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Skylar Payne
Skylar Payne

About me

Founder, Wicked Data LLC

I spent ten years building AI at Google, LinkedIn, and startups. Same pattern everywhere: smart teams, ambitious goals, and an AI nobody can explain when it breaks.

In every standup, every board meeting, every 2am Slack thread, the same question: "Why did the model do that?"

Usually nobody knew.

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What I do

I help engineering teams build AI they can actually understand and improve. I get into your codebase, look at your data, and build evaluation systems that turn "it feels broken" into "here's exactly what's wrong and how to fix it."

At Frigade, we achieved 40% better responses and 75% faster latency. At Sidecar, 35% better response quality. Real visibility into what your AI is doing, plus systematic ways to improve it.

Why evaluation matters

Most AI teams ship and pray. Eyeball a few outputs, say "looks good," hope for the best.

Then something breaks in production. A customer complains. Everyone scrambles—pulling logs, squinting at embeddings, tweaking prompts, hoping the problem disappears.

Teams that ship reliable AI do something different. They measure. They have dashboards. They know their failure modes before users find them. When something breaks, they have a hypothesis in minutes.

That's what I help teams build.

How I work

I'm not interested in writing reports that sit in drawers. I work alongside your team, building real systems with real code. The goal: make myself unnecessary. By the time we're done, your team owns everything and understands it completely.

Three ways we can work together:

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The short version

If your AI feels like a black box and you're tired of guessing, I can help. I've done this at companies big and small.

30 minutes on a call tells us both if this is a fit.

Schedule a free consultation

No pitch. Just a conversation about what you're building.