DK Street Journal

Toast Is the Only One of Eight Cloud Vendors Whose Gross Margin Went Up Last Quarter

Hypothesis Opus 5 · Research Opus 5 · Writing Opus 5 · Prompt v1.4

Eight companies that sell the plumbing of the cloud — networks, databases, monitoring, identity — have added about 12% as a group in a month, and at four of them revenue genuinely is accelerating. Cloudflare grew 36% last quarter, its fourth straight quarter of faster growth. What accelerated alongside it was the cost of delivering the service: Cloudflare's gross margin fell 317 basis points from a year earlier, Datadog's slipped both year over year and sequentially, and ServiceNow's dropped almost seven points. Toast, which sells point-of-sale systems to restaurants, is the only one of the eight whose gross margin widened.

The month is thinner than it looks. Strip each name's two best sessions and the group's gain becomes -1.6%, with six of the eight negative. The largest single day was a rotation out of chip stocks, not an earnings print. And all eight are dearer against gross profit than in early May — about 51% dearer on average.

NETAKAMDDOGNOWSNOWOKTAMDBTOSTHUBSMNDYDOCUBILLPANWRBRKTEAMTWLOZSCRMWDAY
TickerCompanySegmentTrend · 13mo30D1Y
The subject · what this brief is about
NETCloudflareNetwork & Application Delivery🟢 Cont. Bull+12.7%+51.7%
AKAMAkamai TechnologiesNetwork & Application Delivery🟢 Cont. Bull−0.2%+63.2%
DDOGDatadogData & Analytics Platforms🌱 Emerging Bull−5.1%+93.6%
NOWServiceNowSpecialized Enterprise Solutions🔴 Cont. Bear+12.9%−33.7%
SNOWSnowflakeData & Analytics Platforms🟢 Cont. Bull+21.6%+68.2%
OKTAOktaIdentity & Access Management🌱 Emerging Bull−3.5%+56.8%
MDBMongoDBData Management & Analytics🟢 Cont. Bull+36.8%+94.9%
TOSTToastPoint-of-Sale & Hospitality🔴 Cont. Bear+11.1%−19.3%
Compared against · context, not the story
HUBSHubSpotCustomer Experience & CRM🔴 Cont. Bear−6.9%−52.0%
MNDYmonday.comOther🔴 Cont. Bear+8.1%−53.6%
DOCUDocuSignSpecialized Enterprise Solutions🔴 Cont. Bear+14.7%−16.3%
BILLBill.comFintech & Digital Finance⚠️ Emerging Bear+7.3%+16.4%
PANWPalo Alto NetworksCybersecurity & Threat Protection🌱 Emerging Bull+7.8%+113.3%
RBRKRubrikOther🌱 Emerging Bull+29.2%+17.8%
TEAMAtlassianDeveloper Tools & DevOps🔴 Cont. Bear+64.2%−6.4%
TWLOTwilioCommunications & Messaging Platforms🟢 Cont. Bull+11.4%+117.6%
ZSZscalerAI & Data Intelligence🔴 Cont. Bear+23.1%−33.4%
CRMSalesforceCustomer Experience & CRM🔴 Cont. Bear+9.9%−21.3%
WDAYWorkdayEnterprise Resource Planning🔴 Cont. Bear+29.2%−18.0%

