Hebbia
Small (~140)
Poolside
Small (~150)
Best For
Hebbia
Best for: Engineers who want a famously kind, high-EQ team building cutting-edge AI for finance and legal professionals
Poolside
Best for: AI researchers who want frontier code generation work with genuine remote flexibility and Paris offsites
Ratings
HebbiaPoolside
4.4
3.8
Overall
3.2
3.5
Work-Life Balance
4.5
3.9
Culture & Values
4.4
3.8
Comp & Benefits
4.2
3.6
Senior Mgmt
4.2
3.6
Career Opps
👍 88% Recommend
👤 92% CEO Approval (George Sivulka)
👍 76% Recommend
👤 80% CEO Approval (Jason Warner)
Culture Values
Hebbia only
🚀 Ship Fast & Iterate🎯 Direct Product Impact
Poolside only
🌐 Remote-Friendly🤝 Flat Hierarchy
Shared
⚙️ Engineering-Driven🌱 Learning & Growth🧩 Wears Many Hats
Pros & Cons
Hebbia
- Incredible culture and smart, kind team
- Cutting-edge AI work in finance
- Very long hours expected
- Fully in-office, no flexibility
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
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.
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
Hebbia — 32 jobs
💼 Sales / GTM
10
💻 Engineering
8
📊 Data
2
🎨 Design
2
💰 Finance
1
👤 HR / People
1
🧠 ML / AI
1
Poolside — 12 jobs
💻 Engineering
9
📊 Data
2
🧠 ML / AI
1
Summary
Hebbia scores 4.4/5.0 on Glassdoor with a 3.2 work-life balance rating. Poolside scores 3.8/5.0 overall with a 3.5 WLB. That’s a 0.6-point gap on overall satisfaction.
Both companies share these culture values: Engineering-Driven, Learning & Growth, Wears Many Hats. Hebbia also emphasizes Ship Fast & Iterate, Direct Product Impact. Poolside also emphasizes Remote-Friendly, Flat Hierarchy.
On the hiring front, Hebbia has 32 open roles and Poolside has 12 open roles.