Akamai Technologies issues warrant to Anthropic for 5% of common stock in massive cloud deal

Akamai Technologies just handed Anthropic the keys to a potentially enormous equity stake, issuing a warrant that lets the AI company purchase up to 5% of Akamai’s common stock. The catch: Anthropic has to spend billions on Akamai’s cloud services to fully unlock it.

The warrant is part of an $11.6 billion deal spanning seven years, announced on September 24, in which Akamai will provide cloud infrastructure to support Anthropic’s growing AI workload demands. Combined with a previous $1.8 billion contract announced in May, the total potential value of the relationship sits at roughly $20 billion.

How the equity piece works

Akamai structured the warrant around non-voting convertible Series B Preferred Stock, representing approximately 7.7 million shares of common stock. The exercise price is set at $111.33 per share.

About 2% of Akamai’s common stock vests immediately upon the $11.6 billion commitment. The remaining 3% vests incrementally as Anthropic spends up to an additional $9 billion on Akamai’s services over the contract’s duration.

The “non-voting” designation matters too. Anthropic can benefit financially from Akamai’s stock appreciation without gaining any boardroom influence. Akamai keeps control of its corporate governance while still offering a meaningful financial incentive to its largest client.

The bigger picture: $20 billion in combined contracts

Anthropic will use Akamai Cloud specifically for scaling CPU workloads, with revenue recognition kicking in as capacity gets activated.

For Akamai, a company historically known for content delivery networks and cybersecurity, landing a deal of this magnitude represents a serious pivot toward AI infrastructure.

What this means for Akamai’s competitive position

Akamai has historically competed in a different weight class than the hyperscale cloud giants. Amazon Web Services, Microsoft Azure, and Google Cloud dominate enterprise cloud spending, and all three have their own AI partnerships and internal AI efforts. AWS, notably, has invested billions into Anthropic directly.

Akamai’s annual revenue has historically hovered in the low single-digit billions, so a seven-year deal worth $11.6 billion, with potential upside to $20 billion, represents a transformational shift.

If Anthropic fully vests and exercises its 5% stake at $111.33 per share, that represents roughly $857 million in potential equity value at the exercise price alone.

For Akamai shareholders, the dilution is the obvious trade-off. Issuing up to 7.7 million new shares to a single customer is not trivial. But the argument from Akamai’s perspective is straightforward: 5% dilution is a reasonable price for locking in a customer that could eventually account for a significant portion of total revenue.