12-month price & trend

NET
Cloudflare
307
−8.77 (−2.78%)
vs. prior close
Price20d50d150d
NET 12-month price
Network & Application Delivery
AKAM
Akamai Technologies
123
−2.10 (−1.68%)
vs. prior close
Price20d50d150d
AKAM 12-month price
Network & Application Delivery
DDOG
Datadog
250
−5.59 (−2.19%)
vs. prior close
Price20d50d150d
DDOG 12-month price
Data & Analytics Platforms
TickerMkt capP/EP/E fwdP/SP/S fwdP/GPP/GP fwdEV/EBITDAFCF yld
NET$109.0Bn/m256.6x43.4x38.8x59.8x53.5x0.3%
AKAM$17.9B43.3x18.4x4.1x4.0x7.3x7.0x20.0x3.5%
DDOG$88.0B497.4x101.3x22.2x20.1x27.9x25.3x337.6x1.3%
NOW
ServiceNow
118
−5.76 (−4.65%)
vs. prior close
Price20d50d150d
NOW 12-month price
Specialized Enterprise Solutions
SNOW
Snowflake
334
+4.58 (+1.39%)
vs. prior close
Price20d50d150d
SNOW 12-month price
Data & Analytics Platforms
OKTA
Okta
143
−4.19 (−2.84%)
vs. prior close
Price20d50d150d
OKTA 12-month price
Identity & Access Management
TickerMkt capP/EP/E fwdP/SP/S fwdP/GPP/GP fwdEV/EBITDAFCF yld
NOW$121.7B73.1x28.9x8.3x7.5x11.0x10.0x36.6x3.8%
SNOW$114.4Bn/m170.9x22.7x18.8x33.9x27.9xn/m1.0%
OKTA$23.8B102.3x37.2x7.9x7.4x10.3x9.6x65.1x3.8%
MDB
MongoDB
442
−17.86 (−3.88%)
vs. prior close
Price20d50d150d
MDB 12-month price
Data Management & Analytics
TOST
Toast
34.28
−0.47 (−1.35%)
vs. prior close
Price20d50d150d
TOST 12-month price
Point-of-Sale & Hospitality
HUBS
HubSpot
215
−8.97 (−4.00%)
vs. prior close
Price20d50d150d
HUBS 12-month price
Customer Experience & CRM
TickerMkt capP/EP/E fwdP/SP/S fwdP/GPP/GP fwdEV/EBITDAFCF yld
MDB$35.3Bn/m71.7x13.6x11.9x18.8x16.5x1.7%
TOST$19.9B41.3x24.8x2.9x2.7x11.0x10.0x35.1x2.9%
HUBS$11.5B79.1x17.0x3.3x3.1x4.0x3.7x37.9x6.7%
MNDY
monday.com
82.99
−4.53 (−5.18%)
vs. prior close
Price20d50d150d
MNDY 12-month price
Other
DOCU
DocuSign
60.01
−2.03 (−3.27%)
vs. prior close
Price20d50d150d
DOCU 12-month price
Specialized Enterprise Solutions
BILL
Bill.com
48.50
−1.28 (−2.57%)
vs. prior close
Price20d50d150d
BILL 12-month price
Fintech & Digital Finance
TickerMkt capP/EP/E fwdP/SP/S fwdP/GPP/GP fwdEV/EBITDAFCF yld
MNDY$4.7B39.8x20.3x3.6x3.2x4.1x3.6x51.1x6.4%
DOCU$11.5B38.4x13.3x3.5x3.3x4.4x4.1x17.2x9.7%
BILL$5.0Bn/m14.8x3.1x2.7x3.8x3.3x42.8x7.7%
PANW
Palo Alto Networks
376
−8.51 (−2.21%)
vs. prior close
Price20d50d150d
PANW 12-month price
Cybersecurity & Threat Protection
RBRK
Rubrik
101
−1.21 (−1.18%)
vs. prior close
Price20d50d150d
RBRK 12-month price
Other
TEAM
Atlassian
158
−3.88 (−2.39%)
vs. prior close
Price20d50d150d
TEAM 12-month price
Developer Tools & DevOps
TickerMkt capP/EP/E fwdP/SP/S fwdP/GPP/GP fwdEV/EBITDAFCF yld
PANW$313.2B322.9x93.4x29.5x22.6x41.0x31.5x137.3x1.4%
RBRK$21.0Bn/m329.5x14.8x12.8x18.3x15.9xn/m1.5%
TEAM$42.6Bn/m26.7x6.5x5.8x7.6x6.8x282.1x3.1%
TWLO
Twilio
229
−9.59 (−4.03%)
vs. prior close
Price20d50d150d
TWLO 12-month price
Communications & Messaging Platforms
ZS
Zscaler
184
+0.84 (+0.46%)
vs. prior close
Price20d50d150d
ZS 12-month price
AI & Data Intelligence
CRM
Salesforce
191
−5.24 (−2.67%)
vs. prior close
Price20d50d150d
CRM 12-month price
Customer Experience & CRM
TickerMkt capP/EP/E fwdP/SP/S fwdP/GPP/GP fwdEV/EBITDAFCF yld
TWLO$36.2B31.7x41.7x6.5x6.2x13.4x12.8x99.3x3.1%
ZS$29.7Bn/m40.1x9.4x7.6x12.2x9.9x251.1x3.2%
CRM$160.7B22.6x13.9x3.8x3.5x4.8x4.5x13.8x9.1%
WDAY
Workday
190
−8.47 (−4.26%)
vs. prior close
Price20d50d150d
WDAY 12-month price
Enterprise Resource Planning
TickerMkt capP/EP/E fwdP/SP/S fwdP/GPP/GP fwdEV/EBITDAFCF yld
WDAY$47.1B55.8x16.7x4.8x4.4x6.3x5.8x30.0x6.3%

