Cloudflare
Large (~4,000)
Datadog
Large (~6,000)
Best For
Cloudflare
Best for: Engineers who want mission-driven work building critical internet infrastructure
Datadog
Best for: Engineers who want strong comp and interesting scale challenges in cloud observability
Ratings
CloudflareDatadog
3.9
4.2
Overall
3.7
3.8
Work-Life Balance
4.0
4.3
Culture & Values
3.8
4.4
Comp & Benefits
3.5
3.8
Senior Mgmt
3.8
4.0
Career Opps
👍 72% Recommend
👤 77% CEO Approval (Matthew Prince)
👍 80% Recommend
👤 87% CEO Approval (Olivier Pomel)
Culture Values
Cloudflare only
🪟 Transparent
Datadog only
💎 Strong Comp & Equity
Shared
⚙️ Engineering-Driven🚀 Ship Fast & Iterate🎯 Direct Product Impact🌱 Learning & Growth
Pros & Cons
Cloudflare
- Mission-driven company building critical internet infrastructure — meaningful work with real impact
- Smart colleagues and a culture that values innovation, shipping quickly, and technical excellence
- Compensation can lag behind FAANG competitors, especially base salary
- Some teams experience high pressure and demanding workloads with uneven management quality
Datadog
- Excellent compensation and equity — stock has been a genuine wealth builder for early employees
- Strong engineering culture with smart coworkers and interesting technical challenges at scale
- Fast pace can lead to long hours and pressure to deliver, work-life balance varies by team
- Rapid growth has led to organizational growing pains and bureaucracy creeping in
Bottom Line
Cloudflare
Choose Cloudflare if you want mission-driven work building critical internet infrastructure with sharp engineers — but compensation lags FAANG and pressure can be high.
Datadog
Choose Datadog if you want strong comp, interesting scale challenges in observability, and a fast-paced engineering culture — but expect long hours and growing bureaucracy.
Open Roles
Cloudflare — 533 jobs
💼 Sales / GTM
250
💻 Engineering
151
📋 Product
26
📣 Marketing
13
📊 Data
12
👤 HR / People
8
⚙️ Operations
5
⚖️ Legal
4
🧠 ML / AI
4
🎨 Design
2
💰 Finance
2
Datadog — 451 jobs
💼 Sales / GTM
217
💻 Engineering
118
📋 Product
28
📣 Marketing
15
👤 HR / People
8
🧠 ML / AI
8
🎨 Design
7
⚙️ Operations
6
⚖️ Legal
3
📊 Data
1
💰 Finance
1
Summary
Cloudflare scores 3.9/5.0 on Glassdoor with a 3.7 work-life balance rating. Datadog scores 4.2/5.0 overall with a 3.8 WLB. That’s a 0.3-point gap on overall satisfaction.
Both companies share these culture values: Engineering-Driven, Ship Fast & Iterate, Direct Product Impact, Learning & Growth. Cloudflare also emphasizes Transparent. Datadog also emphasizes Strong Comp & Equity.
On the hiring front, Cloudflare has 533 open roles and Datadog has 451 open roles.