Dearborn Labs Introduces AI Chiefs of Staff for Executives

This title was summarized by AI from the post below.

Each executive at Dearborn Labs recently got a new Chief of Staff. They are a series of AI agents trained on insurance domain expertise, the shared context across the company, and how each individual likes to operate and communicate. Mine is Jarvis. I spent the past year building and teaching it how to run my operating rhythm. Jarvis knows my voice, my priorities, how I make decisions. It knows how we think about running an insurance business. It knows the context and history of our business specifically. Each decision and piece of feedback makes it sharper. The outcome? I now automate everything that doesn't require a human. The rest of my time goes to the work that does. When the team saw how I used Jarvis, they built their own. Within a few weeks, our leadership meetings had more agents than humans in the room. Jen Crutchfield built Atticus for regulatory and legal research. Adam built Flynn for product and technical work. Seth built Roz for insurance product strategy. Jen Kemp built Maven for financial work. Each one is an expert in its domain and built on our company's institutional knowledge. Each one carries yesterday's context into tomorrow's decisions. The takeaway for me was straightforward. The AI model matters, but the differentiator is what you wrap around it. Your decision frameworks. Your domain expertise. How your specific organization actually operates. Decision infrastructure; that layer is what turns a general-purpose model into something that compounds. It's what we're building at Dearborn Labs. I wrote up more about how Jarvis works. Link in comments.

Very cool. I built a small team of them. My Chief of Staff is named Moneypenny. Then you got Sharon, Rhonda, Zoe and Stu.....almost forgot Parker. Wanna hear the crazy part? They have meetings with each other at night and in the morning I get a brief and suggestions for process improvements.I'll have Moneypenny ping Jarvis.

What tool did you use to build these?

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Fascinating shift. The real advantage is not just using AI but embedding your decision frameworks and institutional knowledge into it. That is what turns automation into a true multiplier for leadership and execution.

Kyle, this is an incredible example of aligning AI with operational excellence. The focus on decision infrastructure and domain-specific context truly highlights the power of tailored innovation. 🚀

I definitely agree with you about cleaning up an organization's data infrastructure to get the most out of agents. I have to ask - was Jarvis named after J.A.R.V.I.S.? 😉

The bit about training it on how each individual likes to operate is the part most people will gloss over, but it's probably the hardest part to get right. I've found that the generic 'AI assistant' approach falls flat quickly. The real value comes when the agent understands your decision-making patterns well enough to pre-filter and frame information the way you'd want it. Curious how long the training loop took before Jarvis started being genuinely useful versus just another thing to manage.

Fascinating architecture, Kyle. But it’s hard to ignore the Sorcerer’s Apprentice paradox at play here. You’ve successfully taught the brooms to carry the water, but from a D&O perspective, Jarvis isn't just an assistant—it’s a permanent, searchable record of executive intent. When leadership meetings consist of more agents than humans, you’ve effectively digitized the smoking gun for future securities litigation. With the 4.9x surge in agentic scheming documented this year (per CLTR), the risk isn't a software glitch; it’s an autonomous, machine-speed disclosure trap. The efficiency is impressive, but if the brooms start talking to each other without a human "Stop spell" integrated into the liability tower, the room floods long before you can check the dashboard.

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I love this. We're living in wild times. It's cool to see how everyone approaches using AI differently and how flexible the systems are to adapt to anyone's workflows and style

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