Datadog
Large (~6,000)
Poolside
Small (~150)
Best For
Datadog
Best for: Engineers who want strong comp and interesting scale challenges in cloud observability
Poolside
Best for: AI researchers who want frontier code generation work with genuine remote flexibility and Paris offsites
Ratings
DatadogPoolside
4.2
3.8
Overall
3.8
3.5
Work-Life Balance
4.3
3.9
Culture & Values
4.4
3.8
Comp & Benefits
3.8
3.6
Senior Mgmt
4.0
3.6
Career Opps
👍 80% Recommend
👤 87% CEO Approval (Olivier Pomel)
👍 76% Recommend
👤 80% CEO Approval (Jason Warner)
Culture Values
Datadog only
🚀 Ship Fast & Iterate🎯 Direct Product Impact💎 Strong Comp & Equity
Poolside only
🌐 Remote-Friendly🤝 Flat Hierarchy🧩 Wears Many Hats
Shared
⚙️ Engineering-Driven🌱 Learning & Growth
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
Poolside
- Remote-first with monthly Paris gatherings
- Cutting-edge code generation research
- Early-stage with limited structure
- Comp may trail larger AI labs
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.
Poolside
Choose Poolside if you want cutting-edge code AI research on a remote-first flat team (ex-GitHub CTO leadership) — but expect early-stage ambiguity and comp that trails the larger AI labs.
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
Poolside — 12 jobs
💻 Engineering
9
📊 Data
2
🧠 ML / AI
1
Summary
Datadog scores 4.2/5.0 on Glassdoor with a 3.8 work-life balance rating. Poolside scores 3.8/5.0 overall with a 3.5 WLB. That’s a 0.4-point gap on overall satisfaction.
Both companies share these culture values: Engineering-Driven, Learning & Growth. Datadog also emphasizes Ship Fast & Iterate, Direct Product Impact, Strong Comp & Equity. Poolside also emphasizes Remote-Friendly, Flat Hierarchy, Wears Many Hats.
On the hiring front, Datadog has 422 open roles and Poolside has 12 open roles.