Datadog
Large (~6,000)
GitLab
Large (~2,500)
Best For
Datadog
Best for: Engineers who want strong comp and interesting scale challenges in cloud observability
GitLab
Best for: Engineers who want a fully remote, async-first culture with radical transparency
Ratings
DatadogGitLab
4.2
3.9
Overall
3.8
3.9
Work-Life Balance
4.3
4.0
Culture & Values
4.4
3.8
Comp & Benefits
3.8
3.5
Senior Mgmt
4.0
3.7
Career Opps
👍 80% Recommend
👤 87% CEO Approval (Olivier Pomel)
👍 75% Recommend
👤 70% CEO Approval (Sid Sijbrandij)
Culture Values
Datadog only
⚙️ Engineering-Driven🚀 Ship Fast & Iterate🌱 Learning & Growth🎯 Direct Product Impact💎 Strong Comp & Equity
GitLab only
🌐 Remote-Friendly📡 Async-First🪟 Transparent🔓 Open Source⚖️ Work-Life Balance
Shared
None
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
GitLab
- Best-in-class all-remote culture — truly async-first with genuine flexibility
- Radically transparent company with a public handbook and open processes
- Revenue organization has seen quota chaos and low morale
- Some leadership instability at the C-suite level
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.
GitLab
Choose GitLab if you want the gold standard of all-remote work with public handbook and async processes — but expect bureaucracy at scale and comp below top-tier.
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
GitLab — 195 jobs
💻 Engineering
79
💼 Sales / GTM
67
📋 Product
10
⚖️ Legal
5
📊 Data
4
🎨 Design
4
📣 Marketing
4
👤 HR / People
2
⚙️ Operations
2
Summary
Datadog scores 4.2/5.0 on Glassdoor with a 3.8 work-life balance rating. GitLab scores 3.9/5.0 overall with a 3.9 WLB. That’s a 0.3-point gap on overall satisfaction.
On the hiring front, Datadog has 422 open roles and GitLab has 195 open roles.