Hebbia
Small (~140)
Twilio
Large (~5,500)
Best For
Hebbia
Best for: Engineers who want a famously kind, high-EQ team building cutting-edge AI for finance and legal professionals
Twilio
Best for: Professionals interested in Twilio
Ratings
HebbiaTwilio
4.4
3.9
Overall
3.2
4.1
Work-Life Balance
4.5
4.0
Culture & Values
4.4
3.9
Comp & Benefits
4.2
3.7
Senior Mgmt
4.2
3.7
Career Opps
👍 88% Recommend
👤 92% CEO Approval (George Sivulka)
👍 78% Recommend
👤 82% CEO Approval (CEO)
Culture Values
Hebbia only
🚀 Ship Fast & Iterate🧩 Wears Many Hats🎯 Direct Product Impact
Twilio only
🌐 Remote-Friendly⚖️ Work-Life Balance🔓 Open Source💎 Strong Comp & Equity
Shared
⚙️ Engineering-Driven🌱 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
Twilio
- Genuine remote-first flexibility with excellent work-life balance
- Strong compensation, benefits, and engineering-driven culture
- Frequent reorgs and leadership changes create uncertainty
- Culture has shifted from creative builders to more corporate, profit-driven focus
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.
Twilio
Twilio — check Glassdoor for detailed reviews.
Open Roles
Hebbia — 32 jobs
💼 Sales / GTM
10
💻 Engineering
8
📊 Data
2
🎨 Design
2
💰 Finance
1
👤 HR / People
1
🧠 ML / AI
1
Twilio — 143 jobs
💼 Sales / GTM
44
💻 Engineering
43
📋 Product
8
🧠 ML / AI
7
📣 Marketing
6
⚙️ Operations
3
📊 Data
2
🎨 Design
2
💰 Finance
2
👤 HR / People
2
⚖️ Legal
2
Summary
Hebbia scores 4.4/5.0 on Glassdoor with a 3.2 work-life balance rating. Twilio scores 3.9/5.0 overall with a 4.1 WLB. That’s a 0.5-point gap on overall satisfaction.
Both companies share these culture values: Engineering-Driven, Learning & Growth. Hebbia also emphasizes Ship Fast & Iterate, Wears Many Hats, Direct Product Impact. Twilio also emphasizes Remote-Friendly, Work-Life Balance, Open Source, Strong Comp & Equity.
On the hiring front, Hebbia has 32 open roles and Twilio has 143 open roles.