Datadog
Large (~6,000)
Sierra
Large (~500)
Best For
Datadog
Best for: Engineers who want strong comp and interesting scale challenges in cloud observability
Sierra
Best for: Builders who want to work with proven Salesforce and Google leadership on enterprise AI agents
Ratings
DatadogSierra
4.2
4.0
Overall
3.8
3.5
Work-Life Balance
4.3
4.1
Culture & Values
4.4
4.0
Comp & Benefits
3.8
3.8
Senior Mgmt
4.0
3.8
Career Opps
👍 80% Recommend
👤 87% CEO Approval (Olivier Pomel)
👍 80% Recommend
👤 84% CEO Approval (Bret Taylor)
Culture Values
Datadog only
🎯 Direct Product Impact
Sierra only
No unique values
Shared
⚙️ Engineering-Driven🚀 Ship Fast & Iterate🌱 Learning & Growth💎 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
Sierra
- Elite founders with proven track records
- Strong equity at $10B valuation
- In-person-first culture
- Competitive intensity may not suit everyone
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.
Sierra
Choose Sierra if you want elite founders (Bret Taylor, Clay Bavor) and strong equity at a $10B enterprise AI company — but it's in-person-first and the competitive intensity won't suit everyone.
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
Sierra — 134 jobs
💻 Engineering
42
💼 Sales / GTM
27
📋 Product
15
👤 HR / People
7
🎨 Design
5
⚖️ Legal
5
📣 Marketing
5
⚙️ Operations
5
📊 Data
2
💰 Finance
1
Summary
Datadog scores 4.2/5.0 on Glassdoor with a 3.8 work-life balance rating. Sierra scores 4.0/5.0 overall with a 3.5 WLB. That’s a 0.2-point gap on overall satisfaction.
Both companies share these culture values: Engineering-Driven, Ship Fast & Iterate, Learning & Growth, Strong Comp & Equity. Datadog also emphasizes Direct Product Impact.
On the hiring front, Datadog has 422 open roles and Sierra has 134 open roles.