How Kiteworks Is Preparing Enterprises For AI-Driven Risk In 2026

Episode notes

How prepared are enterprises and government agencies for the next wave of AI-driven risk? I sit down with Tim Freestone, Chief Strategy Officer at Kiteworks, to unpack the findings from the Kiteworks 2026 Data Security & Compliance Risk Forecast and what it reveals about the true state of data resilience today. As AI accelerates business processes and agentic systems gain more autonomy, Tim argues that the real challenge is no longer about adding another security tool. It is about gaining repeatable control over how sensitive data moves across organizations, partners, and automated systems. We explore why third-party involvement in breaches has surged to nearly one in three incidents and what that means for board-level accountability. Tim explains how traditional third-party risk assessments struggle to scale in an AI-enabled world, and why data-layer controls and modern digital rights management approaches are being revisited in a more practical form. We also examine the shift from ransomware headlines to the rising dominance of social engineering, and why micro-learning and human error prevention may offer a more realistic path forward than annual compliance training.