Cloudflare
Large (~4,000)
Hebbia
Small (~140)
Best For
Cloudflare
Best for: Engineers who want mission-driven work building critical internet infrastructure
Hebbia
Best for: Engineers who want a famously kind, high-EQ team building cutting-edge AI for finance and legal professionals
Ratings
CloudflareHebbia
3.9
4.4
Overall
3.7
3.2
Work-Life Balance
4.0
4.5
Culture & Values
3.8
4.4
Comp & Benefits
3.5
4.2
Senior Mgmt
3.8
4.2
Career Opps
👍 72% Recommend
👤 77% CEO Approval (Matthew Prince)
👍 88% Recommend
👤 92% CEO Approval (George Sivulka)
Culture Values
Cloudflare only
🪟 Transparent
Hebbia only
🧩 Wears Many Hats
Shared
⚙️ Engineering-Driven🚀 Ship Fast & Iterate🎯 Direct Product Impact🌱 Learning & Growth
Pros & Cons
Cloudflare
- Mission-driven company building critical internet infrastructure — meaningful work with real impact
- Smart colleagues and a culture that values innovation, shipping quickly, and technical excellence
- Compensation can lag behind FAANG competitors, especially base salary
- Some teams experience high pressure and demanding workloads with uneven management quality
Hebbia
- Incredible culture and smart, kind team
- Cutting-edge AI work in finance
- Very long hours expected
- Fully in-office, no flexibility
Bottom Line
Cloudflare
Choose Cloudflare if you want mission-driven work building critical internet infrastructure with sharp engineers — but compensation lags FAANG and pressure can be high.
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
Cloudflare — 469 jobs
💼 Sales / GTM
226
💻 Engineering
127
📋 Product
19
📣 Marketing
18
📊 Data
10
⚙️ Operations
7
👤 HR / People
6
⚖️ Legal
6
🧠 ML / AI
4
💰 Finance
1
Hebbia — 32 jobs
💼 Sales / GTM
10
💻 Engineering
8
📊 Data
2
🎨 Design
2
💰 Finance
1
👤 HR / People
1
🧠 ML / AI
1
Summary
Cloudflare scores 3.9/5.0 on Glassdoor with a 3.7 work-life balance rating. Hebbia scores 4.4/5.0 overall with a 3.2 WLB. That’s a 0.5-point gap on overall satisfaction.
Both companies share these culture values: Engineering-Driven, Ship Fast & Iterate, Direct Product Impact, Learning & Growth. Cloudflare also emphasizes Transparent. Hebbia also emphasizes Wears Many Hats.
On the hiring front, Cloudflare has 469 open roles and Hebbia has 32 open roles.