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Driving Digital Change Insights from Caleb Walker



In a recent podcast episode, I had the pleasure of speaking with Caleb Walker, CEO of Digital Insurgency. Caleb is a seasoned leader with a fascinating background that spans two decades in the Canadian Army, including three tours in Afghanistan. His last role as the Task Force Commander in Kabul earned him the CDS Commendation, highlighting his exceptional leadership and dedication. Transitioning from military service, Caleb has become a prominent figure in digital transformation, particularly in connecting disjointed communities within large organizations. This article discusses, "Driving Digital Change Insights from Caleb Walker".

From Combat to Cyber: Caleb's Journey

Caleb's journey from the battlefield to the boardroom is nothing short of inspiring. After serving 20 years in the Canadian Army, he transitioned into the tech industry, focusing on upskilling veterans and driving digital transformation within government sectors. As the Country Manager for WithYouWithMe, Caleb helped 3,000 Canadian veterans acquire cyber and technology skills, employed 130 veterans, and implemented 20 cyber solutions within the federal government. His work has not only transformed lives but also enhanced the efficiency and security of government operations.

Bridging Information Silos

One of the key topics we discussed was the challenge of connecting information silos in large organizations. Caleb emphasized the importance of seamless communication and collaboration across different departments to drive innovation and efficiency. "It's about setting up the right conversations," Caleb explained. By identifying and connecting key stakeholders, organizations can break down barriers and foster a culture of collaboration.

Driving Change in Large Organizations

Change management is a daunting task, especially in large bureaucracies. Caleb shared his insights on how to drive effective change by leveraging his military experience. "In the army, you learn quickly that adaptability and clear communication are crucial," he said. Caleb's approach involves understanding the unique needs of each organization, creating tailored strategies, and ensuring that everyone is on board with the change process. His success with the Digital Transformation Directive for the Canadian Army is a testament to his ability to lead and implement significant changes.

Remote and Hybrid Work: What Are We Doing Wrong?

With the rise of remote and hybrid work, many organizations struggle to find the right balance. Caleb highlighted some common pitfalls and offered solutions to improve remote work strategies. "We need to focus on trust and autonomy," he noted. By empowering employees and fostering a culture of trust, organizations can enhance productivity and employee satisfaction. Caleb also stressed the importance of leveraging technology to maintain seamless communication and collaboration in a remote setting.

Making Connections: Who Should You Talk To?

Have you ever attended an event and wondered, "Who should I talk to here?" Caleb's expertise in connecting people is invaluable in such situations. He shared tips on how to identify key individuals and set up meaningful conversations. "It's all about knowing who the connectors are and making introductions that matter," Caleb advised. By strategically networking and building relationships, individuals can maximize their impact and drive successful outcomes.

Driving Digital Change Insights from Caleb Walker

My conversation with Caleb Walker was enlightening and packed with actionable insights. His unique blend of military and tech experience offers a fresh perspective on digital transformation and change management. Whether you're a leader in a large organization, a veteran transitioning to a new career, or someone interested in digital transformation, Caleb's journey and expertise provide valuable lessons and inspiration.

To hear more from Caleb Walker and learn about his innovative work with Digital Insurgency, be sure to listen to the full podcast episode. You won't want to miss his tips on driving change, connecting communities, and navigating the complexities of remote work.

To connect with Caleb, visit his LinkedIn profile


Click here to hear the rest of the interview, follow us on the podcast!

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