Contentful
Large (~1,000)
Hebbia
Small (~140)
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
Hebbia
Best for: Engineers who want a famously kind, high-EQ team building cutting-edge AI for finance and legal professionals
Ratings
ContentfulHebbia
3.4
4.4
Overall
3.8
3.2
Work-Life Balance
3.5
4.5
Culture & Values
3.4
4.4
Comp & Benefits
3.2
4.2
Senior Mgmt
3.2
4.2
Career Opps
👍 68% Recommend
👤 71% CEO Approval (Jaspar Carmichael-Jack)
👍 88% Recommend
👤 92% CEO Approval (George Sivulka)
Culture Values
Contentful only
🌐 Remote-Friendly
Hebbia only
🚀 Ship Fast & Iterate🧩 Wears Many Hats
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
Hebbia
- Incredible culture and smart, kind team
- Cutting-edge AI work in finance
- Very long hours expected
- Fully in-office, no flexibility
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.
Hebbia
Choose Hebbia if you want one of the most collegial cultures in AI (4.4 Glassdoor, 88% recommend) and direct impact in fintech — but expect very long hours and fully in-office, no remote flexibility.
Open Roles
Contentful — 111 jobs
💻 Engineering
56
📋 Product
17
💼 Sales / GTM
15
📊 Data
6
📣 Marketing
2
🧠 ML / AI
2
🎨 Design
1
⚖️ Legal
1
🎧 Support
1
Hebbia — 32 jobs
💼 Sales / GTM
10
💻 Engineering
8
📊 Data
2
🎨 Design
2
💰 Finance
1
👤 HR / People
1
🧠 ML / AI
1
Summary
Contentful scores 3.4/5.0 on Glassdoor with a 3.8 work-life balance rating. Hebbia scores 4.4/5.0 overall with a 3.2 WLB. That’s a 1.0-point gap on overall satisfaction.
Both companies share these culture values: Engineering-Driven, Learning & Growth, Direct Product Impact. Contentful also emphasizes Remote-Friendly. Hebbia also emphasizes Ship Fast & Iterate, Wears Many Hats.
On the hiring front, Contentful has 111 open roles and Hebbia has 32 open roles.