Insights
August 17, 2026
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
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
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 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
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
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.