Cloudflare
Large (~4,000)
Poolside
Small (~150)
Best For
Cloudflare
Best for: Engineers who want mission-driven work building critical internet infrastructure
Poolside
Best for: AI researchers who want frontier code generation work with genuine remote flexibility and Paris offsites
Ratings
CloudflarePoolside
3.9
3.8
Overall
3.7
3.5
Work-Life Balance
4.0
3.9
Culture & Values
3.8
3.8
Comp & Benefits
3.5
3.6
Senior Mgmt
3.8
3.6
Career Opps
👍 72% Recommend
👤 77% CEO Approval (Matthew Prince)
👍 76% Recommend
👤 80% CEO Approval (Jason Warner)
Culture Values
Cloudflare only
🚀 Ship Fast & Iterate🎯 Direct Product Impact🪟 Transparent
Poolside only
🌐 Remote-Friendly🤝 Flat Hierarchy🧩 Wears Many Hats
Shared
⚙️ Engineering-Driven🌱 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
Poolside
- Remote-first with monthly Paris gatherings
- Cutting-edge code generation research
- Early-stage with limited structure
- Comp may trail larger AI labs
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.
Poolside
Choose Poolside if you want cutting-edge code AI research on a remote-first flat team (ex-GitHub CTO leadership) — but expect early-stage ambiguity and comp that trails the larger AI labs.
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
Poolside — 12 jobs
💻 Engineering
9
📊 Data
2
🧠 ML / AI
1
Summary
Cloudflare scores 3.9/5.0 on Glassdoor with a 3.7 work-life balance rating. Poolside scores 3.8/5.0 overall with a 3.5 WLB. That’s a 0.1-point gap on overall satisfaction.
Both companies share these culture values: Engineering-Driven, Learning & Growth. Cloudflare also emphasizes Ship Fast & Iterate, Direct Product Impact, Transparent. Poolside also emphasizes Remote-Friendly, Flat Hierarchy, Wears Many Hats.
On the hiring front, Cloudflare has 469 open roles and Poolside has 12 open roles.