Hebbia
Small (~140)
HubSpot
Large (~8,000)
Best For
Hebbia
Best for: Engineers who want a famously kind, high-EQ team building cutting-edge AI for finance and legal professionals
HubSpot
Best for: People who prioritize genuine work-life balance and a transparent, inclusive culture
Ratings
HebbiaHubSpot
4.4
4.3
Overall
3.2
4.1
Work-Life Balance
4.5
4.5
Culture & Values
4.4
3.9
Comp & Benefits
4.2
4.1
Senior Mgmt
4.2
4.0
Career Opps
👍 88% Recommend
👤 92% CEO Approval (George Sivulka)
👍 87% Recommend
👤 92% CEO Approval (Yamini Rangan)
Culture Values
Hebbia only
⚙️ Engineering-Driven🚀 Ship Fast & Iterate🧩 Wears Many Hats🎯 Direct Product Impact
HubSpot only
🌈 Diverse & Inclusive⚖️ Work-Life Balance🪟 Transparent🕐 Flexible Hours🛡️ Safe to Fail
Shared
🌱 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
HubSpot
- Culture Code is legendary — transparency, autonomy, flexibility are real
- Remote-first done right with genuine work-life balance
- Enterprise sales culture can clash with engineering
- Comp below FAANG for senior roles
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.
HubSpot
Choose HubSpot if you want legendary culture with real flexibility and psychological safety — but comp is below FAANG.
Open Roles
Hebbia — 32 jobs
💼 Sales / GTM
10
💻 Engineering
8
📊 Data
2
🎨 Design
2
💰 Finance
1
👤 HR / People
1
🧠 ML / AI
1
HubSpot — 191 jobs
💼 Sales / GTM
131
💻 Engineering
25
📊 Data
3
🎨 Design
3
🎧 Support
3
⚖️ Legal
2
🧠 ML / AI
2
📋 Product
2
💰 Finance
1
👤 HR / People
1
⚙️ Operations
1
Summary
Hebbia scores 4.4/5.0 on Glassdoor with a 3.2 work-life balance rating. HubSpot scores 4.3/5.0 overall with a 4.1 WLB. That’s a 0.1-point gap on overall satisfaction.
Both companies share these culture values: Learning & Growth. Hebbia also emphasizes Engineering-Driven, Ship Fast & Iterate, Wears Many Hats, Direct Product Impact. HubSpot also emphasizes Diverse & Inclusive, Work-Life Balance, Transparent, Flexible Hours, Safe to Fail.
On the hiring front, Hebbia has 32 open roles and HubSpot has 191 open roles.