Contentful
Large (~1,000)
Datadog
Large (~6,000)
Best For
Contentful
Best for: Backend and full-stack engineers who want to work on developer-facing content infrastructure with remote flexibility and an established product used by major brands
Datadog
Best for: Engineers who want strong comp and interesting scale challenges in cloud observability
Ratings
ContentfulDatadog
3.4
4.2
Overall
3.8
3.8
Work-Life Balance
3.5
4.3
Culture & Values
3.4
4.4
Comp & Benefits
3.2
3.8
Senior Mgmt
3.2
4.0
Career Opps
👍 68% Recommend
👤 71% CEO Approval (Jaspar Carmichael-Jack)
👍 80% Recommend
👤 87% CEO Approval (Olivier Pomel)
Culture Values
Contentful only
🌐 Remote-Friendly
Datadog only
🚀 Ship Fast & Iterate💎 Strong Comp & Equity
Shared
⚙️ Engineering-Driven🌱 Learning & Growth🎯 Direct Product Impact
Pros & Cons
Contentful
- Flexible remote/hybrid setup with strong distributed team culture
- Talented and humble engineering team with approachable, responsive leadership
- Stagnating product development with competition overtaking in key areas
- Internal promotions are difficult with pay disparities between long-tenured and new hires
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
Contentful
Pioneer in headless CMS with genuine remote flexibility, but Glassdoor is below average (3.4, 68% recommend) — reviews mention leadership instability and limited career progression.
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
Contentful — 114 jobs
💻 Engineering
56
📋 Product
17
💼 Sales / GTM
13
📊 Data
6
📣 Marketing
4
🧠 ML / AI
2
⚖️ Legal
1
🎧 Support
1
Datadog — 433 jobs
💼 Sales / GTM
208
💻 Engineering
112
📋 Product
26
📣 Marketing
16
👤 HR / People
8
🧠 ML / AI
8
🎨 Design
5
⚙️ Operations
5
⚖️ Legal
3
📊 Data
1
💰 Finance
1
Summary
Contentful scores 3.4/5.0 on Glassdoor with a 3.8 work-life balance rating. Datadog scores 4.2/5.0 overall with a 3.8 WLB. That’s a 0.8-point gap on overall satisfaction.
Both companies share these culture values: Engineering-Driven, Learning & Growth, Direct Product Impact. Contentful also emphasizes Remote-Friendly. Datadog also emphasizes Ship Fast & Iterate, Strong Comp & Equity.
On the hiring front, Contentful has 114 open roles and Datadog has 433 open roles.