Humans In The Loop -- Tuesday, May 26, 2026
Happy Tuesday. The AI industry spent Memorial Day weekend deploying agents, cutting headcount, and lobbying regulators, which is basically what the rest of us call a long weekend.
Over 113,000 tech workers have been laid off across 179 companies so far in 2026, with April marking the worst single month in two years, and the pace is still accelerating into May. The companies doing the most cutting are simultaneously making the largest AI investments in history, which is not a contradiction so much as a mission statement.
This is not just a tech story. Citigroup is targeting 20,000 job reductions through AI-enabled automation of middle-office functions. C.H. Robinson, the logistics giant, already cut 1,400 jobs after deploying AI tools for pricing, scheduling, and shipment tracking. The question for every CEO is no longer whether your industry is affected, but whether you are managing the transition or being managed by it.
- Coinbase CEO Brian Armstrong warned that mass AI-driven layoffs are coming to 'every company,' then immediately announced a 14% workforce reduction at his own.
- Nearly 48% of layoffs tracked through April 2026 were explicitly attributed to AI and workflow automation, per Nikkei Asia analysis.
- Companies building AI, like OpenAI and Anthropic, are hiring aggressively. Companies being disrupted by AI are shrinking. The dividing line is becoming very clear.
🧠 Ha's Take: The AI race is no longer about whether companies can adopt the technology. It's whether leaders can help their people adapt as quickly as the technology is changing. Most companies have an AI roadmap. Far fewer have a workforce roadmap.
Giving an AI agent access to your CRM, email, finance systems, and cloud infrastructure is like handing a new employee a master key on their first day, except this employee never sleeps, never asks questions, and can be tricked by a cleverly worded email. Security firm HiddenLayer found that 1 in 8 companies has already reported an AI breach tied to agentic systems, and 76% of organizations now cite 'shadow AI,' meaning employees using unauthorized AI tools, as a definite or probable problem, up 15 points from last year. Meanwhile, only 24% of enterprises have a dedicated AI security governance team.
The specific threat getting the most attention is prompt injection, where a bad actor embeds hidden instructions in a document, email, or website that your AI agent reads and obeys. IBM's 2026 X-Force report found a 44% rise in attacks exploiting public-facing applications. Even the tools you trust have cracks: researchers found a critical remote code execution flaw in Google's Gemini CLI this month, and a separate malicious campaign targeted SAP npm packages to steal developer credentials. The Gemini flaw has been patched, but the message is clear: AI infrastructure is now an attack surface, and your security budget was probably written before anyone thought to include it.
🧠 Ha's Take: We're entering a phase where the limiting factor for AI adoption is no longer model capability. It's organizational maturity. The question isn't whether AI agents can do the work. It's whether companies have the governance, processes, and leadership discipline to deploy them safely at scale.
The average employee loses two hours a day toggling between apps, a statistic that every productivity vendor has been citing for years while quietly selling you another app to toggle between. Salesforce and Google Cloud announced an expanded partnership that lets AI agents run end-to-end workflows across Slack, Google Workspace, Salesforce Agentforce, and Google's Gemini Enterprise platform, without copying data between systems. Gemini-powered reasoning for Agentforce is now available in May, and over 1,400 customers are already using Gemini inside Agentforce.
The practical implication for a non-tech CEO: if your company runs on Salesforce and Google Workspace, your salespeople can now have an AI agent that pulls CRM data, drafts follow-ups, updates pipeline records, and surfaces deal risks, all from inside Gmail or Slack without re-entering anything. Wayfair's CTO called it the foundation of their 'Agentic Enterprise,' embedding agents across customer service and logistics. If you are a retailer, a financial services firm, or really any company with a sales team and a CRM, this is the upgrade your ops team will ask for by Q3.
🧠 Ha's Take: The biggest productivity killer in most organizations isn't lack of effort. It's workflow friction. Every tab switch, copy-paste, status update, and CRM field steals a little bit of human attention. The most valuable AI applications won't replace people. They'll remove the busywork that gets in the way of people doing their best work.