Airbnb
Large (~7,300)
Sierra
Large (~500)
Best For
Airbnb
Best for: Engineers who want Live Anywhere flexibility with strong comp and no pay cuts
Sierra
Best for: Builders who want to work with proven Salesforce and Google leadership on enterprise AI agents
Ratings
AirbnbSierra
4.1
4.0
Overall
4.0
3.5
Work-Life Balance
4.2
4.1
Culture & Values
4.2
4.0
Comp & Benefits
3.5
3.8
Senior Mgmt
3.5
3.8
Career Opps
👍 80% Recommend
👤 87% CEO Approval (Brian Chesky)
👍 80% Recommend
👤 84% CEO Approval (Bret Taylor)
Culture Values
Airbnb only
🌐 Remote-Friendly⚖️ Work-Life Balance🌈 Diverse & Inclusive🔓 Open Source
Sierra only
⚙️ Engineering-Driven🚀 Ship Fast & Iterate🌱 Learning & Growth
Shared
💎 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
Sierra
- Elite founders with proven track records
- Strong equity at $10B valuation
- In-person-first culture
- Competitive intensity may not suit everyone
Bottom Line
Airbnb
Choose Airbnb if you want genuine remote flexibility and travel perks — but promotions are slow and bureaucracy is growing.
Sierra
Choose Sierra if you want elite founders (Bret Taylor, Clay Bavor) and strong equity at a $10B enterprise AI company — but it's in-person-first and the competitive intensity won't suit everyone.
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
Sierra — 134 jobs
💻 Engineering
42
💼 Sales / GTM
27
📋 Product
15
👤 HR / People
7
🎨 Design
5
⚖️ Legal
5
📣 Marketing
5
⚙️ Operations
5
📊 Data
2
💰 Finance
1
Summary
Airbnb scores 4.1/5.0 on Glassdoor with a 4.0 work-life balance rating. Sierra scores 4.0/5.0 overall with a 3.5 WLB. That’s a 0.1-point gap on overall satisfaction.
Both companies share these culture values: Strong Comp & Equity. Airbnb also emphasizes Remote-Friendly, Work-Life Balance, Diverse & Inclusive, Open Source. Sierra also emphasizes Engineering-Driven, Ship Fast & Iterate, Learning & Growth.
On the hiring front, Airbnb has 244 open roles and Sierra has 134 open roles.