Datadog
Large (~6,000)
Hebbia
Small (~140)
Best For
Datadog
Best for: Engineers who want strong comp and interesting scale challenges in cloud observability
Hebbia
Best for: Engineers who want a famously kind, high-EQ team building cutting-edge AI for finance and legal professionals
Ratings
DatadogHebbia
4.2
4.4
Overall
3.8
3.2
Work-Life Balance
4.3
4.5
Culture & Values
4.4
4.4
Comp & Benefits
3.8
4.2
Senior Mgmt
4.0
4.2
Career Opps
👍 80% Recommend
👤 87% CEO Approval (Olivier Pomel)
👍 88% Recommend
👤 92% CEO Approval (George Sivulka)
Culture Values
Datadog only
💎 Strong Comp & Equity
Hebbia only
🧩 Wears Many Hats
Shared
⚙️ Engineering-Driven🚀 Ship Fast & Iterate🌱 Learning & Growth🎯 Direct Product Impact
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
Hebbia
- Incredible culture and smart, kind team
- Cutting-edge AI work in finance
- Very long hours expected
- Fully in-office, no flexibility
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.
Hebbia
Choose Hebbia if you want one of the most collegial cultures in AI (4.4 Glassdoor, 88% recommend) and direct impact in fintech — but expect very long hours and fully in-office, no remote flexibility.
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
Hebbia — 32 jobs
💼 Sales / GTM
10
💻 Engineering
8
📊 Data
2
🎨 Design
2
💰 Finance
1
👤 HR / People
1
🧠 ML / AI
1
Summary
Datadog scores 4.2/5.0 on Glassdoor with a 3.8 work-life balance rating. Hebbia scores 4.4/5.0 overall with a 3.2 WLB. That’s a 0.2-point gap on overall satisfaction.
Both companies share these culture values: Engineering-Driven, Ship Fast & Iterate, Learning & Growth, Direct Product Impact. Datadog also emphasizes Strong Comp & Equity. Hebbia also emphasizes Wears Many Hats.
On the hiring front, Datadog has 422 open roles and Hebbia has 32 open roles.