Microsoft coaches sales team to undercut OpenAI, Anthropic

Microsoft ↘ 0.44% is coaching its sales force on how to aggressively compete against Anthropic and OpenAI, highlighting weaknesses in their rival products, Bloomberg reported on Tuesday. The internal guidance marks a sharpening of the rivalry between Microsoft and the AI companies it has invested billions in over recent years.news.bloomberglaw+1

From Partner to Competitor

The sales coaching effort comes amid a broader strategic shift at Microsoft to reduce its dependence on external AI providers. Earlier this month, Bloomberg reported that Microsoft is replacing OpenAI and Anthropic models with its own internally built MAI models in products like Excel and Outlook, with tens of thousands of AI prompts now handled weekly by in-house technology. The company also recently deployed a 6,000-person organization dedicated to helping business customers adopt AI.bloomberg+3

The competitive posture reflects how Microsoft's relationship with OpenAI has evolved from a close partnership into something more adversarial. In April, the two companies dropped their exclusivity arrangement on AI models, and Microsoft has since accelerated development of its own foundation models under AI chief Mustafa Suleyman.youtube

A Three-Way Enterprise Battle

The enterprise AI market has become a three-way contest. OpenAI has been pushing into business customers, tripling its revenue to $5.7 billion in the first quarter of 2026 while burning $3.7 billion. Anthropic, valued at $380 billion, has been aggressively hiring talent from Microsoft, OpenAI, and Google Alphabet Inc. ↘ 3.61%. Both companies are competing directly with Microsoft's Copilot products for corporate spending.crn+2

Microsoft's decision to arm its sales team with competitive talking points against companies it simultaneously partners with underscores the tension at the heart of the AI industry's current chapter — where today's investors and collaborators are tomorrow's fiercest rivals.