Datadog
Large (~6,000)
OpenAI
Large (~3,500)
Best For
Datadog
Best for: Engineers who want strong comp and interesting scale challenges in cloud observability
OpenAI
Best for: Engineers who want to build frontier AI models at the company defining the industry, with elite compensation
Ratings
DatadogOpenAI
4.2
4.5
Overall
3.8
3.6
Work-Life Balance
4.3
4.6
Culture & Values
4.4
4.5
Comp & Benefits
3.8
4.3
Senior Mgmt
4.0
4.3
Career Opps
👍 80% Recommend
👤 87% CEO Approval (Olivier Pomel)
👍 90% Recommend
👤 95% CEO Approval (Sam Altman)
Culture Values
Datadog only
No unique values
OpenAI only
No unique values
Shared
⚙️ Engineering-Driven🚀 Ship Fast & Iterate🌱 Learning & Growth🎯 Direct Product Impact💎 Strong Comp & Equity
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
OpenAI
- Cutting-edge frontier AI research with world-class colleagues
- Elite compensation — top-tier TC and equity packages
- High-intensity environment — long hours and intense pace are the norm
- Internal politics and rapid org changes as the company scales
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.
OpenAI
High-intensity, mission-driven culture with world-class colleagues and top-tier comp — but expect long hours, rapid org changes, and internal politics as the company scales.
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
OpenAI — 655 jobs
💻 Engineering
317
💼 Sales / GTM
57
📋 Product
30
📊 Data
28
🧠 ML / AI
28
📣 Marketing
24
⚙️ Operations
17
⚖️ Legal
13
🎨 Design
10
👤 HR / People
9
💰 Finance
7
🎧 Support
4
Summary
Datadog scores 4.2/5.0 on Glassdoor with a 3.8 work-life balance rating. OpenAI scores 4.5/5.0 overall with a 3.6 WLB. That’s a 0.3-point gap on overall satisfaction.
Both companies share these culture values: Engineering-Driven, Ship Fast & Iterate, Learning & Growth, Direct Product Impact, Strong Comp & Equity.
On the hiring front, Datadog has 422 open roles and OpenAI has 655 open roles.