Notion
Mid (~800)
Tailscale
Small (~290)
Best For
Notion
Best for: Product-obsessed engineers who care deeply about craft and want to build tools that millions use daily
Tailscale
Best for: Systems engineers who value location-equal pay, generous parental leave, and working on deeply technical networking problems
Ratings
NotionTailscale
4.4
4.4
Overall
4.2
4.5
Work-Life Balance
4.5
4.5
Culture & Values
4.4
4.4
Comp & Benefits
4.2
4.2
Senior Mgmt
4.2
4.2
Career Opps
👍 88% Recommend
👤 92% CEO Approval (Ivan Zhao)
👍 88% Recommend
👤 92% CEO Approval (Avery Pennarun)
Culture Values
Notion only
🎯 Direct Product Impact🌱 Learning & Growth
Tailscale only
🌐 Remote-Friendly⚖️ Work-Life Balance
Shared
⚙️ Engineering-Driven🪟 Transparent🌈 Diverse & Inclusive💎 Strong Comp & Equity
Pros & Cons
Notion
- Incredible product culture — everyone uses Notion daily and cares deeply
- Transparent leadership with accessible founders and high trust
- Fast pace can lead to burnout, especially during product pushes
- Hybrid required (3 days in-office) — not truly remote-friendly
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
Notion
Strong product culture with a beloved CEO (96% approval) and genuine design sensibility — but hybrid-required and the pace can burn people out during product pushes.
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
Notion — 142 jobs
💼 Sales / GTM
70
💻 Engineering
18
📣 Marketing
9
📊 Data
5
👤 HR / People
4
⚙️ Operations
4
📋 Product
4
🎧 Support
4
💰 Finance
3
🎨 Design
2
⚖️ Legal
1
Tailscale — 52 jobs
💻 Engineering
25
💼 Sales / GTM
11
⚙️ Operations
4
📋 Product
4
📊 Data
2
🎨 Design
2
📣 Marketing
2
Summary
Notion scores 4.4/5.0 on Glassdoor with a 4.2 work-life balance rating. Tailscale scores 4.4/5.0 overall with a 4.5 WLB. They’re tied on overall satisfaction.
Both companies share these culture values: Engineering-Driven, Transparent, Diverse & Inclusive, Strong Comp & Equity. Notion also emphasizes Direct Product Impact, Learning & Growth. Tailscale also emphasizes Remote-Friendly, Work-Life Balance.
On the hiring front, Notion has 142 open roles and Tailscale has 52 open roles.