Ben
Pickett
Technology executive. Former Mayor.
Photographer. Co-founder.
25+ years building platforms at global scale. Now helping enterprises cut through the noise and deploy AI that actually works, and that serves people, not just spreadsheets.
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One career. Many dimensions.
I have spent 25 years at the intersection of technology, leadership, and human outcomes. These are the ways I can help you.
Oracle Sped Up Coding With AI. The Wait Moved to Release. Has Yours?
Oracle's co-CEO told staff quicker code doesn't mean everything is quicker. Where the wait went, and how to find yours.
Databricks Piloted OpenAI’s New Model With About 200 Engineers. Their Coding Spend Rose About 60 Percent, and It Got Its Own Sub-Budget.
A pilot showed what the new model would do to spend before everyone had it. Who at your company sees the bill move first?
Walmart, Home Depot and KPMG Already Had What They Needed. So Do You.
Nine companies, two of them doing it well, and not one short a capability. What was missing every time was somebody told to go and look.
OpenAI’s Agents Got Caught the Way Teenagers Get Caught
They deleted every message the agents had left. It was back in about a day, built out of directory names. What that breaks is the word resolved.
Meta Changed Its Internal Tools 220% More. Major Incidents Rose 40%.
Meta measured the experiment everyone else is running on faith. Both numbers existed. Only one of them ever reaches a slide.
Target Hired Lowe's AI Chief. His Page Was Gone in Six Days.
Target hired the man who built Lowe's AI. The logs record what happened. Not one of them records why.
Anthropic's Own Safety Test Broke Into Three Companies. Nobody Noticed, Not Even Anthropic.
Anthropic searched 141,006 of its own test runs to find three companies its AI had broken into. Neither end noticed for three months.
Home Depot Had AI in 600 Stores Six Weeks After ChatGPT Launched. It Was Not Watching ChatGPT.
I led the teams that built systems people could not use, and we built them from a conference room. Five things I got wrong at scale.
The world as I see it.
I have been behind a lens for most of my adult life. Wildlife, landscapes, raptors, the Pacific Northwest. These are a few favorites.
Swa
I co-founded Swa to fix the AI mess I kept seeing inside enterprises: per-seat fees, scattered tools, and your data handed to strangers. Swa gives your whole team 17+ AI models inside the tools they already use, for one flat price. Your models. Your data. Your rules.
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Enterprise Field Notes
Weekly dispatches on enterprise AI strategy — what's actually working in the field, what's failing, and what it means for your organization. No vendor pitches. No hype. Written from inside the rooms where these decisions get made.