Tailscale
Small (~290)
Writer
Mid (~400)
Best For
Tailscale
Best for: Systems engineers who value location-equal pay, generous parental leave, and working on deeply technical networking problems
Writer
Best for: Professionals interested in Writer
Ratings
TailscaleWriter
4.4
3.5
Overall
4.5
2.7
Work-Life Balance
4.5
3.6
Culture & Values
4.4
3.5
Comp & Benefits
4.2
3.3
Senior Mgmt
4.2
3.3
Career Opps
👍 88% Recommend
👤 92% CEO Approval (Avery Pennarun)
👍 70% Recommend
👤 74% CEO Approval (CEO)
Culture Values
Tailscale only
🌐 Remote-Friendly⚖️ Work-Life Balance💎 Strong Comp & Equity🌈 Diverse & Inclusive🪟 Transparent
Writer only
🚀 Ship Fast & Iterate🔓 Open Source
Shared
⚙️ 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
Writer
- Real AI engineering with proprietary LLMs — not just wrapping OpenAI APIs
- Strong enterprise traction and visionary product direction
- Intense work culture with very high expectations and limited work-life balance
- Growing management layers creating organizational friction
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.
Writer
Writer — check Glassdoor for detailed reviews.
Open Roles
Tailscale — 52 jobs
💻 Engineering
25
💼 Sales / GTM
11
⚙️ Operations
4
📋 Product
4
📊 Data
2
🎨 Design
2
📣 Marketing
2
Writer — 49 jobs
💻 Engineering
16
💼 Sales / GTM
12
🎨 Design
1
⚙️ Operations
1
📋 Product
1
Summary
Tailscale scores 4.4/5.0 on Glassdoor with a 4.5 work-life balance rating. Writer scores 3.5/5.0 overall with a 2.7 WLB. That’s a 0.9-point gap on overall satisfaction.
Both companies share these culture values: Engineering-Driven. Tailscale also emphasizes Remote-Friendly, Work-Life Balance, Strong Comp & Equity, Diverse & Inclusive, Transparent. Writer also emphasizes Ship Fast & Iterate, Open Source.
On the hiring front, Tailscale has 52 open roles and Writer has 49 open roles.