Nitro Software: The Hidden AI Risks Lurking In Everyday Document Workflows

What happens when the biggest AI security risk isn't the technology itself, but the people using it? In this episode, I sit down with Cormac Whelan, CEO of Nitro Software, to discuss why organizations need to rethink their approach to AI adoption. With research showing that 68% of C-suite executives are bypassing approved AI tools in favor of their own, we explore how an "ask forgiveness, not permission" culture is creating new security and compliance challenges for businesses around the world. Cormac shares why successful AI adoption begins with business outcomes rather than the latest model or headline-grabbing announcement. Drawing on his experience leading Nitro and previously building an AI company acquired by Apple, he explains why AI should be an enabler rather than the destination, and why organizations that focus on trust, transparency, and practical business value will ultimately pull ahead. Our conversation also looks at why documents, contracts, PDFs, and e-signatures have become some of the most overlooked parts of the enterprise AI conversation. As AI systems increasingly interact with sensitive business information, protecting document workflows is becoming just as important as securing networks and endpoints. We also discuss how European privacy standards are becoming a competitive advantage rather than simply another compliance requirement, how to separate genuine AI innovation from expensive security theater, and why AI should quietly improve the way people work instead of becoming the center of attention. If you're trying to balance AI innovation with security, governance, and business value, this conversation offers practical advice without getting lost in the hype. After listening, I'd love to hear your thoughts. Is your organization focusing on outcomes first, or is it still chasing the latest AI headline?