Compare · Technology
Cloudflare vs. Datadog: how they make money
The same facts for both companies, in the same order, from each company's own page and filings. This is not a ranking and says nothing about which share to own.
Each company in 5 points
Cloudflare
1 · What it sells
Cloudflare runs a network in more than 330 cities that protects and speeds up websites, apps and company networks, with $2,167.9 million of revenue in FY2025.
Sources and detail on the Cloudflare page2 · Who pays it
Cloudflare does not split revenue by type of customer, but by billing address in FY2025 the US paid 49%, Europe, the Middle East and Africa 28%, Asia Pacific 15% and other regions 8%, and no customer accounted for more than one-tenth of revenue.
Sources and detail on the Cloudflare page3 · What it keeps from $100
Of every $100 that came in during FY2025, including $131.2 million of interest income, costs were $104.4, so Cloudflare lost $4.4; its operating loss was $207.2 million.
Sources and detail on the Cloudflare page4 · Where the operating profit comes from
Cloudflare reports one segment and no profit by product; in FY2025 gross profit was $1,615.4 million, but sales, research and administration costs of $1,822.6 million left an operating loss of $207.2 million.
Sources and detail on the Cloudflare page5 · The one thing to watch
In Q3 FY2026 Cloudflare reported a GAAP operating loss of $67.9 million and non-GAAP operating income of $137.1 million, a gap mostly made up of $174.1 million of stock-based pay and related payroll tax.
Sources and detail on the Cloudflare page
Datadog
1 · What it sells
Datadog sells cloud software that watches companies' apps, servers and data for problems and attacks, with revenue of $3,427.2 million in FY2025.
Sources and detail on the Datadog page2 · Who pays it
Datadog does not split revenue by type of customer, but by billing address in FY2025 the US paid 67.7%, the rest of North America 3.3% and customers outside North America 29.0%, and it discloses no customer's share of revenue.
Sources and detail on the Datadog page3 · What it keeps from $100
Of every $100 that came in during FY2025, Datadog kept $3.0 as net income, which came from $182.5 million of interest and other income because its operations lost $44.4 million.
Sources and detail on the Datadog page4 · Where the operating profit comes from
Datadog reports one segment and no profit by product; in FY2025 gross profit of $2,740.2 million was less than the $2,784.6 million spent on research, sales and administration.
Sources and detail on the Datadog page5 · The one thing to watch
Datadog's largest customer reduced usage in Q3 2026, and on Nov 4, 2026 the company guided Q4 FY2026 revenue to $1,190–1,200 million, against $1,197.1 million in Q3 FY2026.
Sources and detail on the Datadog page
Where each $100 went
Each company's own receipt for its latest full fiscal year, with matching lines in the same order where both have them.
Cloudflare
Where $100 went · FY2025
| Sales and marketing | $40.1 |
|---|---|
| Research and development | $22.3 |
| General and administrative | $16.9 |
| Running the network | $24.0 |
| Interest and other expense | $0.7 |
| Income tax | $0.4 |
| Net loss (costs above money in) | −$4.4 |
| Total | $100 |
Cityfort calculation from the FY2025 10-K. Of every $100 that came in during FY2025 (revenue $2,167.9 million + interest income $131.2 million = $2,299.1 million). The lines are rounded; costs add up to $104.4, so the last line is a net loss of $4.4. Measured on revenue alone, the operating loss was $9.6 per $100. Stock-based pay ($451.5 million) sits inside the cost lines.
Datadog
Where $100 went · FY2025
| Sales and marketing | $26.5 |
|---|---|
| Research and development | $42.9 |
| General and administrative | $7.7 |
| Running the service | $19.0 |
| Interest expense | $0.3 |
| Income tax | $0.5 |
| Kept as net income | $3.0 |
| Total | $100 |
Cityfort calculation from the FY2025 10-K. Of every $100 that came in during FY2025 (revenue $3,427.2 million + interest and other income $182.5 million = $3,609.7 million). The lines are rounded, so they add to $99.9. Measured on revenue alone, operations lost $1.3 per $100. Stock-based pay ($750.7 million) sits inside the cost lines.
Line items differ because each company groups its costs its own way in its filings. Only on Cloudflare's receipt: Running the network; Interest and other expense; Net loss (costs above money in). Only on Datadog's receipt: Running the service; Interest expense; Kept as net income.
Revenue, net income and free cash flow
Up to five fiscal years for each company, drawn on one shared scale per measure. Amounts in US$ as reported (GAAP).
Revenue
Cloudflare
Datadog
See the numbers
Net income
Cloudflare
Datadog
See the numbers
Free cash flow
Cloudflare
Datadog
See the numbers
Who pays each company
Cloudflare
- Large customersPaying customers with more than $100,000 of annualized revenue (a quarter's revenue times four, usage included): 5,006 at Sep 30, 2026, up from 4,009 a year earlier. The share of revenue they pay is not disclosed.
