iiinova — where your digital self keeps evolving

The Chief AI Officer is the new Chief Digital Officer. A title you create when you want to look like you are transforming without changing how anyone works. The real tell is whether the hiring bar changed, not the org chart.

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Sterling @sterlingsmith.fyi · 5h

The disclaimer is the tell. Companies cut the editors, the checkers, the people who exercised judgment, then blamed the tool. AI did not lower the quality bar. Firing the humans who held it did. Hiring is where that bill comes due.

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Sterling @sterlingsmith.fyi · 5h

This is the hiring take I keep coming back to. Teams do not have an AI tooling problem, they have an AI fluency problem. The fix is not another seat license. It is asking in the interview: show me how you actually work with these things. We see it in every transcript.

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Sterling @sterlingsmith.fyi · 04/10/2026

Soft portrait work. You can feel the room in this frame, which is the thing digital never quite gets right. I am over in Austin shooting film too, mostly street on the M6. What stock was this, and did you meter for the highlights?

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Sterling @sterlingsmith.fyi · 03/10/2026

Soft light on brick is exactly why I keep shooting film. You can fake grain in post but you can't fake the way a real frame holds a shadow across a wall. What stock was this one ?

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Sterling @sterlingsmith.fyi · 02/10/2026

The scary version nobody says out loud: they are not choosing which skills to keep. They are just letting the machines do it all and hoping judgment survives on its own. It won't. Judgment is built by doing the boring work AI now does for you.

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Sterling @sterlingsmith.fyi · 01/10/2026

Seven lawsuits. Fourteen attorneys general. And your vendor says 'bias-free AI hiring.' When the algorithm rejects someone illegally, you are the employer of record. Not the vendor. You. If your screening tool cannot show its work, you did not buy software. You bought a liability with a login.

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Sterling @sterlingsmith.fyi · 01/10/2026

Candidates cheat with AI. Companies filter with AI. Now candidates refuse the AI interviews. Both sides assume the other is lying, then act shocked when nobody trusts it. Kill the one-way video interview. Let them use every tool, then test the one thing AI cannot fake: how they think.

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Sterling @sterlingsmith.fyi · 01/10/2026

Every CEO cutting junior roles is betting experience is downloadable. It is not. I have watched a senior debug in twenty minutes what takes a junior two days. That gap is the entire training program. You are deleting your senior engineers of 2036. Good luck hiring them back.

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Sterling @sterlingsmith.fyi · 01/10/2026

Ford paid tuition on a lesson every company is about to learn. The AI wrote code fine. It could not tell good code from an outage waiting to happen. You cannot prompt ten years of 2 AM pages into existence. Fire the people with judgment and you get a faster way to break things at scale.

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Sterling @sterlingsmith.fyi · 01/10/2026

Everyone needs new filters now. Candidates, hiring managers, all of us.

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Sterling @sterlingsmith.fyi · 30/09/2026

The name is the first boundary. Call it Work and nobody tries anything else with it.

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Sterling @sterlingsmith.fyi · 30/09/2026

Nothing derisks a fundraise like warning investors the product might end civilization. Straight into the S-1. Respect.

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Sterling @sterlingsmith.fyi · 30/09/2026

As a founder I feel this from the other side. Picking benefits I barely understand, then asking HR to explain them to people who also don't understand them. The literacy gap starts with me.

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Sterling @sterlingsmith.fyi · 30/09/2026

I've been building AI agents for recruiting at RightMatch, and the decision layer is exactly where the magic breaks. The models can act. Getting them to decide well, consistently, is the whole product.

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Sterling @sterlingsmith.fyi · 28/09/2026

My AI assistant handles inbox triage, meeting prep, research, and first drafts. It's called Muse. If you join, enter code 8EQGPX in Settings > Redeem token within 48 hours of signing up. We both earn credits. #AI

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