DK Street Journal

Cloud-Software Stocks Rally as Bookings Reaccelerate, Not Just Cheap Valuations

Hypothesis Opus 5 · Research Sonnet 5 · Writing Sonnet 5 · Prompt v1.1

A group of eight cloud-infrastructure software companies gained an average 30% over the past year, and the group's last holdout, ServiceNow, just posted a bookings beat that ended its own multi-quarter slide — but three of the biggest gainers, Datadog, Snowflake and Okta, have already re-rated back to stretched valuations, leaving less room from today's price than the year-long chart suggests.

NETAKAMDDOGMDBNOWSNOWOKTATOST
TickerCompanySegmentTrend30D1Y
NETCloudflareNetwork & Application Delivery🟢 Cont. Bull+12.7%+33.6%
AKAMAkamai TechnologiesNetwork & Application Delivery🟢 Cont. Bull+2.2%+52.6%
DDOGDatadogData & Analytics Platforms🟢 Cont. Bull+4.9%+92.6%
MDBMongoDBData Management & Analytics🟢 Cont. Bull−5.7%+49.0%
NOWServiceNowSpecialized Enterprise Solutions🔴 Cont. Bear+3.1%−39.7%
SNOWSnowflakeData & Analytics Platforms🟢 Cont. Bull+11.9%+40.7%
OKTAOktaIdentity & Access Management🌱 Emerging Bull−2.1%+48.9%
TOSTToastPoint-of-Sale & Hospitality🔴 Cont. Bear+9.5%−34.5%

12-month price & trend

NET
Cloudflare
279
−4.41 (−1.56%)
vs. prior close
Price20d50d150d
NET 12-month price
Network & Application Delivery
AKAM
Akamai Technologies
115
+1.43 (+1.26%)
vs. prior close
Price20d50d150d
AKAM 12-month price
Network & Application Delivery
DDOG
Datadog
268
−0.59 (−0.22%)
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$98.9Bn/m232.7x42.5x35.2x58.6x48.5x736.1x0.4%
AKAM$16.7B38.3x17.2x3.9x3.7x6.9x6.6x16.6x4.6%
DDOG$95.4B696.4x110.7x26.0x21.9x32.7x27.5x421.1x1.1%
MDB
MongoDB
337
+11.60 (+3.56%)
vs. prior close
Price20d50d150d
MDB 12-month price
Data Management & Analytics
NOW
ServiceNow
111
+1.16 (+1.05%)
vs. prior close
Price20d50d150d
NOW 12-month price
Specialized Enterprise Solutions
SNOW
Snowflake
293
−4.82 (−1.62%)
vs. prior close
Price20d50d150d
SNOW 12-month price
Data & Analytics Platforms
TickerMkt capP/EP/E fwdP/SP/S fwdP/GPP/GP fwdEV/EBITDAFCF yld
MDB$27.1Bn/m55.1x10.4x9.2x14.5x12.8x2.2%
NOW$115.0B69.1x27.3x7.8x7.1x10.4x9.5x34.7x4.0%
SNOW$101.7Bn/m151.8x20.2x16.7x30.1x24.9xn/m1.2%
OKTA
Okta
145
+3.54 (+2.49%)
vs. prior close
Price20d50d150d
OKTA 12-month price
Identity & Access Management
TOST
Toast
32.27
−0.58 (−1.77%)
vs. prior close
Price20d50d150d
TOST 12-month price
Point-of-Sale & Hospitality
TickerMkt capP/EP/E fwdP/SP/S fwdP/GPP/GP fwdEV/EBITDAFCF yld
OKTA$24.2B103.9x37.8x8.1x7.6x10.5x9.8x66.2x3.7%
TOST$18.7B46.1x24.2x2.9x2.5x10.9x9.4x37.3x3.5%

Valuation & fundamentals

Consensus projections

TickerFY2026EFY2027EFY2028E
NETRevenue+31.0%+27.9%+27.4%
EPS+31.1%+32.5%+38.7%
AKAMRevenue+7.4%+10.9%+10.4%
EPS−4.9%+6.7%+10.7%
DDOGRevenue+28.3%+21.3%+23.9%
EPS+19.9%+17.8%+22.9%
MDBRevenue+23.1%+21.6%+17.9%
EPS+59.1%+27.1%+19.6%
NOWRevenue+22.4%+18.7%+18.5%
EPS+17.1%+23.2%+21.5%
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%
TOSTRevenue+20.4%+18.0%+16.8%
EPS+30.1%+24.9%+29.7%

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

In early 2026, investors punished enterprise software broadly on fear that AI agents would let companies do more with fewer paid software seats, sending a widely tracked software index down more than 21% and, for the first time ever, below the S&P 500's valuation. That fear didn't materialize for eight companies that supply the internet's underlying infrastructure — content delivery, cloud databases, identity checks and system monitoring — which have gained an average 30% over the trailing year. The group's last holdout, ServiceNow, which sells workflow-automation software large enterprises use to manage IT tickets and other back-office processes, just reported subscription revenue up 24.5% and a bookings measure (contracted-but-not-yet-billed revenue) up more than 21%, both beating its own guidance, and raised its full-year outlook. The trend model tracking its stock moved from deeply bearish to mildly bearish within three trading days of that report — a sign the rally's final laggard is turning on new bookings, not just a bounce in a beaten-down stock.

