Datadog
Large (~6,000)
Plaid
Mid (~800)
Best For
Datadog
Best for: Engineers who want strong comp and interesting scale challenges in cloud observability
Plaid
Best for: Engineers who want transparent leadership and real fintech impact at a top-rated company
Ratings
DatadogPlaid
4.2
4.6
Overall
3.8
4.2
Work-Life Balance
4.3
4.2
Culture & Values
4.4
4.1
Comp & Benefits
3.8
4.0
Senior Mgmt
4.0
3.9
Career Opps
👍 80% Recommend
👤 87% CEO Approval (Olivier Pomel)
👍 91% Recommend
👤 83% CEO Approval (Zach Perret)
Culture Values
Datadog only
🚀 Ship Fast & Iterate💎 Strong Comp & Equity
Plaid only
🪟 Transparent🛡️ Safe to Fail🌈 Diverse & Inclusive
Shared
⚙️ Engineering-Driven🌱 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
Plaid
- 91% of employees recommend — highly accessible and transparent senior leadership
- Strong engineering culture with competitive compensation (4.1/5 comp rating) and real product impact
- Organizational changes can create uncertainty as the company scales
- Career opportunities rated 3.9/5 — growth paths may vary by department
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.
Plaid
Choose Plaid if you want top-tier engineering culture, transparent leadership, and real fintech impact — but expect some growing pains as the company navigates organizational change.
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
Plaid — 94 jobs
💻 Engineering
25
💼 Sales / GTM
23
📣 Marketing
8
📋 Product
8
📊 Data
7
🧠 ML / AI
4
⚙️ Operations
3
🎨 Design
2
👤 HR / People
2
⚖️ Legal
2
💰 Finance
1
Summary
Datadog scores 4.2/5.0 on Glassdoor with a 3.8 work-life balance rating. Plaid scores 4.6/5.0 overall with a 4.2 WLB. That’s a 0.4-point gap on overall satisfaction.
Both companies share these culture values: Engineering-Driven, Learning & Growth, Direct Product Impact. Datadog also emphasizes Ship Fast & Iterate, Strong Comp & Equity. Plaid also emphasizes Transparent, Safe to Fail, Diverse & Inclusive.
On the hiring front, Datadog has 451 open roles and Plaid has 94 open roles.