Decagon
Small (~210)
Hebbia
Small (~140)
Best For
Decagon
Best for: Builders who want to ship AI customer support agents directly to F500 customers with technical founders deeply involved
Hebbia
Best for: Engineers who want a famously kind, high-EQ team building cutting-edge AI for finance and legal professionals
Ratings
DecagonHebbia
3.9
4.4
Overall
3.7
3.2
Work-Life Balance
3.8
4.5
Culture & Values
3.2
4.4
Comp & Benefits
3.7
4.2
Senior Mgmt
3.7
4.2
Career Opps
👍 75% Recommend
👤 85% CEO Approval (Jesse Zhang)
👍 88% Recommend
👤 92% CEO Approval (George Sivulka)
Culture Values
Decagon only
💎 Strong Comp & Equity
Hebbia only
🌱 Learning & Growth🧩 Wears Many Hats
Shared
⚙️ Engineering-Driven🚀 Ship Fast & Iterate🎯 Direct Product Impact
Pros & Cons
Decagon
- Strong engineering-driven culture with technical founders still deeply involved
- Ship meaningful AI features to enterprise customers every week
- Intense workload and high expectations — not a typical 40-hour week
- SF-centric; most roles expect in-office presence
Hebbia
- Incredible culture and smart, kind team
- Cutting-edge AI work in finance
- Very long hours expected
- Fully in-office, no flexibility
Bottom Line
Decagon
Choose Decagon if you want intense builder energy at a $4.5B Series D AI agents startup with real enterprise revenue — but expect SF office-centric culture and cash comp that trails top AI labs.
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
Decagon — 95 jobs
💼 Sales / GTM
32
💻 Engineering
25
📋 Product
7
🧠 ML / AI
6
⚙️ Operations
3
⚖️ Legal
2
📣 Marketing
2
📊 Data
1
🎨 Design
1
👤 HR / People
1
Hebbia — 32 jobs
💼 Sales / GTM
10
💻 Engineering
8
📊 Data
2
🎨 Design
2
💰 Finance
1
👤 HR / People
1
🧠 ML / AI
1
Summary
Decagon 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. Decagon also emphasizes Strong Comp & Equity. Hebbia also emphasizes Learning & Growth, Wears Many Hats.
On the hiring front, Decagon has 95 open roles and Hebbia has 32 open roles.