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May 26, 2026

Humans In The Loop -- Tuesday, May 26, 2026

Humans In The Loop

Tuesday, May 26, 2026
Humans In The Loop
Your five-minute briefing on everything artificial intelligence.

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.

In today's newsletter
-> 113,000 tech layoffs and counting: the AI restructuring wave hits every sector
-> Your AI agents have a security problem nobody budgeted for
-> Salesforce and Google Just Declared War on Copy-and-Paste
Nasdaq
26,344
+0.2%
S&P 500
7,473
+0.4%
Nvidia
$215.42
-1.9%
Bitcoin
$76,587
-0.6%
OpenAI*
$300B+
private
Your 43% AI pilot
TBD
probably stalled
Per HCLTech, 43% of enterprise AI initiatives are on track to fail. Your mileage, and your board deck, may vary.
WORKING SMARTER, NOT EMPLOYED
113,000 Tech Jobs Gone in Five Months. Your Industry Is Next.
Photo by Boston Public Library on Unsplash
113,000 Tech Jobs Gone in Five Months. Your Industry Is Next.

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.

--


AGENTS OF CHAOS
Your AI Agents Can Now Be Hacked. Most Companies Have No Plan for That.

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.

--


FRENEMIES WITH BENEFITS
Salesforce and Google Teamed Up So Your Sales Reps Can Stop Switching Tabs
Salesforce and Google Teamed Up So Your Sales Reps Can Stop Switching Tabs

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.

--


Stat
PILOT PURGATORY
43%
The share of enterprise AI initiatives expected to fail, per a new HCLTech report covering 2026. Nearly half of enterprise leaders expect measurable ROI within 18 months, which leaves very little runway for the organizational chaos that tends to live between 'we bought the tool' and 'the tool works.'

What else is brewing
->EY and Microsoft committed $1 billion over five years to deploy enterprise AI at scale, with EY serving as 'Client Zero,' meaning it is testing the product on its own 400,000 employees before selling it to yours.
->Anthropic launched Project Glasswing, giving select companies including JPMorgan, Apple, and Cisco access to its unreleased Claude Mythos model to find critical software vulnerabilities, after it identified a 27-year-old bug in OpenBSD in early testing.
->AI venture funding in Q1 2026 hit $255 billion, surpassing the entire full-year 2025 total, with four of the five largest VC rounds in history closing in a single quarter.
->OpenAI was named a Leader in enterprise coding agents by Gartner, a distinction that would have meant nothing to most CEOs two years ago and now shows up in IT budget conversations every week.
->SpaceX filed publicly for a $75 billion IPO, joining OpenAI, Anthropic, and Oura in a crowded queue of AI-adjacent companies racing toward the public markets before the window closes.
Written by the Humans In The Loop desk. Sources: OpenAI, HCLTech AI Impact Imperatives 2026, Microsoft/EY press release, NPR, CBS News, TechResearchOnline, Layoffs.fyi via TechJournal.org, Crunchbase Q1 2026 report, HiddenLayer 2026 AI Threat Landscape Report, eSecurity Planet, The Hacker News, EU Council press release, Kelley Drye & Warren AI Regulatory Roundup, Kiteworks AI Regulation 2026, Salesforce/Google Cloud press release, TheNextWeb, Google Cloud Next '26 Wrap, Dell Technologies World 2026, Motley Fool/TheStreet market data (May 25, 2026).

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