AnalysisBusinessAugust 26, 2026

Podcast: How OpenAI's slow enterprise response lost deals to Microsoft Copilot

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Aliisa Rosenthal, who joined OpenAI at ~$2M revenue, recounts that nine months after she requested enterprise features, OpenAI shipped them—but by then most prospects had bought Microsoft Copilot. The podcast explores the AI buyer's journey and enterprise sales dynamics.

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