Line of Sight
For operators building and commercializing AI products.
What This Is
Most AI products fail to monetize. Not because the product is wrong, but because the commercial system underneath it was never built.
Line of Sight breaks down how to price AI products, build distribution, structure partnerships, and design the revenue architecture that turns a working product into a durable business.
Who It Is For
Founders and operators commercializing AI products. GTM leaders building on top of AI infrastructure. Corp dev and partnerships executives navigating the AI platform shift. Senior operators who need frameworks, not opinions.
If your job is to turn AI capability into revenue, you are in the right place.
If you are looking for AI thought leadership or general commentary, you are not.
Readers include operators and leaders at Anthropic, Meta, and Google.
What You Will Read
AI Pricing and Packaging. Token economics, cost modeling, and price architecture that survives when provider costs shift.
Distribution Architecture. How the fastest-growing AI companies build distribution into the product instead of bolting it on after launch.
Operator Frameworks. Build, Buy, or Partner decisions. Partner P&L systems. Cohort analysis as a forward signal. Tools built for operators, not consultants.
Commercial Intelligence. S-1 teardowns, market structure shifts, and the strategic moves that separate durable AI companies from ones that stall.
Free vs. Paid
Free posts deliver the core insight in under ten minutes.
Paid subscribers get the working model. Token Waterfall financial models, operator playbooks, and strategy briefs built to influence real pricing, distribution, and partnership decisions.
Every premium post is built to earn back the time you spend reading it many times over.
About Kyle Kelly
Nearly two decades building commercial systems at Amazon, Zappos, Aurora Solar, and a set of 0 to 1 companies where I carried the P&L. At Aurora, I ran the financing ecosystem as a full P&L in a $1B+ distributed energy market, where mismodeling cost structure by a few basis points killed deals.
The same dynamic is playing out in AI right now, at ten times the clock speed.
I write Line of Sight to help operators close the gap between AI capability and commercial architecture. Not as an observer. As an operator.
I also run WorkPlay Partners, an AI-native fractional executive practice taking on CCO, COO, and GM engagements with technology companies in the AI era. If you want operator help commercializing an AI product, that work lives at workplay.partners.
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