David Barry

Copilot Cowork is Microsoft's most capable agent yet. The gap isn't the tech: it's the governance, accountability and data hygiene most enterprises don't have. Microsoft has built an AI agent that can act across an entire organization. The problem is most organizations aren't ready to manage a human workforce doing the same tasks, let alone an autonomous agent.

Block, AWS, Salesforce – just a few of the companies blaming layoffs on AI productivity gains. But the numbers don't add up. When Jack Dorsey announced that Block would eliminate more than 4,000 jobs, nearly half its global workforce, he did not describe it as a correction, but as a vision: AI-driven efficiency, faster teams, leaner operations. The language was forward-looking, almost evangelical.

Enterprises are vetting AI agents like software vendors. But an agent that can act across your systems isn't software. It's a delegation of authority. Businesses have been using the same SaaS software procurement model for the last 10-15 years. The vetting centers around a core assumption: the software is built to respond to human inputs. The SaaS procurement playbook was never designed to handle AI agents. Yet enterprises are still applying it to a technology that doesn't behave like software.