Hebbia
Small (~140)
OpenAI
Large (~3,500)
Best For
Hebbia
Best for: Engineers who want a famously kind, high-EQ team building cutting-edge AI for finance and legal professionals
OpenAI
Best for: Engineers who want to build frontier AI models at the company defining the industry, with elite compensation
Ratings
HebbiaOpenAI
4.4
4.5
Overall
3.2
3.6
Work-Life Balance
4.5
4.6
Culture & Values
4.4
4.5
Comp & Benefits
4.2
4.3
Senior Mgmt
4.2
4.3
Career Opps
👍 88% Recommend
👤 92% CEO Approval (George Sivulka)
👍 90% Recommend
👤 95% CEO Approval (Sam Altman)
Culture Values
Hebbia only
🧩 Wears Many Hats
OpenAI only
💎 Strong Comp & Equity
Shared
⚙️ Engineering-Driven🚀 Ship Fast & Iterate🌱 Learning & Growth🎯 Direct Product Impact
Pros & Cons
Hebbia
- Incredible culture and smart, kind team
- Cutting-edge AI work in finance
- Very long hours expected
- Fully in-office, no flexibility
OpenAI
- Cutting-edge frontier AI research with world-class colleagues
- Elite compensation — top-tier TC and equity packages
- High-intensity environment — long hours and intense pace are the norm
- Internal politics and rapid org changes as the company scales
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.
OpenAI
High-intensity, mission-driven culture with world-class colleagues and top-tier comp — but expect long hours, rapid org changes, and internal politics as the company scales.
Open Roles
Hebbia — 32 jobs
💼 Sales / GTM
10
💻 Engineering
8
📊 Data
2
🎨 Design
2
💰 Finance
1
👤 HR / People
1
🧠 ML / AI
1
OpenAI — 655 jobs
💻 Engineering
317
💼 Sales / GTM
57
📋 Product
30
📊 Data
28
🧠 ML / AI
28
📣 Marketing
24
⚙️ Operations
17
⚖️ Legal
13
🎨 Design
10
👤 HR / People
9
💰 Finance
7
🎧 Support
4
Summary
Hebbia scores 4.4/5.0 on Glassdoor with a 3.2 work-life balance rating. OpenAI scores 4.5/5.0 overall with a 3.6 WLB. That’s a 0.1-point gap on overall satisfaction.
Both companies share these culture values: Engineering-Driven, Ship Fast & Iterate, Learning & Growth, Direct Product Impact. Hebbia also emphasizes Wears Many Hats. OpenAI also emphasizes Strong Comp & Equity.
On the hiring front, Hebbia has 32 open roles and OpenAI has 655 open roles.