- Other businesses, developers and individuals on paid plansCloudflare counted 332,466 paying customers in all at Dec 31, 2025, its last reported total. From 2026 it stopped reporting that number as a key metric.
Datadog
- Larger customers4,860 customers with $100,000 or more of annual recurring revenue (ARR, the company's measure) at Sep 30, 2026, up from 4,060 a year earlier. They made up about 91% of ARR; their share of GAAP revenue is not disclosed.
- All other paying customersDatadog had about 33,500 customers in all at Sep 30, 2026, up from 32,000 a year earlier. They range from small businesses to large enterprises.
Revenue by segment
Cloudflare
Not on the Cloudflare page.
Datadog
Not on the Datadog page.
Debt and cash
Cloudflare
- Debt
- $4.4B
- Cash and investments
- $5.1B
On Sep 30, 2026.
At Sep 30, 2026 Cloudflare held $5,128.7 million of cash and investments against convertible notes carried at $4,441.9 million, so cash exceeded debt by $686.8 million.
Datadog
- Debt
- $987M
- Cash and investments
- $5.2B
On Sep 30, 2026.
At Sep 30, 2026 Datadog held $5,233.6 million of cash and marketable securities against convertible notes carried at $986.6 million, so cash exceeded debt by $4,247.0 million.
Who owns each company
Cloudflare
- 2 classes of shares (votes per share: Class A common stock 1, Class B common stock 10).
- Matthew Prince (co-founder and CEO): 75.7% of its class, 39.0% of votes (as of Apr 30, 2026).
- Michelle Zatlyn (co-founder and President): 25.5% of its class, 13.4% of votes (as of Apr 30, 2026).
- Capital World Investors: 7.3% (as of Mar 31, 2026).
- 5 more holders on the Cloudflare page.
Datadog
- 2 classes of shares (votes per share: Class A common stock 1, Class B common stock 10).
- Officers and directors as a group: 6.5% of shares, 35.5% of votes (as of Mar 31, 2026).
- Olivier Pomel (co-founder and CEO): 38.7% of its class, 17.3% of votes (as of Mar 31, 2026).
- Alexis Lê-Quôc (co-founder, President and CTO): 35.5% of its class, 15.5% of votes (as of Mar 31, 2026).
- Vanguard Capital Management: 7.5% (as of Mar 31, 2026).
- 2 more holders on the Datadog page.
Sources: Cloudflare S16, S5, S17, S23, S24 · Datadog S15, S4, S19, S20, S21
Risks only one page tracks
Risks whose type the other company's page does not list. Both pages track risks of these types: governance, technology, debt, competition. Every risk is on each company's page.
Cloudflare
- Court fight over the share-class changes (legal cases)A Delaware court preliminarily blocked the Class C and preferred-stock changes on Oct 16, 2026. As of Nov 5, 2026, eight stockholder complaints had been filed: seven were consolidated into one action alleging breach of fiduciary duty, and the eighth alleges that a two-thirds vote was required. The company and its board say the claims are without merit.
- Losses and stock-based pay (other)Cloudflare had a GAAP net loss every year from FY2021 to FY2025. Stock-based pay was $451.5 million in FY2025, 20.8% of revenue, and weighted shares rose from 312.3 million in FY2021 to 348.4 million in FY2025.
- Gross margin has fallen (execution)GAAP gross margin fell from 77.3% in FY2024 to 74.5% in FY2025 and 71.2% in Q3 FY2026 (Cityfort calculation from the FY2025 10-K and Q3 FY2026 earnings release).
- Job cuts and sales leadership change (execution)A May 2026 plan cut about 20% of the workforce, with $161.7 million of charges in the first nine months of FY2026. The President of Revenue retires at the end of 2026.
Datadog
- Largest customer reduced its usage (customer or supplier concentration)Datadog's Q3 FY2026 10-Q says usage from its largest customer fell in the quarter, "which may cause a deceleration in revenue growth". The customer and its share of revenue are not disclosed. On Nov 4, 2026 Datadog guided Q4 FY2026 revenue to $1,190–1,200 million, against Q3's $1,197.1 million.
- Profit depends on interest income (other)Datadog had an operating loss of $44.4 million in FY2025; net income of $107.7 million came from $182.5 million of interest and other income on its cash and securities. The 10-K says changes in interest rates may affect that interest income.
- Stock-based pay and share count (other)Stock-based pay was $750.7 million in FY2025, 21.9% of revenue, and higher than net income in every year from FY2021 to FY2025. Diluted weighted shares rose from 309.0 million in FY2021 to 363.5 million in FY2025.
Sources: Cloudflare S5, S1, S3, S8, S18, S22 · Datadog S4, S5, S7, S1, S2
Key facts
- How does Cloudflare make money compared with Datadog?
- Businesses pay Cloudflare to protect and speed up their websites, apps and networks; most of the money goes on sales, engineers and running the network, and in FY2025 costs were higher than revenue, so it reported an operating loss. Companies pay Datadog subscription and usage fees to monitor and secure their software; most of the money goes on engineers and sales, so in FY2025 operations lost money and interest income produced the profit.
