Cursor (Anysphere)
Small (~50)
Tailscale
Small (~290)
Best For
Cursor (Anysphere)
Best for: Generalist engineers who want extreme ownership at the most-loved AI code editor
Tailscale
Best for: Professionals interested in Tailscale
Ratings
Cursor (Anysphere)Tailscale
4.0
4.4
Overall
3.5
4.5
Work-Life Balance
4.0
4.5
Culture & Values
4.2
4.4
Comp & Benefits
3.8
4.2
Senior Mgmt
3.5
4.2
Career Opps
👍 85% Recommend
👤 90% CEO Approval (Michael Truell)
👍 88% Recommend
👤 92% CEO Approval (CEO)
Culture Values
Cursor (Anysphere) only
🚀 Ship Fast & Iterate🎯 Direct Product Impact🤝 Flat Hierarchy🧩 Wears Many Hats
Tailscale only
🌐 Remote-Friendly⚖️ Work-Life Balance💎 Strong Comp & Equity🌈 Diverse & Inclusive🪟 Transparent
Shared
⚙️ Engineering-Driven
Pros & Cons
Cursor (Anysphere)
- Building the most-loved AI code editor — massive developer love and daily impact
- Tiny team, extreme ownership — every person shapes the product directly
- Extremely small team = no specialists; everyone does everything
- Intense pace — the speed of shipping can be relentless
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
Cursor (Anysphere)
Choose Cursor if you want to shape the future of AI-assisted coding on a tiny team — but the pace is relentless.
Tailscale
Tailscale — check Glassdoor for detailed reviews.
Open Roles
Cursor (Anysphere) — 58 jobs
💼 Sales / GTM
20
💻 Engineering
19
📊 Data
4
🎨 Design
3
🧠 ML / AI
3
⚖️ Legal
2
📣 Marketing
2
👤 HR / People
1
Tailscale — 36 jobs
💻 Engineering
25
📋 Product
4
📊 Data
2
📣 Marketing
2
💼 Sales / GTM
1