Datadog
Large (~6,000)
Writer
Mid (~400)
Best For
Datadog
Best for: Engineers who want strong comp and interesting scale challenges in cloud observability
Writer
Best for: Professionals interested in Writer
Ratings
DatadogWriter
4.2
3.5
Overall
3.8
2.7
Work-Life Balance
4.3
3.6
Culture & Values
4.4
3.5
Comp & Benefits
3.8
3.3
Senior Mgmt
4.0
3.3
Career Opps
👍 80% Recommend
👤 87% CEO Approval (Olivier Pomel)
👍 70% Recommend
👤 74% CEO Approval (CEO)
Culture Values
Datadog only
🌱 Learning & Growth🎯 Direct Product Impact💎 Strong Comp & Equity
Writer only
🔓 Open Source
Shared
⚙️ Engineering-Driven🚀 Ship Fast & Iterate
Pros & Cons
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
Writer
- Real AI engineering with proprietary LLMs — not just wrapping OpenAI APIs
- Strong enterprise traction and visionary product direction
- Intense work culture with very high expectations and limited work-life balance
- Growing management layers creating organizational friction
Bottom Line
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.
Writer
Writer — check Glassdoor for detailed reviews.
Open Roles
Datadog — 422 jobs
💼 Sales / GTM
218
💻 Engineering
83
📋 Product
28
📣 Marketing
12
👤 HR / People
8
🧠 ML / AI
8
🎨 Design
6
⚖️ Legal
3
⚙️ Operations
3
📊 Data
2
💰 Finance
1
Writer — 49 jobs
💻 Engineering
16
💼 Sales / GTM
12
🎨 Design
1
⚙️ Operations
1
📋 Product
1
Summary
Datadog scores 4.2/5.0 on Glassdoor with a 3.8 work-life balance rating. Writer scores 3.5/5.0 overall with a 2.7 WLB. That’s a 0.7-point gap on overall satisfaction.
Both companies share these culture values: Engineering-Driven, Ship Fast & Iterate. Datadog also emphasizes Learning & Growth, Direct Product Impact, Strong Comp & Equity. Writer also emphasizes Open Source.
On the hiring front, Datadog has 422 open roles and Writer has 49 open roles.