- Which is bigger by revenue, Cloudflare or Datadog?
- Cloudflare reported $2.2B of revenue in FY2025, and Datadog reported $3.4B in FY2025.
- How much net income did Cloudflare and Datadog report?
- Cloudflare reported net income of −$102M in FY2025, and Datadog reported $108M in FY2025.
- How much of every $100 did Cloudflare and Datadog keep as net income?
- Cloudflare kept −$4.4 of every $100 that came in during FY2025, and Datadog kept $3.0 in FY2025 (Cityfort calculation from each company's annual report).
- How much debt and cash do Cloudflare and Datadog have?
- Cloudflare had $4.4B of debt and $5.1B of cash and investments on Sep 30, 2026. Datadog had $987M of debt and $5.2B of cash and investments on Sep 30, 2026.
- When do Cloudflare's and Datadog's fiscal years end?
- Cloudflare: December 31 (FY2025 = year ended Dec 31, 2025). Datadog: December 31 (FY2025 = year ended Dec 31, 2025).
Sources: Cloudflare S3, S1, S5, S8 · Datadog S2, S1, S4, S7, S11, S18
Built from each company's page. Cloudflare updated Nov 6, 2026; Datadog updated Nov 6, 2026.
Sources
Cloudflare
- S1Form 10-K, fiscal year 2025 (ended December 31, 2025), Cloudflare, Inc. (SEC EDGAR), Feb 26, 2026
- S3Form 10-K, fiscal year 2023 (ended December 31, 2023), Cloudflare, Inc. (SEC EDGAR), Feb 21, 2024
- S5Form 10-Q, third quarter 2026 (quarter ended September 30, 2026), Cloudflare, Inc. (SEC EDGAR), Nov 5, 2026
- S8Cloudflare Announces Third Quarter 2026 Financial Results (8-K Exhibit 99.1), Cloudflare, Inc. (SEC EDGAR), Nov 5, 2026
- S16Definitive proxy statement (DEF 14A), 2026 annual meeting, Cloudflare, Inc. (SEC EDGAR), Jun 9, 2026
- S17Form 8-K/A, Items 5.02 and 5.07: 2026 annual meeting results (filed Jul 1, 2026), Cloudflare, Inc. (SEC EDGAR), Jul 1, 2026
- S18Form 8-K/A, Items 2.02 and 2.05: restructuring plan (filed May 7, 2026), Cloudflare, Inc. (SEC EDGAR), May 7, 2026
- S22Form 8-K Exhibit 99.2: Cloudflare Appoints Christian Smith as President of Revenue, Cloudflare, Inc. (SEC EDGAR), Nov 5, 2026
- S23Schedule 13G/A, Capital World Investors, Class A common stock (event date Mar 31, 2026), Capital World Investors (SEC EDGAR), May 14, 2026
- S24Schedule 13G/A, Baillie Gifford & Co, Class A common stock (event date Jun 30, 2026), Baillie Gifford & Co (SEC EDGAR), Jul 24, 2026
Datadog
- S1Form 10-K, fiscal year 2025 (year ended December 31, 2025), Datadog, Inc. (SEC EDGAR), Feb 18, 2026
- S2Form 10-K, fiscal year 2023 (year ended December 31, 2023), Datadog, Inc. (SEC EDGAR), Feb 23, 2024
- S4Form 10-Q, Q3 fiscal 2026 (quarter ended September 30, 2026), Datadog, Inc. (SEC EDGAR), Nov 4, 2026
- S5Form 10-Q, Q2 fiscal 2026 (quarter ended June 30, 2026), Datadog, Inc. (SEC EDGAR), Aug 6, 2026
- S7Third quarter 2026 earnings release (Form 8-K, Exhibit 99.1), Datadog, Inc. (SEC EDGAR), Nov 4, 2026
- S11Third quarter 2025 earnings release (Form 8-K, Exhibit 99.1), Datadog, Inc. (SEC EDGAR), Nov 6, 2025
- S15Definitive proxy statement for the 2026 annual meeting (DEF 14A), Datadog, Inc. (SEC EDGAR), Apr 29, 2026
- S18Form 8-K filed Dec 12, 2024: $1.0 billion 0.00% convertible senior notes due 2029 (Items 1.01, 2.03), Datadog, Inc. (SEC EDGAR), Dec 12, 2024
- S19Schedule 13G filed by Vanguard Capital Management on Datadog Class A common stock (event date Mar 31, 2026), Vanguard Capital Management (SEC EDGAR), Apr 29, 2026
- S20Schedule 13G filed by Vanguard Portfolio Management on Datadog Class A common stock (event date Mar 31, 2026), Vanguard Portfolio Management (SEC EDGAR), Apr 29, 2026
- S21Schedule 13G/A filed by The Vanguard Group on Datadog Class A common stock (event date Mar 13, 2026; 0%), The Vanguard Group (SEC EDGAR), Mar 26, 2026
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