Broad participation, not two names carrying it. Six of the eight members — Datadog (+92.6% over the year), MongoDB (+49.0%), Akamai (+52.6%), Okta (+45.3%), Snowflake (+40.7%) and Cloudflare (+33.6%) — are all up double digits over the trailing twelve months; only ServiceNow (-39.7%) and Toast (-34.5%) are negative for the year. But those two laggards are now the fastest-moving names over the past 90 days (ServiceNow +20.9%, Toast +13.1%), meaning the group's weakest members are inflecting hardest, not lagging behind a two-name rally. As of July 31, trend patterns confirm the breadth: Cloudflare, Datadog, Okta and Snowflake trade above both their short- and long-term moving averages in a strong uptrend; Akamai, MongoDB and Toast sit in milder uptrends; only ServiceNow remains in a downtrend, though a less severe one than a week earlier.

Does the business support the move? Mostly, yes. Datadog, whose software watches over the health of clients' cloud servers and applications, posted its first-ever $1 billion revenue quarter, growth of 32%, and raised full-year guidance by $240 million after a single quarter, adding customers paying more than $100,000 a year at a 21% clip. Snowflake, which rents out cloud storage and analytics tools that let companies query massive datasets, raised its full fiscal-year revenue-growth guidance from 27% to 31%, helped by an AI coding tool, Cortex Code, that gained more customers than management had modeled. Okta, which verifies employee and customer logins for other companies' software, saw a retention metric inflect for the first time in years, from 106% to 107% of prior-year revenue retained, in a quarter management linked partly to new AI-agent-identity demand. CONFIRMS: the earnings evidence supports the price move for these three, and for ServiceNow above.

The picture is more mixed for the rest. Cloudflare, which runs a global network delivering websites, blocking cyberattacks and offering a computing platform called Workers, grew revenue 28% to $738 million last quarter and guided to more than $5 billion in revenue before 2028, but the stock also fell 24% on its own earnings day in May after the company cut roughly a fifth of its staff to reshape its cost structure around AI — a genuinely two-sided quarter. MongoDB, whose Atlas cloud database is used by developers building AI applications, grew Atlas revenue 29% and saw vector-search adoption nearly double, even as total-company revenue growth is guided to slow to 16%-18% next fiscal year — a real divergence between an exciting AI-adjacent metric and slowing total growth (INCONCLUSIVE). Akamai, the original content-delivery-network operator now pivoting toward security and cloud computing, signed a $1.8 billion, seven-year cloud contract with AI company Anthropic — its largest customer deal in 28 years — but that new business is still under 9% of revenue while its legacy delivery business keeps shrinking about 7% a year. Toast, which sells point-of-sale and payment software to restaurants, added 7,000 net new locations last quarter and raised full-year profit guidance, even as it was one of the year's two decliners.

Does the valuation justify it? Increasingly, no, for the biggest gainers. Datadog's trailing price-to-sales ratio nearly doubled in three months, from 13.6x to 24.3x; Okta's rose from 4.6x to 8.0x while its revenue grows only 9%-11% a year; Snowflake's climbed from 10.5x to 18.6x. That is CONTRADICTS territory — the re-rating from depressed multiples that started this move has largely already happened for these three. ServiceNow's price-to-sales ratio, by contrast, rose a milder 16% (6.7x to 7.8x) even after its earnings beat, and Toast's trailing price-to-earnings ratio actually fell, from 51.8x to 46.2x, because its profit grew faster than its stock — both still look like unwound de-rates with more room, a genuine CONFIRMS for the hypothesis's question about what's left from current prices.

The setup

Where it stands — Six of eight members show earnings-confirmed growth and bullish trend patterns; three of the biggest gainers already re-rated to stretched multiples. Would confirm — ServiceNow's next-quarter bookings growth holds above 20% and Okta's retention metric climbs past 107%. Would invalidate — Datadog, Snowflake or Okta's price-to-sales ratio retraces most of its 90-day gain without a matching growth slowdown to explain it. Watch next — ServiceNow, Datadog, Snowflake and Okta report fiscal third-quarter results between late September and December 2026. Valuation — Datadog trades at 24.3x trailing sales, up from 13.6x three months ago; ServiceNow at 7.8x, up a milder 16% over the same span.