Datadog
Large (~6,000)
Weaviate
Small (~110)
Best For
Datadog
Best for: Engineers who want strong comp and interesting scale challenges in cloud observability
Weaviate
Best for: Engineers who want open-source vector database work with true remote-first, async culture
Ratings
DatadogWeaviate
4.2
4.3
Overall
3.8
4.2
Work-Life Balance
4.3
4.5
Culture & Values
4.4
4.0
Comp & Benefits
3.8
4.2
Senior Mgmt
4.0
4.0
Career Opps
👍 80% Recommend
👤 87% CEO Approval (Olivier Pomel)
👍 85% Recommend
👤 90% CEO Approval (Bob van Luijt)
Culture Values
Datadog only
⚙️ Engineering-Driven🚀 Ship Fast & Iterate🌱 Learning & Growth🎯 Direct Product Impact💎 Strong Comp & Equity
Weaviate only
🌐 Remote-Friendly📡 Async-First🤝 Flat Hierarchy🔓 Open Source⚖️ Work-Life Balance🌈 Diverse & Inclusive🛡️ Safe to Fail
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
Weaviate
- Excellent remote-first culture — async workflows, timezone respect, and high autonomy
- Flat, ego-free culture — your voice is heard from day 1 regardless of title
- Time zone challenges inherent to a fully distributed global team
- Startup growing pains — processes still being established, things evolve quickly
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.
Weaviate
Choose Weaviate if you want excellent remote culture with flat hierarchy and open-source mission — but expect startup growing pains.
Open Roles
Datadog — 451 jobs
💼 Sales / GTM
217
💻 Engineering
118
📋 Product
28
📣 Marketing
15
👤 HR / People
8
🧠 ML / AI
8
🎨 Design
7
⚙️ Operations
6
⚖️ Legal
3
📊 Data
1
💰 Finance
1
Weaviate — 3 jobs
💼 Sales / GTM
2
💻 Engineering
1
Summary
Datadog scores 4.2/5.0 on Glassdoor with a 3.8 work-life balance rating. Weaviate scores 4.3/5.0 overall with a 4.2 WLB. That’s a 0.1-point gap on overall satisfaction.
On the hiring front, Datadog has 451 open roles and Weaviate has 3 open roles.