Insights

September 21, 2026

An eval measures performance. A release gate decides what you can claim.

A benchmark measures how a system behaves. A release gate decides what you are allowed to say about it. They are different jobs, and conflating them is how a capability claim nobody can evidence ends up in a datasheet.

September 17, 2026

Everyone Tracks Renewals Now. The Number Is Still Wrong.

Renewal tracking got solved a decade ago. The 2026 problem is that the number attached to a tracked renewal is wrong, and no amount of reorganizing sales and CS fixes an input problem.

September 8, 2026

By the Time You Price It, the Meter Is Already Chosen

Google just put a compute meter on Gemini Notebook. The meter was not designed for Notebook. It was already in use elsewhere, and that is the part worth understanding.

August 17, 2026

In Three Market Expansions, the Product Was Never the Hard Part

Three market expansions where the product could do the job. What blocked it was different every time: the shape of the box, the story around it, or a portfolio boundary inside the company. A field guide to telling which one you are facing.

August 4, 2026

The AI Cost Stack Nobody Maps

Every AI feature adds recurring marginal cost, but roadmaps still get approved as if software COGS were zero. A map of the AI cost stack, and the three decisions it forces.

July 29, 2026

Your AI Roadmap Has a Portfolio Pricing Problem

AI features get priced one launch at a time, but buyers judge them as one portfolio against one budget. Why AI pricing is an architecture problem, and how to map it.

May 8, 2026

AI Features Are Easy to Ship. Harder to Price.

AI features create value, but monetizing them is harder than shipping them. Seat models come under pressure, packaging needs to map to value, and teams need instrumentation before the pricing anchor sets.

April 28, 2026

Pricing Is a Product Problem, Not a Finance Problem

At Cisco ISE, the monetization transformation grew annual bookings to $350M+. The price change was important. But the system around it—the usage tracking, the engineering infrastructure, the financial bridge model, the sales enablement—was what made it stick.

December 18, 2025

The Compounding Effect: Real-World Lessons from Scaling a Product

Only 3.5% of SaaS startups reach $20M ARR within ten years. Here's how ISE grew 5× through compounding improvements in monetization and retention.