HeyJaredBetween Roles
The gap between AI announcement and delivery. POCs that don't scale. Organizations reskilling faster than tools change. Retail and ecommerce systems breaking in production. Roles shifting mid-flight. 20+ years in the middle, no frameworks.
- Indexed issues, last 90 days
- 9
- Latest publication
- Sep 29, 2026
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- Earliest in this view
- Jul 8, 2026
Latest issues
We changed a line of config. The system broke anyway. (opens the original)
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We were on a call to sign off on a model upgrade. One stakeholder asked, plainly: “How much time do we save with the newer model, and at what cost?”Someone else had a different question. Their team was using the current model to summarize analytics. Getting good results. They asked: do we still need to upgrade?Nobody answered either question cleanly. The tech side could talk about output quality, relevance, accuracy: the newer model was better, measurably, on paper. But “better on paper” isn’t t
Debugging is Disappearing (And Nobody Notices) (opens the original)
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A retail AI system I worked on debugged itself perfectly. The margins looked right and the recommendations came through. Everything worked except one point: nobody knew why it worked.The person who shaped the system spent months testing it. Seeing where it behaved well, where it needed another look. Building confidence in what it could and couldn’t do. Then they moved to a different store.The next person inherited the system but not the months of testing. Same recommendations. Different caution.
AI Didn’t Break the Migration. It Compressed 2 Years of Discovery Into 3 Weeks. (opens the original)
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A quick note before this one: this isn’t an AI-failure story. It’s about what happens to the BA role once AI compresses a discovery process that used to take years into a few weeks.<a class="image-link image2 is-viewable-img" href="https://substackcdn.com/image/fetch/$s_!NpWR!,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F74cda643-7c5c-420a-9c6b-35da5fd
AI changed the work. Why didn't accountability change? (opens the original)
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The person validating, approving, or supervising AI is often carrying responsibility for a system they don’t fully control.I’ve been thinking about this while watching how AI is changing some roles around software delivery and retail. We spend a lot of time talking about the work AI is taking over. What I keep wondering about is the work left behind—and who’s expected to own the result.Take a business analyst. A few years ago, a BA spent days talking to users, understanding a process, resolving
Your role didn’t disappear. The work moved. (opens the original)
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A few weeks ago, I was catching up with a friend who works with engineering leadership in an IT services company. We ended up talking about a AI proof of concept they had recently shown to one of their existing customers. I assumed that the conversation would stay on the technology, features, quality but It didn’t.The first few questions were predictable. Was the output good enough? How much context did it need? Would customers trust it with their code and documentation? Those lasted maybe not m
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