Cursor (Anysphere)
Small (~50)
Datadog
Large (~6,000)
Best For
Cursor (Anysphere)
Best for: Generalist engineers who want extreme ownership at the most-loved AI code editor
Datadog
Best for: Engineers who want strong comp and interesting scale challenges in cloud observability
Ratings
Cursor (Anysphere)Datadog
4.0
4.2
Overall
3.5
3.8
Work-Life Balance
4.0
4.3
Culture & Values
4.2
4.4
Comp & Benefits
3.8
3.8
Senior Mgmt
3.5
4.0
Career Opps
👍 85% Recommend
👤 90% CEO Approval (Michael Truell)
👍 80% Recommend
👤 87% CEO Approval (Olivier Pomel)
Culture Values
Cursor (Anysphere) only
🤝 Flat Hierarchy🧩 Wears Many Hats
Datadog only
🌱 Learning & Growth💎 Strong Comp & Equity
Shared
🚀 Ship Fast & Iterate⚙️ Engineering-Driven🎯 Direct Product Impact
Pros & Cons
Cursor (Anysphere)
- Building the most-loved AI code editor — massive developer love and daily impact
- Tiny team, extreme ownership — every person shapes the product directly
- Extremely small team = no specialists; everyone does everything
- Intense pace — the speed of shipping can be relentless
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
Cursor (Anysphere)
Choose Cursor if you want to shape the future of AI-assisted coding on a tiny team — but the pace is relentless.
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
Cursor (Anysphere) — 63 jobs
💼 Sales / GTM
22
💻 Engineering
19
📊 Data
4
🎨 Design
3
🧠 ML / AI
3
⚖️ Legal
2
👤 HR / People
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
Cursor (Anysphere) scores 4.0/5.0 on Glassdoor with a 3.5 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. Cursor (Anysphere) also emphasizes Flat Hierarchy, Wears Many Hats. Datadog also emphasizes Learning & Growth, Strong Comp & Equity.
On the hiring front, Cursor (Anysphere) has 63 open roles and Datadog has 451 open roles.