Tailscale
Small (~290)
Vast AI
Small (~30)
Best For
Tailscale
Best for: Systems engineers who value location-equal pay, generous parental leave, and working on deeply technical networking problems
Vast AI
Best for: Scrappy generalists who want a front-row seat to the AI compute revolution
Ratings
TailscaleVast AI
4.4
5.0
Overall
4.5
3.8
Work-Life Balance
4.5
5.0
Culture & Values
4.4
5.0
Comp & Benefits
4.2
5.0
Senior Mgmt
4.2
5.0
Career Opps
👍 88% Recommend
👤 92% CEO Approval (Avery Pennarun)
👍 100% Recommend
👤 100% CEO Approval (Jake Cannell)
Culture Values
Tailscale only
🌐 Remote-Friendly⚖️ Work-Life Balance🌈 Diverse & Inclusive🪟 Transparent
Vast AI only
🚀 Ship Fast & Iterate🤝 Flat Hierarchy🧩 Wears Many Hats
Shared
💎 Strong Comp & Equity⚙️ Engineering-Driven
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
Vast AI
- Front-row seat to the AI compute revolution — demand for GPU cloud is surging
- Strong compensation and generous equity stakes for a bootstrapped startup
- Processes are still being defined — expect ad hoc workflows
- Intense workload — the team explicitly values high output
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.
Vast AI
Choose Vast AI if you want perfect Glassdoor scores and generous equity at a tiny GPU marketplace — but expect startup chaos.
Open Roles
Tailscale — 52 jobs
💻 Engineering
25
💼 Sales / GTM
11
⚙️ Operations
4
📋 Product
4
📊 Data
2
🎨 Design
2
📣 Marketing
2
Vast AI — 9 jobs
💻 Engineering
6
🧠 ML / AI
2
Summary
Tailscale scores 4.4/5.0 on Glassdoor with a 4.5 work-life balance rating. Vast AI scores 5.0/5.0 overall with a 3.8 WLB. That’s a 0.6-point gap on overall satisfaction.
Both companies share these culture values: Strong Comp & Equity, Engineering-Driven. Tailscale also emphasizes Remote-Friendly, Work-Life Balance, Diverse & Inclusive, Transparent. Vast AI also emphasizes Ship Fast & Iterate, Flat Hierarchy, Wears Many Hats.
On the hiring front, Tailscale has 52 open roles and Vast AI has 9 open roles.