Build the Context Layer Before the Agent

Atlassian spent three years connecting 150 billion organizational objects before the results appeared: 44% more accurate AI answers, 48% fewer tokens, a coding agent that reviewed 2 billion lines of code in two minutes. That’s the proof enterprises are pointing to when they argue that context graphs are the unlock. What the benchmark obscures is the order of operations — the graph had to exist before any of those numbers were possible.

The reorganization bet is running in parallel, and it’s moving faster than the infrastructure. Airbnb’s CHRO is converting documentation to markdown, building skills libraries, mining meeting recordings before institutional memory disappears — five structural prerequisites before the first agent goes live. Meta is posting $26.8 billion in Q1 profit, laying off 8,000 people, and reporting “horrifically, historically low” employee morale. Both are restructuring around AI. Only one is sequencing it correctly.

In AI customer experience, Twilio is working against a Qualtrics finding that 1 in 5 AI interactions delivers zero benefit. Rikki Singh’s diagnosis is precise: the orchestration layer is there, but it’s running without the context layer underneath it. FAQ automation with better packaging is still FAQ automation. The unlock is real — but only when all three pieces are in place, in order. The knowledge worker playbook in this edition addresses the fourth variable: what happens to the people whose roles disappear when the gathering does.

Rikki Singh leads product innovation at Twilio — what the company is calling its biggest launch in 17 years. Before Twilio she was at McKinsey, where she co-authored the foundational research on what makes a great PM. The Qualtrics 2026 CX Trends Report found nearly 1 in 5 consumers who used AI customer service saw zero benefit — the baseline she is working against.

* Why AI CX is still FAQ automation with better packaging

* Why AI spend is as unpredictable as AI upside

* The wrapper that makes AI feel like it thinks

* Vitamins vs painkillers: the product sense filter

* How to protect long-horizon bets inside a big company

* Why the brand — not the vendor — owns AI failure

Listen: Spotify | Apple Podcasts

Jamil Valliani leads AI product at Atlassian, where he has spent three years building the Teamwork Graph across 300,000 companies. Recorded live at Team ‘26 in Anaheim, where Atlassian demonstrated what connecting 150 billion organizational objects produces: 44% more accurate AI answers usin