or digital transformation, Rosenbaum focuses on helping people understand how technology connects to their work and how it can help them succeed. In his view, even the most innovative solution falls short if people don’t know it exists, how to use it or why it matters.

A leadership philosophy shaped by service

While Rosenbaum has a strong track record of leading technology organizations through growth and transformation, he doesn’t define himself primarily by his professional accomplishments. In fact, his LinkedIn headline begins with two roles that matter most to him: husband and father.

“These are my priorities,” he said. “Husband first, father second.” It’s a simple statement, but it offers insight into the type of leader he strives to be.

Rosenbaum describes himself as mission-driven. He believes leadership is ultimately about serving people, helping them grow and leaving them better than he found them. That philosophy influences how he approaches technology at Wipfli.

Technology investments are important, but people remain at the center of every decision. Success is measured not only by what’s built, but by whether associates and clients are empowered to move forward with greater confidence and clarity.

Building trust in times of change

Trust is another principle that guides Rosenbaum’s leadership. He believes strong teams are built on vulnerability-based trust, where people feel comfortable asking for help, sharing concerns and acknowledging when they don’t have all the answers.

That approach becomes especially valuable during periods of transformation, when organizations are learning, adapting and experimenting with new ways of working. Rather than focusing on who’s responsible for a problem, Rosenbaum encourages teams to focus on what’s next.

That mindset helps create an environment where innovation and accountability can coexist. People can learn, challenge assumptions and improve together without fear of making mistakes.

Investing in the next generation

Outside of work, Rosenbaum’s commitment to developing people extends well beyond the workplace. He mentors a group of boys through his church, helping them build leadership skills and navigate life’s challenges. He also serves as an industry mentor for engineering students at Southern Methodist University, supporting emerging leaders as they prepare to enter the profession. Whether working with college students and other young people or technology teams, Rosenbaum believes leadership is ultimately about helping others realize their potential.

The experience reflects something deeper than just a volunteer commitment. It reflects a belief that growth happens when people are supported and encouraged to reach their potential. He brings this principle into his professional life as well. Whether helping associates adopt new technology, guiding teams through change or exploring the possibilities of AI, Rosenbaum sees leadership as an opportunity to help others succeed.

Looking ahead

Rosenbaum sees himself as a leader who values focus and prioritization. He believes organizations move faster when they identify what matters most and execute with intention.

As Wipfli continues investing in data, AI and other technologies, that philosophy will help shape the firm’s approach to innovation. But beneath every strategy and initiative is something more personal: a belief that technology is most powerful when it serves people. That’s why Rosenbaum starts every technology conversation the same way: not with systems or tools, but with people.