Consensus projections

TickerFY2026EFY2027EFY2028E
NETRevenue+31.0%+27.9%+27.4%
EPS+31.0%+32.8%+38.3%
AKAMRevenue+7.4%+11.0%+10.4%
EPS−5.0%+6.5%+11.1%
DDOGRevenue+28.9%+21.5%+23.5%
EPS+20.9%+17.3%+23.1%
NOWRevenue+22.4%+18.7%+18.6%
EPS+17.1%+23.2%+21.4%
SNOWRevenue+29.4%+30.9%+25.7%
EPS+72.3%+59.4%+41.1%
OKTARevenue+12.0%+10.0%+9.5%
EPS+24.3%+11.7%+10.8%
MDBRevenue+23.1%+21.6%+17.9%
EPS+59.1%+27.1%+19.6%
TOSTRevenue+21.7%+18.3%+17.4%
EPS+34.7%+24.7%+24.2%
HUBSRevenue+18.5%+14.9%+14.0%
EPS+37.2%+22.5%+18.5%
MNDYRevenue+19.8%+16.1%+16.1%
EPS+7.0%+21.4%+10.9%
DOCURevenue+8.4%+8.9%+7.6%
EPS+6.9%+19.5%+12.6%
BILLRevenue+13.2%+12.2%+12.0%
EPS+26.0%+27.2%+20.5%
PANWRevenue+24.3%+21.1%+14.1%
EPS+15.3%+9.0%+17.6%
RBRKRevenue+48.7%+28.4%+21.5%
EPS−90.5%−278.4%+106.3%
TEAMRevenue+24.7%+13.4%+15.9%
EPS+55.5%+10.5%+18.0%
TWLORevenue+16.0%+10.1%+10.4%
EPS+19.1%+16.3%+15.7%
ZSRevenue+25.2%+16.9%+16.7%
EPS+29.0%+11.2%+17.6%
CRMRevenue+9.3%+11.1%+9.4%
EPS+17.4%+20.2%+10.4%
WDAYRevenue+13.4%+11.8%+11.0%
EPS+26.5%+18.5%+17.3%

Forward fiscal years only. Blank means no analyst coverage for that year.

Between 22 July and 6 August, seven of these eight companies reported. The prints were, on the top line, better than the software industry's 2026 reputation would suggest. Cloudflare, which runs a global network selling denial-of-service protection, zero-trust access and edge computing to enterprises and developers, grew revenue 36% to $696.1m and raised full-year guidance to a range topping out at $2.870bn. That was its fourth consecutive quarter of acceleration. Dollar-based net revenue retention — what existing customers spend now versus a year ago — reached 120%, up six points on the year. Management says more than half the traffic crossing its network is now AI agents rather than people.

Datadog, which monitors cloud infrastructure and bills per host and per log ingested, also accelerated for a fourth straight quarter, to 35.6% and $1.121bn, its fastest sequential growth since 2022. ServiceNow, whose workflow software runs corporate IT and HR processes on a per-seat licence, reaccelerated to 24.0%, with current remaining performance obligations — contracted revenue due within a year — up 21.5% and artificial-intelligence contract value crossing $1bn.

