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: Systems engineers who value location-equal pay, generous parental leave, and working on deeply technical networking problems
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 (Avery Pennarun)
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
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
Cursor (Anysphere) — 77 jobs
💻 Engineering
33
💼 Sales / GTM
19
📊 Data
3
🧠 ML / AI
3
🎨 Design
2
👤 HR / People
2
⚖️ Legal
2
⚙️ Operations
2
📣 Marketing
1
Tailscale — 52 jobs
💻 Engineering
25
💼 Sales / GTM
11
⚙️ Operations
4
📋 Product
4
📊 Data
2
🎨 Design
2
📣 Marketing
2
Summary
Cursor (Anysphere) scores 4.0/5.0 on Glassdoor with a 3.5 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: Engineering-Driven. Cursor (Anysphere) also emphasizes Ship Fast & Iterate, Direct Product Impact, Flat Hierarchy, Wears Many Hats. Tailscale also emphasizes Remote-Friendly, Work-Life Balance, Strong Comp & Equity, Diverse & Inclusive, Transparent.
On the hiring front, Cursor (Anysphere) has 77 open roles and Tailscale has 52 open roles.