Commanding the Transformation: A Leadership Playbook for AI Adoption in the Modern Organization
Successful AI adoption is 10% technology and 90% organizational change—and most organizations are failing at the 90%. In this dynamic, experience-driven session, we will cut through the hype and get honest about what it actually takes to move AI from promising pilot to measurable business impact. Drawing on nearly three decades of technology leadership and his background as a U.S. Army Ranger, Shawn brings a battle-tested perspective to the modern boardroom: the same principles that forge elite units into high-performing teams are exactly what today's organizations need to win the AI transformation. This session tackles the hardest problems leaders face right now, securing genuine cross-functional buy-in, navigating the cultural resistance that quietly kills AI initiatives, and building the organizational muscle to sustain change long after the kickoff meeting ends. We will explore real-world frameworks for workforce strategy, the evolution of executive decision-making in an AI-augmented environment, and what it actually looks like to build a culture of innovation that is not just a slide in a deck. You will leave with a concrete roadmap for transitioning your teams from fearing AI to mobilizing it as a force multiplier for human talent, and a clearer sense of your own role as the leader who makes that shift possible. Whether you are navigating your first enterprise AI initiative or trying to rescue one that has stalled, this session will give you the language, the leadership tools, and the strategic clarity to drive AI adoption that shows up on the bottom line. Mission-focused. Results-driven. Built for leaders who are serious about winning.
Shawn N. Olds is a business leader and advisor with deep experience leveraging technology to start, run, fix, and rapidly evolve and enable established businesses as well as startups. With a focus on AI over the past decade, Shawn excels in developing, deploying, and commercializing technology solutions as well as helping companies develop business strategies to use the most appropriate technology to solve their specific needs. His leadership experience spans private enterprise, government service, and higher education. Shawn is a Managing Director and Chief AI Officer at The ONE Bow River National Defense Fund a private equity fund focused on supporting innovative solutions to strengthen national defense. Previously Shawn was the Co-Founder and Founding CEO of boodleAI, an artificial intelligence platform that launched both a traditional AI platform for nonprofits and sales teams and later a Generative AI tool focused on the workplace and the higher education vertical. Shawn has held executive, board (Independent Director), advisor, and angel investor positions in multiple organizations. In 2024 he was inducted into the American Society for Artificial Intelligence. Shawn holds a Computer Science degree from West Point, an MBA from The Kellogg School of Management, and a JD from The Northwestern Pritzker School of Law.