The cost of serving AI

The same quarters show where the growth is being bought. Cloudflare's reported gross margin fell to 71.8% from 74.9%. Datadog's fell to 78.6% from 79.9%, and slipped sequentially too. ServiceNow's dropped to 70.7% from 77.5%, a 681-basis-point compression that took operating margin to 4.1% from 11.1%. Akamai, the original content-delivery network now rebuilding itself around security and cloud compute, is worse: revenue grew 5.4%, gross margin fell to 55.8%, and gross profit shrank 0.5% outright. Its shares fell after the print as profit contracted under build-out costs, with all existing graphics-processor capacity sold out. Third-quarter capital spending is guided at up to 46% of revenue, funded partly by a $3.5bn zero-coupon convertible and a suspended buyback.

Toast is the exception, and it is the exception in the direction that matters. Gross margin reached 27.0% against 25.3%, operating margin 8.0% against 5.2%, on revenue up 23.1% to $1.908bn. It added a record 9,500 net restaurant locations to roughly 180,000 and raised full-year guidance for recurring gross profit growth. Even its problem is instructive: hardware margin sits near -11% because AI demand has inflated memory-chip prices, and management expects a bigger hit in 2027 than 2026.

What the month actually priced

The group's 12.4% gain over the 18 sessions to 17 August does not survive inspection. Remove each company's two best days and the equal-weight return is -1.6%, with six of eight negative. ServiceNow's 14.5% month becomes -7.1%; Toast's 14.0% becomes -0.2%; Cloudflare's 10.6% becomes -1.7%; Datadog is down 3.4% before stripping and down 17.7% after.

The biggest day was not an earnings day. ServiceNow rose 15.9% on 28 July, six sessions after its own results, alongside Toast up 10.7%. That was the day money rotated out of chip stocks and into beaten-down software, with Salesforce and Workday moving in step; the Philadelphia Semiconductor Index had run more than 130% into a June high before investors decided the AI trade needed rebalancing. Datadog's best session, up 11.5% on 10 August, came four days after its print, on a wave of broker price-target increases.

The two moves that do survive the strip belong to the two companies that have published nothing. MongoDB, which sells the Atlas managed document database, is up 41.7% over the month, 23.8% ex its two best days — and has not held an earnings call since 28 May. Snowflake, whose data platform bills per credit of compute consumed, is up 24.0% and last reported on 27 May; its advance came with a sequence of price-target raises rather than new consumption data.

Dearer at every one

Measured against trailing gross profit, all eight are more expensive than in early May, by an average of 51%. Snowflake went from 15.7x to 33.9x. Datadog went from 17.0x to 27.9x, MongoDB from 11.7x to 18.8x, Cloudflare from 45.4x to 59.8x. Cloudflare is the dearest thing here on any measure: 53.5x forward gross profit and 257x forward earnings, against a quarterly net loss of $170.0m and a full-year restructuring charge lifted to $165m.

Okta, which sells single sign-on and identity management per seat, is the awkward case. Its multiple went from 6.0x to 10.3x trailing gross profit, a 72% expansion, while the business decelerated for a fourth straight quarter to 11.2% growth and consensus models 9.5% for the fiscal year ending January 2028. It has reported nothing since 28 May and fell 4.1% over the month. Its margins, at least, are going the right way: operating margin 7.3% against 5.7%.

The premium over application software has widened rather than closed. HubSpot, which sells marketing and sales software to mid-sized firms, trades near 4.4x gross profit; Monday.com, a work-tracking tool, near 3.2x. Both are down more than half over twelve months. Toast, at 11.0x against 10.5x in May, is the only member of the infrastructure group whose multiple has barely moved while its gross profit grew 32%.

The setup

Where it stands — Revenue is accelerating at four of these eight, gross margin is compressing at every AI-exposed one, and all are dearer than in May. Would confirm — Cloudflare or Datadog posting a sequential gross-margin gain on a reported basis next quarter. Would invalidate — Datadog's third quarter landing at the guided 28-29% growth or below as its largest AI customer cuts usage. Watch next — Snowflake and MongoDB report late August, their first income statements since May. Valuation — Group ranges from Akamai at 7.3x trailing gross profit to Cloudflare at 59.8x trailing and 53.5x forward.