HeyJaredInsight On
Insight On is the podcast for leaders who make technology decisions — and need them to deliver. From CEOs and CIOs to the next wave of decision-makers in strategy, operations, and IT, you're invited into the inner circle of business and tech leadership.
- Indexed episodes, last 90 days
- 5
- Latest publication
- Sep 10, 2026
- Audience
- Checking…
- Earliest in this view
- Jul 8, 2026
Latest episodes
The Tokenomics Behind Company-Wide AI That Actually Scales | EP47 (opens the original)
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As AI labs shift to usage-based consumption pricing, the math on per-seat licensing is getting harder to defend. In this episode, Shana Meyers, Director of Global Business Solutions and Distinguished Technologist at Insight , breaks down how Insight built its Enterprise AI Hub — a platform that gives every employee access to multiple AI models through API-based token consumption, at roughly one-tenth the cost of individual licenses. You'll hear how a rejected — but successful — pilot became the
The Hidden Cost of AI That Never Shows Up on the Invoice | EP46 (opens the original)
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AI token costs just changed — and the invoice is the least of your problems. Juan Orlandini, CTO of North America at Insight, breaks down what metered AI pricing is actually exposing about the structural assumptions your organization made when tokens were cheap or free. You'll walk away knowing how to read the real damage — the hiring decisions, workflow expectations, and delivery timelines that were built on subsidized pricing — and what to do about it before it compounds. Juan covers model rou
Gen Z Has a Question for Employers — How Are You Using AI? | EP45 (opens the original)
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AI is reshaping entry-level work fast — and the generation walking into your workforce has already formed opinions about how you're handling it. Four college interns share what they actually think about AI, career development , and the skills that matter most when the task layer disappears. In this conversation, you'll hear why a company that doesn't use AI is a red flag to this generation, how AI freed up intern time for human connection rather than replacing it, and what one intern learned spe
The Org Decision Most CFOs Are Too Cautious To Make | EP44 (opens the original)
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What does it actually take to move from AI adoption to AI transformation? It starts with a structural decision most organizations haven't made: giving someone AI transformation as their only job. Alex Pugh, d irector of f inance AI o perations at Insight, sits inside exactly that model — a dedicated AI ops team embedded within a single business function. This conversation gets into the accountability structures, the hard-won use case lessons, and the one metric that tells you transformation has
You Can No Longer 'YOLO Mode' It. Here's How To Adapt to GitHub Usage-Based Billing. | EP43 (opens the original)
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GitHub Copilot's billing model changed on June 1 — and most enterprise teams are about to see their first full bill under the new system. For many organizations, it'll be the first real look at what AI adoption actually costs at scale . The shift from flat-rate to usage-based billing sounds straightforward. Pay for what you use. But what your team is "using" turns out to be a lot more complicated than anyone expected — and the habits that felt like strong AI adoption six months ago are the same
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