Pylon
Small (~70)
Tailscale
Small (~290)
Best For
Pylon
Best for: Professionals interested in Pylon
Tailscale
Best for: Professionals interested in Tailscale
Ratings
PylonTailscale
3.0
4.4
Overall
4.0
4.5
Work-Life Balance
3.1
4.5
Culture & Values
3.0
4.4
Comp & Benefits
2.8
4.2
Senior Mgmt
2.8
4.2
Career Opps
👍 60% Recommend
👤 63% CEO Approval (CEO)
👍 88% Recommend
👤 92% CEO Approval (CEO)
Culture Values
Pylon only
🚀 Ship Fast & Iterate🤝 Flat Hierarchy🧩 Wears Many Hats🎯 Direct Product Impact
Tailscale only
🌐 Remote-Friendly⚖️ Work-Life Balance💎 Strong Comp & Equity🌈 Diverse & Inclusive🪟 Transparent
Shared
⚙️ Engineering-Driven
Pros & Cons
Pylon
- YC + a16z backed with strong product-market fit in B2B customer support
- Small team with outsized ownership — every engineer directly shapes the product
- Polarized reviews — aggressive culture reported by some employees
- Very early-stage with minimal processes — only 4 Glassdoor reviews
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
Pylon
Pylon — check Glassdoor for detailed reviews.
Tailscale
Tailscale — check Glassdoor for detailed reviews.
Open Roles
Pylon — 29 jobs
💼 Sales / GTM
12
💻 Engineering
9
🎨 Design
2
📣 Marketing
2
💰 Finance
1
📋 Product
1
Tailscale — 36 jobs
💻 Engineering
25
📋 Product
4
📊 Data
2
📣 Marketing
2
💼 Sales / GTM
1