Three companies that charge for software the way a utility charges for electricity — by the request, the server, the gigabyte — reported June quarters this month. Two of them grew at almost exactly the same rate. What separated them was a single customer.

The same top line, two outcomes

Datadog sells cloud monitoring and analytics to developers and operations teams, metered by host, by gigabyte of logs ingested and by custom metric. Revenue reached $1.12bn in the June quarter, up 35.6% and the fifth consecutive quarter of acceleration. Dollar-based net retention sits in the low 120s, and customers spending over $100,000 a year rose to 4,720 from 3,850, generating 91% of annual recurring revenue.

None of that mattered on 6 August. Management disclosed that its largest customer — a leading AI company running 17 Datadog products on a nine-figure contract, widely believed on Wall Street to be OpenAI though the company has never named it — renewed on reduced usage from the September quarter. Guidance for that quarter implies 28-29% growth, down from 36%. The shares lost 20.4% that day.

The fact buried underneath is more interesting than the hole. Datadog's non-AI revenue is now growing at a high-20s percentage rate, up from 18% a year earlier — five straight quarters of acceleration in the ordinary enterprise base. More than 750 customers are AI-native, 31 of them spending over $1m and eight over $10m. Neither Datadog nor Cloudflare publishes AI revenue as a share of the total, so no outsider can size the concentration precisely; that opacity is itself the risk consumption billing carries.

Cloudflare, which operates an edge network of security, content delivery and per-request serverless compute across 335-plus locations, beat consensus revenue by 4.6% at $696.1m, up 35.9% and a fourth straight acceleration. Net retention improved six points year on year to 120%. Remaining performance obligations — contracted revenue not yet recognized — reached $2.73bn, up 38%. Customers above $100,000 rose 27% to 4,698.

It was bought, though. Non-GAAP gross margin of 73.1% is 320 basis points below last year, as free network traffic grew faster than paid, and the company booked $165m of severance and restructuring alongside a 20% workforce reduction. Management is deliberately refusing the capital-expenditure arms race, holding network capex at 14-15% of revenue.

Akamai is a different company wearing the same label

Akamai, the original content-delivery carrier, embeds servers inside 4,400-plus internet service providers. Delivery revenue fell 6% to $396m last quarter and is guided to a mid-single-digit decline for the year. Security grew 10% to $604m; the new cloud infrastructure line grew 39% to $99m. Total revenue rose 5.4% — but trailing gross profit fell 0.5% and operating income dropped 47%, with capital spending at 32% of revenue heading toward roughly 40% for the year, funded by convertibles now totaling about $7.6bn, with the buyback paused. The shares fell almost 7% after results.

The offset is $2.8bn of signed multi-year compute contracts, including an $1.8bn seven-year commitment from Anthropic — the largest deal in Akamai's history — and a $600m robotics deal. Revenue from them starts in the fourth quarter of 2026 at roughly $20-25m. Anthropic itself told investors its annualized revenue passed $65bn in July, from $9bn at the end of 2025, so the counterparty is not the question. Timing is.

What a dollar of gross profit costs

Gross margins here run 78.6%, 71.8% and 55.8%, so revenue multiples flatter Akamai and punish nobody usefully; price against gross profit is the comparable lens. Cloudflare trades at 56.8x trailing gross profit, up from roughly 43x in mid-May — a third of its 41% three-month gain is re-rating, not compounding. Datadog is at 26.4x, essentially where it stood in mid-May, so its quieter 8.5% three-month gain was earned; measured from early May, when it was near 17.7x, it remains about 49% dearer. Akamai has fallen to 6.7x from 8.4x, and its 16.9x forward earnings sit on consensus 2026 earnings per share of $6.69 — 5% below 2025.

The charts flatter all three. Datadog's 50-day average has held above its 200-day since 21 May and Cloudflare's since 5 May, while Akamai's crossed lower on 2 July and has not recovered. But over the month to 19 August, Datadog fell 11.3% and Akamai 8.4% as Cloudflare rose 7.1% — and strip Cloudflare's two best sessions and that becomes roughly -4.8%. On 18 and 19 August all three fell, as the 30-year Treasury yield touched about 5.33%, its highest since 2007. Long-duration software was sold, not bought.

The setup

Where it stands — Two usage-billed businesses grew alike last quarter and now carry multiples two-to-one apart; the third is de-rating on shrinking gross profit. Would confirm — Datadog's September quarter landing above the 28-29% guide with net retention still in the low 120s. Would invalidate — Cloudflare's net retention slipping below 118% or non-GAAP gross margin resuming its decline from 73.1%. Watch next — Akamai's fourth-quarter report, the first to include revenue from the $1.8bn Anthropic commitment. Valuation — Price to trailing gross profit: Cloudflare 56.8x (49.8x forward), Datadog 26.4x (23.9x), Akamai 6.7x.