Brex
Large (~1,600)
Datadog
Large (~6,000)
Best For
Brex
Best for: Engineers who want to build AI-powered fintech at massive scale with smart colleagues
Datadog
Best for: Engineers who want strong comp and interesting scale challenges in cloud observability
Ratings
BrexDatadog
4.0
4.2
Overall
3.9
3.8
Work-Life Balance
3.8
4.3
Culture & Values
4.0
4.4
Comp & Benefits
3.5
3.8
Senior Mgmt
3.6
4.0
Career Opps
👍 77% Recommend
👤 71% CEO Approval (Pedro Franceschi)
👍 80% Recommend
👤 87% CEO Approval (Olivier Pomel)
Culture Values
Brex only
🪟 Transparent🌐 Remote-Friendly
Datadog only
💎 Strong Comp & Equity
Shared
🚀 Ship Fast & Iterate⚙️ Engineering-Driven🎯 Direct Product Impact🌱 Learning & Growth
Pros & Cons
Brex
- Innovation-driven culture with incredibly smart, passionate, and supportive colleagues
- Remote-first with strong benefits — time off actively encouraged with flexible scheduling
- Culture of overworking — many departments understaffed relative to workload expectations
- Multiple rounds of layoffs in recent years have created uncertainty and morale challenges
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
Brex
Choose Brex if you want to build AI-powered fintech at massive scale with smart colleagues — but expect intense workloads and some organizational instability from recent layoffs.
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
Brex — 247 jobs
💼 Sales / GTM
77
💻 Engineering
54
📋 Product
20
👤 HR / People
16
🎨 Design
15
📣 Marketing
11
📊 Data
10
⚙️ Operations
7
⚖️ Legal
6
💰 Finance
5
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
Brex scores 4.0/5.0 on Glassdoor with a 3.9 work-life balance rating. Datadog scores 4.2/5.0 overall with a 3.8 WLB. That’s a 0.2-point gap on overall satisfaction.
Both companies share these culture values: Ship Fast & Iterate, Engineering-Driven, Direct Product Impact, Learning & Growth. Brex also emphasizes Transparent, Remote-Friendly. Datadog also emphasizes Strong Comp & Equity.
On the hiring front, Brex has 247 open roles and Datadog has 451 open roles.