Operating AI

Launching AI is the easy part. Keeping it compliant, valuable, and under control is the real work.

124 articles

Frameworks

Your Docs Have Two Audiences Now. One of Them Counts Tokens.

Addy Osmani named it Agentic Engine Optimization. Your information architecture is now a governance surface for AI agents, not just humans.

Apr 13, 20267 min read Read more

Your AI Agent's Judgment Is Unmeasured. A PM Rubric Shows What to Fix.

Jeff Gothelf's 4-dimension rubric for product judgment applies directly to AI agents. Nobody is scoring agent decisions. Here is how to start.

Mar 26, 20268 min read Read more

You Cannot Govern What You Cannot Simulate

Enterprise world models are the missing governance layer. Without simulation, managing AI agents is guesswork at scale.

Mar 23, 20267 min read Read more

The 5Rs Framework: Why Most AI Initiatives Fail

AI projects fail due to organizational deficiencies, not technical ones. The 5Rs Framework transforms pilots into business results.

Dec 19, 20258 min read Read more

Essays

Points of View

Explore Operations Partnership

Running AI in production. Monitoring, compliance, and ongoing value extraction.

Explore Operations Partnership

Operating AI

Your Docs Have Two Audiences Now. One of Them Counts Tokens.

Your AI Agent's Judgment Is Unmeasured. A PM Rubric Shows What to Fix.

You Cannot Govern What You Cannot Simulate

The 5Rs Framework: Why Most AI Initiatives Fail

Essays

The Agent Integration Tax and the Lattice of Legibility

Anthropic Just Shipped Ten Finance Agents. Each One Drafts a Regulated Artifact.

Vision Agents Cost 45x More Than MCP. Building One Is Now a CFO Conversation.

You Can Adopt AI Individually and Still Not Learn as a Company.

Two Ad Clouds Went MCP This Week. Your Media Plan Is Now an Agent Plan.

Off-Site Is the New Moat. Your Domain Is Half the Story.

AI-Native Operating Maturity: Hiring, PM, and Support Get Rebuilt at Once

82% of Your Message Reaches the Buyer Through a Summary You Did Not Write

The Stealth Tax of Model Upgrades: What GPT-5.5 Actually Costs

Five Companies Just Named the AI-Search KPIs They Actually Track. Here's the Decision Frame.

Builders, Shippers, Coasters: How 900 Engineers Actually Pay for AI in 2026

Anthropic Runs at One Nine. Meta's Answer Is Skills as the Throughput Substrate

Microsoft Said the Quiet Part: Per-Seat Licensing Just Died on an Earnings Call

When the Agent Is Its Own Procurement Department

When the Vendor Says 'Don't Let AI Do the Synthesis'

Verification Is the New Compute Cost — and Your Vendor Controls the Eval

Marketing's MCP Moment: An Agent Can Burn a Daily Budget in 15 Minutes

Netflix's 600-Synopsis Golden Set: A Production Methodology for LLM-as-a-Judge

AI Eliminated the Friction That Built Your Best Teams

AI-on-AI Reverification: The Harness Lands in Incident Response

The Attribution Loop You Can't Audit

Designers Are Now Governance Engineers — They Just Don't Have the Title

Marketing's Three 2026 Questions Just Got Their First Real Data

Your Coding Agent Approved Its Own Overage 97% of the Time

Sierra Hires Differently. Meta Cuts Differently. 95% of AI Pilots Still Fail.

When You Certify an Agent, You Change What It Optimizes For

Cloudflare Just Published Its Own Case Study

AI Industrializes Coordination. Not All of It.

HR Has an AI Governance Surface Now. McKinsey Just Gave It Numbers.

Marketing's Governance Stack Is Real. It's Also Asymmetric.

Four Reports, One Week, One Measurement Gap

Credit Governance Is the Template for AI Agent Spend

Enterprise MCP Just Crossed the Engineering Line

Your Marketing Team Just Became a Governance Team

The Workflow Is the Governance Primitive

Four Launches, One Week, One Control Taxonomy

Cost Governance in the Flat-Fee Era: The 3-Layer Framework You Should Have Shipped Yesterday

Engineering Has Cloudflare. Marketing Has Nothing.

Team Alignment Is the New Bottleneck

Trust Is the UX

The Accountability Asymmetry: Why Agents Buy Small and Humans Still Buy Big

Marketing Just Had Engineering's 2024 Moment

Execution Speed Was the Moat. Learning Speed Is.

Position One Is the New Page One: Inside Google AI Mode Shopping

Designers as Conductors: AI Is Rewriting Design's Operating Model

164 Million Purchases Exposed AI Traffic's Conversion Problem

Your Content Moderator Explains Itself Fluently. Its Explanations Are Wrong.

99.5% AI Adoption at a $32B Company. The Secret Wasn't the Technology.

Your Agent Forgets Everything. Here Are Three Ways to Fix It — and One Question Nobody Is Answering

Your Agent Skips Its Own Memory. That Is a Governance Failure.

Governed Agent Infrastructure at Scale: What KernelEvolve and AWS DevOps Agent Actually Prove

Open Models Crossed the Agent Threshold. Now What?

Platform Coupling: Why AI Cites What It Owns, Not What You Publish

Silent Drift: The Agent Failure Mode Nobody Named

The Infrastructure Between Agent Demos and Agent Operations

From Tribal Knowledge to Governed Intelligence: Meta Runs 50,000 Daily Analyses

The Design Twin Problem: Who Governs What AI Builds?

AI Governance Is Leaving the Engineering Silo

Mandatory Agent Review: What VS Code's 2.2x Commit Growth Actually Required

The Two Governance Problems in Agentic Commerce

Design Debt in AI Products: When Interface Decisions Shape What Users Believe

ISO 42001: When AI Governance Becomes a Product Feature

Platform Governance Is Splitting: Reddit Labels Bots While ChatGPT Sells Them Ad Space

Just One More Prompt: The Dopamine Trap of AI-Assisted Work

When AI Mandates Become Org Charts: Meta's Structural Bet

The 400-Dollar AI Team That Nobody Governs

The Simulation Toolchain Arrives. The Validation Infrastructure Does Not.

Your Security Scanner Was the Attack: What Syscall-Level Monitoring Reveals About Agent Runtime

Evaluation-Driven Development: The Missing Operations Layer for AI Agents

The Week Agent Infrastructure Went Mainstream

What Tens of Millions of Agent Sessions Reveal About Misalignment

Stripe's Blueprints: How Deterministic Rails Make Agentic Code Safe at 1,300 PRs Per Week

Agent Memory Self-Design: Who Validates the Validator?

Running AI Agents at Scale: What Stripe, Cloudflare, and Istio Teams Actually Do