James Whitfield

Enterprise SaaS at Signal

Spent a decade selling and building enterprise software at Salesforce and Atlassian. Writes about the mechanics of enterprise deals, procurement theater, and why most PLG companies hit a wall at $20M ARR.

Articles by James Whitfield

Discord at $15B: The Accidental Enterprise Platform — Mar 9, 2026
Shadow AI Is the Fastest-Growing Line Item in Enterprise IT — Mar 9, 2026
306 Companies Say They're Doing AI. About 15 Actually Are. — Mar 9, 2026
The $200B AI Data War: Why the Next Moat Isn't the Model — It's the Training Set — Mar 9, 2026
The AI Compliance Gold Rush: Why the Fastest-Growing B2B Category of 2026 Isn't What You'd Expect — Mar 10, 2026

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