Datadog
Large (~6,000)
Stripe
Large (~8,000)
Best For
Datadog
Best for: Engineers who want strong comp and interesting scale challenges in cloud observability
Stripe
Best for: Engineers who value code quality, writing culture, and fintech at the highest level
Ratings
DatadogStripe
4.2
4.0
Overall
3.8
3.6
Work-Life Balance
4.3
4.1
Culture & Values
4.4
4.5
Comp & Benefits
3.8
3.7
Senior Mgmt
4.0
3.8
Career Opps
👍 80% Recommend
👤 87% CEO Approval (Olivier Pomel)
👍 80% Recommend
👤 82% CEO Approval (Patrick Collison)
Culture Values
Datadog only
🚀 Ship Fast & Iterate
Stripe only
🪟 Transparent
Shared
⚙️ Engineering-Driven🌱 Learning & Growth🎯 Direct Product Impact💎 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
Stripe
- Engineering culture is elite — code quality and writing culture are best-in-class
- Top compensation in fintech — competitive base, equity, and benefits
- Perfectionism can slow shipping — high bar sometimes means slower velocity
- The 2022-23 layoffs affected morale — company has been rebuilding confidence
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.
Stripe
Choose Stripe if you want elite engineering culture with top comp — but perfectionism can slow shipping velocity.
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
Stripe — 510 jobs
💻 Engineering
111
💼 Sales / GTM
98
📋 Product
51
⚙️ Operations
43
📣 Marketing
34
💰 Finance
21
📊 Data
20
👤 HR / People
15
🎨 Design
12
⚖️ Legal
12
🧠 ML / AI
9
🎧 Support
3
Summary
Datadog scores 4.2/5.0 on Glassdoor with a 3.8 work-life balance rating. Stripe scores 4.0/5.0 overall with a 3.6 WLB. That’s a 0.2-point gap on overall satisfaction.
Both companies share these culture values: Engineering-Driven, Learning & Growth, Direct Product Impact, Strong Comp & Equity. Datadog also emphasizes Ship Fast & Iterate. Stripe also emphasizes Transparent.
On the hiring front, Datadog has 451 open roles and Stripe has 510 open roles.