Airbnb
Large (~7,300)
Tailscale
Small (~290)
Best For
Airbnb
Best for: Engineers who want Live Anywhere flexibility with strong comp and no pay cuts
Tailscale
Best for: Systems engineers who value location-equal pay, generous parental leave, and working on deeply technical networking problems
Ratings
AirbnbTailscale
4.1
4.4
Overall
4.0
4.5
Work-Life Balance
4.2
4.5
Culture & Values
4.2
4.4
Comp & Benefits
3.5
4.2
Senior Mgmt
3.5
4.2
Career Opps
👍 80% Recommend
👤 87% CEO Approval (Brian Chesky)
👍 88% Recommend
👤 92% CEO Approval (Avery Pennarun)
Culture Values
Airbnb only
🔓 Open Source
Tailscale only
⚙️ Engineering-Driven🪟 Transparent
Shared
🌐 Remote-Friendly⚖️ Work-Life Balance🌈 Diverse & Inclusive💎 Strong Comp & Equity
Pros & Cons
Airbnb
- Live and Work Anywhere policy — genuine remote flexibility with no pay cuts
- Strong compensation and benefits with quarterly travel credits and educational stipends
- Limited career growth — senior roles often filled externally, promotions are slow
- Post-IPO cultural shift — increasing bureaucracy and internal politics at mid-to-senior levels
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
Airbnb
Choose Airbnb if you want genuine remote flexibility and travel perks — but promotions are slow and bureaucracy is growing.
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
Airbnb — 244 jobs
💻 Engineering
76
📊 Data
23
📋 Product
14
🎧 Support
14
🧠 ML / AI
12
⚖️ Legal
11
⚙️ Operations
11
📣 Marketing
10
💼 Sales / GTM
9
💰 Finance
3
👤 HR / People
3
🎨 Design
2
Tailscale — 52 jobs
💻 Engineering
25
💼 Sales / GTM
11
⚙️ Operations
4
📋 Product
4
📊 Data
2
🎨 Design
2
📣 Marketing
2
Summary
Airbnb scores 4.1/5.0 on Glassdoor with a 4.0 work-life balance rating. Tailscale scores 4.4/5.0 overall with a 4.5 WLB. That’s a 0.3-point gap on overall satisfaction.
Both companies share these culture values: Remote-Friendly, Work-Life Balance, Diverse & Inclusive, Strong Comp & Equity. Airbnb also emphasizes Open Source. Tailscale also emphasizes Engineering-Driven, Transparent.
On the hiring front, Airbnb has 244 open roles and Tailscale has 52 open roles.