The role of the Chief Information Officer (CIO) has evolved beyond maintaining IT systems to encompass leadership in navigating ambiguity, enabling the responsible use of generative AI (GenAI), and shaping digital ethics in real-time. In a podcast episode, Mark Booth of Perdue Farms and Mark Goldberg of the British Columbia Lottery Corporation discuss how modern CIOs must act as listeners, risk-takers, and change enablers, emphasizing the criticality of a holistic approach to AI that integrates data, business outcomes, and technology. Both CIOs illustrate the practical application of GenAI in their respective industries—agriculture and gaming—demonstrating its potential to enhance customer understanding and responsible gambling through projects rooted in data-driven insights. They stress the importance of managing the complexities of GenAI, noting that success comes from embracing uncertainty and aligning technology with strategic business goals. Ultimately, they highlight that effective GenAI leadership arises from fostering systems, strategies, and cultures that support AI's integration into decision-making processes, underscoring the role of clear vision and purpose in achieving meaningful transformation.