Datadog, Inc. DDOG
Datadog remains a hold after the recent pullback to $233.52, as the stock still trades at 469.67x P/E and 20.96x P/S — a 1307.49% premium to the peer median P/E of 33.37x. FY2025 revenue grew 27.68% to $3.43B with a 29.19% FCF margin generating $1.0B in free cash flow, but GAAP operating income swung back to -$44.4M and diluted EPS fell to $0.30 from $0.51, a -41.18% decline.
Persistent heavy insider selling — net -$966.9M over 24 months — and a Seeking Alpha report flagging a large customer usage cut add fundamental risk, while the smart money score of 0.0743 as of the quarter ended 2026-06-30 shows only modest institutional conviction. The combination of strong top-line momentum and deteriorating profitability at an extreme valuation keeps the risk/reward balanced but unappealing.
What could go wrong
- Valuation compression. At 469.67x P/E and 318.95x EV/EBITDA versus peer medians of 33.37x and 24.50x, any growth deceleration could trigger a sharp de-rating.
- Customer concentration. A Seeking Alpha report (2026-08-18) flags that Datadog's largest customer has reduced usage, raising concerns about future growth durability.
- Margin deterioration. FY2025 operating margin of -1.29% worsened from +2.02% in FY2024, and EPS declined -41.18% year-over-year despite 27.68% revenue growth.
- Persistent insider selling. Over 24 months, insiders net sold 4,884,522 shares for -$966.9M, with continued sales by Jacobson Matthew on 2026-08-13 and 2026-08-14.
What would change my mind
Where this comes from: peer_relative composite · FMP FY2025 + derived_metrics · FMP FY2025/FY2024 + derived_metrics · insider summary. Orin's read on DDOG; not advice.
Twelve months actual closes to 2026-09-23 · actual filings
50-day average 200-day average · volume below
On file
All DDOG filingsLargest holders · 13F Q2 2026
Money flow| Filer | Position | Of fund |
|---|---|---|
| Vanguard Capital Management | $5.6B | 0.1% of fund |
| Fmr | $5.1B | 0.2% of fund |
| Vanguard Portfolio Management | $4.6B | 0.2% of fund |
| State Street | $3.8B | 0.1% of fund |
| Invesco | $3.4B | 0.3% of fund |
| Price T Rowe Associates /Md/ | $2.8B | 0.3% of fund |
117 filers · quarter ended Q2 2026 · positions, not flows
Insiders, last 24 months: 1112 Form 4 filings, net −$1.1B. Of the 50 on hand, 0 were open-market purchases and 44 sales— the rest are grants, option exercises and tax withholding.
Ask Orin about DDOG
Orin answers questions about DDOG from its filings, transcripts and numbers — with the source behind every claim. Your own desk starts with 3 free days, card required.
Start 3 free days →Where it trades
| Metric | Now | Own median | Sector |
|---|---|---|---|
| EV/EBITDA | 343.2× | — | — |
| P/S | 22.57× | 17.90× | — |
| P/B | 20.4× | 17.7× | — |
Its P/E sits 80th percentile of its own last 5 years (+0.67σ from its own mean).
28.3%
free-cash-flow growth every year for 10 years, discounted at 10%, is what today’s price implies — starting from $1.0B of trailing free cash flow. It is an assumption the market is making, not a forecast Orin is making.
What Wall Street published
$274
$158 – $320 · +10% against today's price
- 40 buy or overweight
- 7 hold
- 1 underweight or sell
The analysts’ consensus and their own ratings, not Orin’s. A target is a twelve-month opinion published by the firm that wrote it.
Against the companies it is compared to
| Company | Market cap | P/E | EV/EBITDA | Gross | Net | ROE |
|---|---|---|---|---|---|---|
| DDOGDatadog, Inc. | $90B | — | 343.2× | 79.5% | 4.5% | 5% |
| ADSKAutodesk, Inc. | $46B | 28.0× | 19.7× | 91.2% | 21.1% | 53% |
| CRWVCoreWeave, Inc. Class A Common Stock | $47B | — | 36.3× | 67.4% | -25.4% | -45% |
| FICOFair Isaac Corporation | $19B | 25.3× | 19.2× | 85.1% | 34.1% | -33% |
| NXPINXP Semiconductors N.V. | $59B | 20.0× | 13.7× | 55.9% | 22.6% | 28% |
| STXSeagate Technology Holdings plc | $207B | 63.5× | 49.2× | 45.6% | 26.1% | 348% |
| WDAYWorkday, Inc. | $50B | 38.9× | 32.1× | 75.8% | 12.3% | 17% |
| WDCWestern Digital Corporation | $163B | 17.4× | 18.7× | 48.9% | 72.9% | 119% |
The median is of the 6 peers listed above and nothing else — check it against the column. The peer set is the vendor’s, so a company can appear here that a person would not have chosen.
What it has traded at
What its sector has traded at
Two scales, drawn separately on purpose: a sector median and one company’s multiple are not the same number and putting them on one axis invites a comparison neither series supports.
Discounted cash flow
| Model | Fair value | Against | Computed |
|---|---|---|---|
| Standard DCF | $11 | $228.01 · −95% | 2026-06-10 |
| Levered DCF | $53 | $228.01 · −77% | 2026-06-10 |
The vendor’s intrinsic-value models. Treat them as a low-growth anchor — for a fast grower the market routinely pays well above a DCF. These were computed against the price in the “against” column, not today’s.
Every estimate on one scale
The vertical rule is the current price. Ranges and point estimates are the backend’s, published as they were calculated; an arrow means the estimate sits beyond this scale, and its number is on the right.