Airbnb
Large (~7,300)
Datadog
Large (~6,000)
Best For
Airbnb
Best for: Engineers who want Live Anywhere flexibility with strong comp and no pay cuts
Datadog
Best for: Engineers who want strong comp and interesting scale challenges in cloud observability
Ratings
AirbnbDatadog
4.1
4.2
Overall
4.0
3.8
Work-Life Balance
4.2
4.3
Culture & Values
4.2
4.4
Comp & Benefits
3.5
3.8
Senior Mgmt
3.5
4.0
Career Opps
👍 80% Recommend
👤 87% CEO Approval (Brian Chesky)
👍 80% Recommend
👤 87% CEO Approval (Olivier Pomel)
Culture Values
Airbnb only
🌐 Remote-Friendly⚖️ Work-Life Balance🌈 Diverse & Inclusive🔓 Open Source
Datadog only
⚙️ Engineering-Driven🚀 Ship Fast & Iterate🌱 Learning & Growth🎯 Direct Product Impact
Shared
💎 Strong Comp & Equity
Pros & Cons
Airbnb
- Live and Work Anywhere policy — genuine remote flexibility with no pay cuts
- Strong compensation and benefits with quarterly travel credits and educational stipends
- Limited career growth — senior roles often filled externally, promotions are slow
- Post-IPO cultural shift — increasing bureaucracy and internal politics at mid-to-senior levels
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
Bottom Line
Airbnb
Choose Airbnb if you want genuine remote flexibility and travel perks — but promotions are slow and bureaucracy is growing.
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.
Open Roles
Airbnb — 251 jobs
💻 Engineering
71
🎧 Support
19
📊 Data
18
⚙️ Operations
13
📋 Product
13
🧠 ML / AI
11
💼 Sales / GTM
10
📣 Marketing
8
⚖️ Legal
4
💰 Finance
2
👤 HR / People
2
🎨 Design
1
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
Summary
Airbnb scores 4.1/5.0 on Glassdoor with a 4.0 work-life balance rating. Datadog scores 4.2/5.0 overall with a 3.8 WLB. That’s a 0.1-point gap on overall satisfaction.
Both companies share these culture values: Strong Comp & Equity. Airbnb also emphasizes Remote-Friendly, Work-Life Balance, Diverse & Inclusive, Open Source. Datadog also emphasizes Engineering-Driven, Ship Fast & Iterate, Learning & Growth, Direct Product Impact.
On the hiring front, Airbnb has 251 open roles and Datadog has 451 open roles.