Pylon
Small (~70)
Tailscale
Small (~290)
Best For
Pylon
Best for: Early-career engineers who want YC-style startup intensity and direct product ownership at a small, fast-moving team
Tailscale
Best for: Systems engineers who value location-equal pay, generous parental leave, and working on deeply technical networking problems
Ratings
PylonTailscale
3.0
4.4
Overall
3.5
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 (Marty Kausas)
👍 88% Recommend
👤 92% CEO Approval (Avery Pennarun)
Culture Values
Pylon only
🚀 Ship Fast & Iterate🧩 Wears Many Hats🎯 Direct Product Impact
Tailscale only
🌐 Remote-Friendly⚖️ Work-Life Balance💎 Strong Comp & Equity⚙️ Engineering-Driven🌈 Diverse & Inclusive🪟 Transparent
Shared
None
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
Small YC + a16z-backed team with strong product-market fit in B2B support — but polarized Glassdoor reviews flag an aggressive culture and minimal processes.
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
Pylon — 31 jobs
💼 Sales / GTM
11
💻 Engineering
10
🎨 Design
3
📣 Marketing
2
👤 HR / People
1
📋 Product
1
Tailscale — 52 jobs
💻 Engineering
25
💼 Sales / GTM
11
⚙️ Operations
4
📋 Product
4
📊 Data
2
🎨 Design
2
📣 Marketing
2
Summary
Pylon scores 3.0/5.0 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 1.4-point gap on overall satisfaction.
On the hiring front, Pylon has 31 open roles and Tailscale has 52 open roles.