Tailscale
Small (~290)
Vast AI
Small (~30)
Best For
Tailscale
Best for: Professionals interested in Tailscale
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
4.5
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 (CEO)
👍 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
Tailscale — check Glassdoor for detailed reviews.
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 — 36 jobs
💻 Engineering
25
📋 Product
4
📊 Data
2
📣 Marketing
2
💼 Sales / GTM
1
Vast AI — 10 jobs
💻 Engineering
5
🧠 ML / AI
2
📊 Data
1