In July 2025, Jason Lemkin, founder of SaaStr and a well-known investor in enterprise software, decided to publicly test one of AI’s most repeated promises: that anyone can build an application without programming, simply by giving instructions to an agent. He chose Replit, a platform presented as the safest place to do so. He gave himself 12 days and worked with real…
DetailsEvery CIO can produce an AI adoption dashboard: licenses purchased, seats activated, prompts submitted per week. Boards ask for these numbers, vendors report them and they climb every quarter. What none of them show is whether the tool earned a durable place in anyone’s work. A license counts distribution, not value. An activated seat tells…
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In an August 2026 Gartner report, 40 percent of C-level executives say their organizations have “operationalized AI in some business processes,” yet only 13 percent say they have “achieved measurable results and are scaling AI across the organization.” This disconnect reveals a frequent reality: AI may have been “hired”, but companies haven’t onboarded it effectively.…
DetailsGoogle seems to be making a strategic play to control the AI infrastructure layer, not just roll out another shiny new agent. At its Gemini at Work 2026 event this week, the tech giant unveiled what it calls a “single, universal agent” and API in Gemini that can be kicked off from a simple prompt…
DetailsFor decades, cybersecurity benefited from a constraint that was easy to take for granted: Attackers were limited by human capabilities. Finding vulnerabilities and developing reliable exploits required expertise. Reconnaissance, lateral movement, and adaptation took time and effort. That friction created something valuable for security practitioners: a window in which they could identify and assess risk,…
DetailsI have audited enough celebrated technology rollouts to notice a quiet omission across the industry: nobody talks much about what happens to the unit economics once the pilot ends and the software enters daily production. I have anonymized the company and changed identifying details for confidentiality, but the operating economics and workflow behaviors below are…
DetailsIn my experience, where you place product management is as critical as whom you hire and how you train them. A team expected to serve the whole organization needs the influence and independence to act for the whole organization. My view comes from working in companies ranging from trillion-dollar enterprises to startups, and from ongoing…
DetailsEager to incorporate agentic AI into their work, employees are taking matters into their own hands, creating their own AI agents, regardless of organizational approval, and a not insignificant number of those creations could have devastating consequences if IT leaders don’t get ahead of the trend. According to a recent survey by engineering staffing firm…
DetailsOver 20-plus years in the enterprise trenches, I’ve watched multi-million-dollar technology transformations stumble over the same blind spot. We spend months debating cloud architectures, database benchmarks and vendor feature matrices. But the tech itself? That’s rarely where the real bleeding happens. The real pain arrives later, in the messy organizational wake: Who actually controls this…
DetailsI argued in my last column, The case and model for real-time AI cost visibility at the infrastructure layer, that the AI measurement problem looks to be finally solved as a technical matter, and that companies can now manage AI as a strategic investment rather than a pay-and-pray experiment. That’s the defining shift for the…
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