Decagon
Small (~210)
Tailscale
Small (~290)
Best For
Decagon
Best for: Builders who want to ship AI customer support agents directly to F500 customers with technical founders deeply involved
Tailscale
Best for: Systems engineers who value location-equal pay, generous parental leave, and working on deeply technical networking problems
Ratings
DecagonTailscale
3.9
4.4
Overall
3.7
4.5
Work-Life Balance
3.8
4.5
Culture & Values
3.2
4.4
Comp & Benefits
3.7
4.2
Senior Mgmt
3.7
4.2
Career Opps
👍 75% Recommend
👤 85% CEO Approval (Jesse Zhang)
👍 88% Recommend
👤 92% CEO Approval (Avery Pennarun)
Culture Values
Decagon only
🚀 Ship Fast & Iterate🎯 Direct Product Impact
Tailscale only
🌐 Remote-Friendly⚖️ Work-Life Balance🌈 Diverse & Inclusive🪟 Transparent
Shared
⚙️ Engineering-Driven💎 Strong Comp & Equity
Pros & Cons
Decagon
- Strong engineering-driven culture with technical founders still deeply involved
- Ship meaningful AI features to enterprise customers every week
- Intense workload and high expectations — not a typical 40-hour week
- SF-centric; most roles expect in-office presence
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
Decagon
Choose Decagon if you want intense builder energy at a $4.5B Series D AI agents startup with real enterprise revenue — but expect SF office-centric culture and cash comp that trails top AI labs.
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
Decagon — 95 jobs
💼 Sales / GTM
32
💻 Engineering
25
📋 Product
7
🧠 ML / AI
6
⚙️ Operations
3
⚖️ Legal
2
📣 Marketing
2
📊 Data
1
🎨 Design
1
👤 HR / People
1
Tailscale — 52 jobs
💻 Engineering
25
💼 Sales / GTM
11
⚙️ Operations
4
📋 Product
4
📊 Data
2
🎨 Design
2
📣 Marketing
2
Summary
Decagon scores 3.9/5.0 on Glassdoor with a 3.7 work-life balance rating. Tailscale scores 4.4/5.0 overall with a 4.5 WLB. That’s a 0.5-point gap on overall satisfaction.
Both companies share these culture values: Engineering-Driven, Strong Comp & Equity. Decagon also emphasizes Ship Fast & Iterate, Direct Product Impact. Tailscale also emphasizes Remote-Friendly, Work-Life Balance, Diverse & Inclusive, Transparent.
On the hiring front, Decagon has 95 open roles and Tailscale has 52 open roles.