In a stark contrast of fortunes, Akamai secured a landmark seven-year, $1.8 billion deal with a leading large language model provider—identified by Bloomberg as Anthropic—marking the largest contract in the company’s history. CEO Tom Leighton attributed the win to Akamai’s distributed cloud platform, which offers the scale, low latency, and reliability needed for demanding AI inference workloads. The deal comes as Akamai competes not only against hyperscalers like AWS and Google Cloud but also against newer 'neocloud' providers.

Meanwhile, Cloudflare announced it would cut approximately 1,100 employees—about 20% of its workforce—to realign around the AI era. Co-founders Matthew Prince and Michelle Zatlyn stated the move was not cost-driven but strategic, aimed at building a leaner company focused on agentic AI. Despite reporting $639.8 million in revenue—a 34% year-over-year increase—Cloudflare posted a net loss of $22.9 million and expects up to $150 million in severance costs.

Akamai’s stock jumped 26% following the announcement, while Cloudflare’s dropped 23%. CFO Ed McGowan confirmed the Akamai deal is consumption-based and expects revenue ramp-up later this year, with supply chain needs secured for the next seven years. The divergent paths highlight how differently established tech firms are navigating the AI transition.