Hebbia
Small (~140)
Tailscale
Small (~290)
Best For
Hebbia
Best for: Engineers who want a famously kind, high-EQ team building cutting-edge AI for finance and legal professionals
Tailscale
Best for: Systems engineers who value location-equal pay, generous parental leave, and working on deeply technical networking problems
Ratings
HebbiaTailscale
4.4
4.4
Overall
3.2
4.5
Work-Life Balance
4.5
4.5
Culture & Values
4.4
4.4
Comp & Benefits
4.2
4.2
Senior Mgmt
4.2
4.2
Career Opps
👍 88% Recommend
👤 92% CEO Approval (George Sivulka)
👍 88% Recommend
👤 92% CEO Approval (Avery Pennarun)
Culture Values
Hebbia only
🚀 Ship Fast & Iterate🌱 Learning & Growth🧩 Wears Many Hats🎯 Direct Product Impact
Tailscale only
🌐 Remote-Friendly⚖️ Work-Life Balance💎 Strong Comp & Equity🌈 Diverse & Inclusive🪟 Transparent
Shared
⚙️ Engineering-Driven
Pros & Cons
Hebbia
- Incredible culture and smart, kind team
- Cutting-edge AI work in finance
- Very long hours expected
- Fully in-office, no flexibility
Tailscale
- Same pay worldwide with 26 weeks parental leave and genuine work-life balance
- Brilliant, nerdy CEO who deeply understands the tech — culture is intellectual and respectful
- Career progression limited — only 3.0/5 on career opportunities
- Middle management still developing — some growing pains as the org 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.
Tailscale
Intellectual, engineer-led culture with same pay worldwide and 26 weeks parental leave — but career progression is limited and middle management is still maturing.
Open Roles
Hebbia — 32 jobs
💼 Sales / GTM
10
💻 Engineering
8
📊 Data
2
🎨 Design
2
💰 Finance
1
👤 HR / People
1
🧠 ML / AI
1
Tailscale — 52 jobs
💻 Engineering
25
💼 Sales / GTM
11
⚙️ Operations
4
📋 Product
4
📊 Data
2
🎨 Design
2
📣 Marketing
2
Summary
Hebbia scores 4.4/5.0 on Glassdoor with a 3.2 work-life balance rating. Tailscale scores 4.4/5.0 overall with a 4.5 WLB. They’re tied on overall satisfaction.
Both companies share these culture values: Engineering-Driven. Hebbia also emphasizes Ship Fast & Iterate, Learning & Growth, Wears Many Hats, Direct Product Impact. Tailscale also emphasizes Remote-Friendly, Work-Life Balance, Strong Comp & Equity, Diverse & Inclusive, Transparent.
On the hiring front, Hebbia has 32 open roles and Tailscale has 52 open roles.