Sierra
Large (~500)
Tailscale
Small (~290)
Best For
Sierra
Best for: Builders who want to work with proven Salesforce and Google leadership on enterprise AI agents
Tailscale
Best for: Systems engineers who value location-equal pay, generous parental leave, and working on deeply technical networking problems
Ratings
SierraTailscale
4.0
4.4
Overall
3.5
4.5
Work-Life Balance
4.1
4.5
Culture & Values
4.0
4.4
Comp & Benefits
3.8
4.2
Senior Mgmt
3.8
4.2
Career Opps
👍 80% Recommend
👤 84% CEO Approval (Bret Taylor)
👍 88% Recommend
👤 92% CEO Approval (Avery Pennarun)
Culture Values
Sierra only
🚀 Ship Fast & Iterate🌱 Learning & Growth
Tailscale only
🌐 Remote-Friendly⚖️ Work-Life Balance🌈 Diverse & Inclusive🪟 Transparent
Shared
⚙️ Engineering-Driven💎 Strong Comp & Equity
Pros & Cons
Sierra
- Elite founders with proven track records
- Strong equity at $10B valuation
- In-person-first culture
- Competitive intensity may not suit everyone
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
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.
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
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
Tailscale — 52 jobs
💻 Engineering
25
💼 Sales / GTM
11
⚙️ Operations
4
📋 Product
4
📊 Data
2
🎨 Design
2
📣 Marketing
2
Summary
Sierra scores 4.0/5.0 on Glassdoor with a 3.5 work-life balance rating. Tailscale scores 4.4/5.0 overall with a 4.5 WLB. That’s a 0.4-point gap on overall satisfaction.
Both companies share these culture values: Engineering-Driven, Strong Comp & Equity. Sierra also emphasizes Ship Fast & Iterate, Learning & Growth. Tailscale also emphasizes Remote-Friendly, Work-Life Balance, Diverse & Inclusive, Transparent.
On the hiring front, Sierra has 134 open roles and Tailscale has 52 open roles.