Tailscale
Small (~290)
Vanta
Large (~1,400)
Best For
Tailscale
Best for: Systems engineers who value location-equal pay, generous parental leave, and working on deeply technical networking problems
Vanta
Best for: Engineers and salespeople who want top-of-market comp at the category leader in security compliance and can handle a meeting-heavy, high-intensity pace
Ratings
TailscaleVanta
4.4
3.8
Overall
4.5
3.3
Work-Life Balance
4.5
3.9
Culture & Values
4.4
3.8
Comp & Benefits
4.2
3.6
Senior Mgmt
4.2
3.6
Career Opps
👍 88% Recommend
👤 92% CEO Approval (Avery Pennarun)
👍 76% Recommend
👤 80% CEO Approval (Christina Cacioppo)
Culture Values
Tailscale only
🌐 Remote-Friendly⚖️ Work-Life Balance⚙️ Engineering-Driven🌈 Diverse & Inclusive🪟 Transparent
Vanta only
🎯 Direct Product Impact🚀 Ship Fast & Iterate
Shared
💎 Strong Comp & Equity
Pros & Cons
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
Vanta
- Strong compensation rated 4.3/5 — best category score
- Market-defining product in security compliance automation
- Brutal meeting culture pushing work into nights and weekends
- Virtually no AEs hit quota — targets unrealistically high
Bottom Line
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.
Vanta
Pays extremely well and owns its market niche, but the meeting-heavy culture and low WLB score (3.3/5) signal this is not for anyone seeking balance.
Open Roles
Tailscale — 44 jobs
💻 Engineering
25
📋 Product
6
💼 Sales / GTM
5
📊 Data
2
📣 Marketing
2
⚙️ Operations
2
Vanta — 169 jobs
💼 Sales / GTM
73
💻 Engineering
50
📋 Product
9
🎨 Design
7
📣 Marketing
5
📊 Data
4
⚙️ Operations
2
👤 HR / People
1
⚖️ Legal
1
Summary
Tailscale scores 4.4/5.0 on Glassdoor with a 4.5 work-life balance rating. Vanta scores 3.8/5.0 overall with a 3.3 WLB. That’s a 0.6-point gap on overall satisfaction.
Both companies share these culture values: Strong Comp & Equity. Tailscale also emphasizes Remote-Friendly, Work-Life Balance, Engineering-Driven, Diverse & Inclusive, Transparent. Vanta also emphasizes Direct Product Impact, Ship Fast & Iterate.
On the hiring front, Tailscale has 44 open roles and Vanta has 169 open roles.