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: Professionals interested in Tailscale
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 (CEO)
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
Tailscale — check Glassdoor for detailed reviews.
Open Roles
Airbnb — 243 jobs
💻 Engineering
63
🎧 Support
26
📊 Data
14
🧠 ML / AI
12
📣 Marketing
11
📋 Product
11
💼 Sales / GTM
11
⚖️ Legal
6
⚙️ Operations
6
🎨 Design
2
💰 Finance
2
👤 HR / People
2
Tailscale — 36 jobs
💻 Engineering
25
📋 Product
4
📊 Data
2
📣 Marketing
2
💼 Sales / GTM
1