Datadog
Large (~6,000)
Labelbox
Medium (~350)
Best For
Datadog
Best for: Engineers who want strong comp and interesting scale challenges in cloud observability
Labelbox
Best for: ML infrastructure engineers building data labeling and training platforms for frontier AI labs and enterprises
Ratings
DatadogLabelbox
4.2
3.8
Overall
3.8
3.6
Work-Life Balance
4.3
3.8
Culture & Values
4.4
3.6
Comp & Benefits
3.8
3.5
Senior Mgmt
4.0
3.6
Career Opps
👍 80% Recommend
👤 87% CEO Approval (Olivier Pomel)
👍 72% Recommend
👤 78% CEO Approval (Manu Sharma)
Culture Values
Datadog only
🌱 Learning & Growth🎯 Direct Product Impact
Labelbox only
🌈 Diverse & Inclusive
Shared
⚙️ Engineering-Driven🚀 Ship Fast & Iterate💎 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
Labelbox
- Competitive compensation and equity
- Working with top AI labs as customers
- Rapid growth creates organizational churn
- Some teams move faster than others
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.
Labelbox
Choose Labelbox if you want to work on the data side of AI — labeling, evaluation, and training infrastructure used by frontier AI teams — with moderate SF-based intensity.
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
Labelbox — 9 jobs
💻 Engineering
3
🧠 ML / AI
3
📊 Data
1
Summary
Datadog scores 4.2/5.0 on Glassdoor with a 3.8 work-life balance rating. Labelbox scores 3.8/5.0 overall with a 3.6 WLB. That’s a 0.4-point gap on overall satisfaction.
Both companies share these culture values: Engineering-Driven, Ship Fast & Iterate, Strong Comp & Equity. Datadog also emphasizes Learning & Growth, Direct Product Impact. Labelbox also emphasizes Diverse & Inclusive.
On the hiring front, Datadog has 422 open roles and Labelbox has 9 open roles.