Series · 6 posts
Before the Budget Line
Most of my career has been selling things buyers had no budget for yet. These posts are about how that sale works and how it changes once the category is real.
- 01Selling AI to skeptical buyers (a field guide)Marketers, agency leads, pharma commercial teams — the buyers I sell to are smart, busy, and have seen 50 AI demos this quarter. Here's how I frame the conversation so th… Feb 11, 2026 7 min
- 02Anthropic just crossed $900B. The AI category sale is over.Anthropic is reportedly closing a $30B round at a $900B+ valuation. PwC is certifying 30,000 professionals on Claude. The Big Four have placed their bets. The enterprise… May 26, 2026 7 min
- 03The companies with the best AI on earth are hiring salespeople faster than SaaS is.At OpenAI and Anthropic, go-to-market is the single largest category of open roles, about one in five, ahead of research and engineering. The firms most able to automate… Jun 17, 2026 5 min
- 04Microsoft spent $2.5 billion to put its own engineers inside your customer's building.Microsoft launched Frontier Company on July 2 — a $2.5 billion unit staffing 6,000 engineers to embed inside customers and drag their AI from pilot to production. Most co… Jul 8, 2026 6 min
- 05I closed my best deal four timesThe whole AI-sales boom points at landing the customer — AI SDRs, PLG, ChatGPT ads, pilot-to-production. But once pricing moved to usage and outcomes, the vendor only ear… Jul 11, 2026 6 min
- 06Six technology shifts later, the same sales job keeps dyingBroadcast, digital, social, programmatic, data, AI — I've carried a quota through all six. Up close they look like six different disruptions. They're one pattern on repea… Jul 11, 2026 7 min
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