Hebbia
Small (~140)
Sierra
Large (~500)
Best For
Hebbia
Best for: Engineers who want a famously kind, high-EQ team building cutting-edge AI for finance and legal professionals
Sierra
Best for: Builders who want to work with proven Salesforce and Google leadership on enterprise AI agents
Ratings
HebbiaSierra
4.4
4.0
Overall
3.2
3.5
Work-Life Balance
4.5
4.1
Culture & Values
4.4
4.0
Comp & Benefits
4.2
3.8
Senior Mgmt
4.2
3.8
Career Opps
👍 88% Recommend
👤 92% CEO Approval (George Sivulka)
👍 80% Recommend
👤 84% CEO Approval (Bret Taylor)
Culture Values
Hebbia only
🧩 Wears Many Hats🎯 Direct Product Impact
Sierra only
💎 Strong Comp & Equity
Shared
⚙️ Engineering-Driven🚀 Ship Fast & Iterate🌱 Learning & Growth
Pros & Cons
Hebbia
- Incredible culture and smart, kind team
- Cutting-edge AI work in finance
- Very long hours expected
- Fully in-office, no flexibility
Sierra
- Elite founders with proven track records
- Strong equity at $10B valuation
- In-person-first culture
- Competitive intensity may not suit everyone
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.
Sierra
Choose Sierra if you want elite founders (Bret Taylor, Clay Bavor) and strong equity at a $10B enterprise AI company — but it's in-person-first and the competitive intensity won't suit everyone.
Open Roles
Hebbia — 32 jobs
💼 Sales / GTM
10
💻 Engineering
8
📊 Data
2
🎨 Design
2
💰 Finance
1
👤 HR / People
1
🧠 ML / AI
1
Sierra — 134 jobs
💻 Engineering
42
💼 Sales / GTM
27
📋 Product
15
👤 HR / People
7
🎨 Design
5
⚖️ Legal
5
📣 Marketing
5
⚙️ Operations
5
📊 Data
2
💰 Finance
1
Summary
Hebbia scores 4.4/5.0 on Glassdoor with a 3.2 work-life balance rating. Sierra scores 4.0/5.0 overall with a 3.5 WLB. That’s a 0.4-point gap on overall satisfaction.
Both companies share these culture values: Engineering-Driven, Ship Fast & Iterate, Learning & Growth. Hebbia also emphasizes Wears Many Hats, Direct Product Impact. Sierra also emphasizes Strong Comp & Equity.
On the hiring front, Hebbia has 32 open roles and Sierra has 134 open roles.