This study explores the intricate power dynamics between Chief Information Security Officers (CISOs) and Chief Information Officers (CIOs) within modern technology organizations, against the backdrop of digital transformation and cybersecurity challenges. Recognizing the evolving roles of CISOs from technical specialists to strategic influencers, the research highlights the necessity for a collaborative approach between CISOs and CIOs to enhance organizational cybersecurity. Through qualitative interviews of 17 top IT leaders including 8 CISOs and 9 CIOs, the study identifies themes such as the impact of regulatory compliance and industry nuances on budget authority, revealing the complex interplay of power, influence, and strategic alignment in the executive suite. This research contributes to the discourse on organizational leadership and cybersecurity, offering insights into enhancing collaboration between CISOs and CIOs to bolster organizational security postures.