Chainguard
Mid (~350)
Datadog
Large (~6,000)
Best For
Chainguard
Best for: Security-minded engineers who want remote-first open-source work with strong comp
Datadog
Best for: Engineers who want strong comp and interesting scale challenges in cloud observability
Ratings
ChainguardDatadog
4.5
4.2
Overall
4.2
3.8
Work-Life Balance
4.3
4.3
Culture & Values
4.2
4.4
Comp & Benefits
4.1
3.8
Senior Mgmt
4.0
4.0
Career Opps
👍 88% Recommend
👤 90% CEO Approval (Dan Lorenc)
👍 80% Recommend
👤 87% CEO Approval (Olivier Pomel)
Culture Values
Chainguard only
🌐 Remote-Friendly🔓 Open Source⚖️ Work-Life Balance
Datadog only
🚀 Ship Fast & Iterate🌱 Learning & Growth🎯 Direct Product Impact
Shared
⚙️ Engineering-Driven💎 Strong Comp & Equity
Pros & Cons
Chainguard
- Fully remote with outstanding benefits — 100% employer-paid insurance for employees and families
- Founders are practitioners who understand what engineers and security teams need
- Growing so fast that some inefficiencies exist, though improving
- Fully remote means you miss in-person interactions with teammates
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
Chainguard
Choose Chainguard if you want to build supply chain security tools in a remote, open-source-first culture with strong equity — but expect a fast-moving startup pace.
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
Chainguard — 63 jobs
💼 Sales / GTM
27
💻 Engineering
24
📣 Marketing
3
📋 Product
2
🎨 Design
1
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
Summary
Chainguard scores 4.5/5.0 on Glassdoor with a 4.2 work-life balance rating. Datadog scores 4.2/5.0 overall with a 3.8 WLB. That’s a 0.3-point gap on overall satisfaction.
Both companies share these culture values: Engineering-Driven, Strong Comp & Equity. Chainguard also emphasizes Remote-Friendly, Open Source, Work-Life Balance. Datadog also emphasizes Ship Fast & Iterate, Learning & Growth, Direct Product Impact.
On the hiring front, Chainguard has 63 open roles and Datadog has 422 open roles.