Navan
Large (~3,500)
Tailscale
Small (~290)
Best For
Navan
Best for: Professionals interested in Navan
Tailscale
Best for: Systems engineers who value location-equal pay, generous parental leave, and working on deeply technical networking problems
Ratings
NavanTailscale
4.0
4.4
Overall
3.7
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 (CEO)
👍 88% Recommend
👤 92% CEO Approval (Avery Pennarun)
Culture Values
Navan only
🚀 Ship Fast & Iterate🌱 Learning & Growth🎯 Direct Product Impact
Tailscale only
🌐 Remote-Friendly⚖️ Work-Life Balance🌈 Diverse & Inclusive🪟 Transparent
Shared
💎 Strong Comp & Equity⚙️ Engineering-Driven
Pros & Cons
Navan
- Strong career growth with managers who genuinely invest in your development
- AI-driven product with real market traction and meaningful work impact
- Frequent organizational shifts require high adaptability and resilience
- Intense workload with ambitious targets — pace isn't for 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
Navan
Navan — check Glassdoor for detailed reviews.
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
Navan — 206 jobs
💼 Sales / GTM
66
💻 Engineering
34
⚙️ Operations
9
📋 Product
7
⚖️ Legal
6
💰 Finance
4
👤 HR / People
3
📣 Marketing
3
📊 Data
1
🎨 Design
1
🧠 ML / AI
1
Tailscale — 52 jobs
💻 Engineering
25
💼 Sales / GTM
11
⚙️ Operations
4
📋 Product
4
📊 Data
2
🎨 Design
2
📣 Marketing
2
Summary
Navan scores 4.0/5.0 on Glassdoor with a 3.7 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: Strong Comp & Equity, Engineering-Driven. Navan also emphasizes Ship Fast & Iterate, Learning & Growth, Direct Product Impact. Tailscale also emphasizes Remote-Friendly, Work-Life Balance, Diverse & Inclusive, Transparent.
On the hiring front, Navan has 206 open roles and Tailscale has 52 open roles.