As organizations across Oregon and beyond grapple with rapid advances in artificial intelligence, leaders are being asked to make decisions that go far beyond technology adoption. For Tim Winner, Chief Operating Officer of the Technology Association of Oregon (TAO), the challenge, and opportunity, lies at the intersection of AI, leadership, and organizational transformation.
Tim Winner
“AI is no longer a future concept - it’s already shaping how leaders plan, communicate, and make decisions,” Winner says. “What’s missing for many organizations isn’t access to tools, but the leadership confidence to use them thoughtfully.”
Winner brings deep experience working with technology-driven organizations navigating change. His support of Portland State University’s Strategic Leadership in the Age of AI program reflects a belief that today’s executives need more than technical know-how - they need practical frameworks and a leadership mindset that keeps humans firmly at the center of innovation.
“The most effective leaders I see don’t treat AI as a replacement for human judgment,” Winner explains. “They treat it as a partner, one that can surface patterns, spark creativity, and free teams from low-value tasks so they can focus on strategy and vision.”
That philosophy aligns closely with the goals of the program, which is designed to help leaders integrate AI into both day-to-day operations and long-term strategy with intention and clarity. According to Winner, programs like this are critical because they meet leaders where they are.
“Leaders don’t need to become AI experts overnight,” he says. “They need grounded, realistic ways to start small, learn fast, and build a culture that’s open to experimentation.”
Winner emphasizes that AI adoption is ultimately a leadership issue, not a technical one. “The organizations that succeed will be led by people who understand how to ask better questions, guide their teams through change, and use AI to enhance - not overshadow - human insight.”
For executives considering their next step in an AI-driven world, Winner’s advice is clear: invest in leadership development that connects technology to real organizational impact. “Programs like Strategic Leadership in the Age of AI help leaders build confidence, not just competency, and that’s what will define success in the years ahead.”
Seats are limited, register now to be part of the upcoming executive program here.