Tailscale
Small (~290)
Weaviate
Small (~110)
Best For
Tailscale
Best for: Systems engineers who value location-equal pay, generous parental leave, and working on deeply technical networking problems
Weaviate
Best for: Engineers who want open-source vector database work with true remote-first, async culture
Ratings
TailscaleWeaviate
4.4
4.3
Overall
4.5
4.2
Work-Life Balance
4.5
4.5
Culture & Values
4.4
4.0
Comp & Benefits
4.2
4.2
Senior Mgmt
4.2
4.0
Career Opps
👍 88% Recommend
👤 92% CEO Approval (Avery Pennarun)
👍 85% Recommend
👤 90% CEO Approval (Bob van Luijt)
Culture Values
Tailscale only
💎 Strong Comp & Equity⚙️ Engineering-Driven🪟 Transparent
Weaviate only
📡 Async-First🤝 Flat Hierarchy🔓 Open Source🛡️ Safe to Fail
Shared
🌐 Remote-Friendly⚖️ Work-Life Balance🌈 Diverse & Inclusive
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
Weaviate
- Excellent remote-first culture — async workflows, timezone respect, and high autonomy
- Flat, ego-free culture — your voice is heard from day 1 regardless of title
- Time zone challenges inherent to a fully distributed global team
- Startup growing pains — processes still being established, things evolve quickly
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.
Weaviate
Choose Weaviate if you want excellent remote culture with flat hierarchy and open-source mission — but expect startup growing pains.
Open Roles
Tailscale — 52 jobs
💻 Engineering
25
💼 Sales / GTM
11
⚙️ Operations
4
📋 Product
4
📊 Data
2
🎨 Design
2
📣 Marketing
2
Weaviate — 5 jobs
💻 Engineering
3
💼 Sales / GTM
2
Summary
Tailscale scores 4.4/5.0 on Glassdoor with a 4.5 work-life balance rating. Weaviate scores 4.3/5.0 overall with a 4.2 WLB. That’s a 0.1-point gap on overall satisfaction.
Both companies share these culture values: Remote-Friendly, Work-Life Balance, Diverse & Inclusive. Tailscale also emphasizes Strong Comp & Equity, Engineering-Driven, Transparent. Weaviate also emphasizes Async-First, Flat Hierarchy, Open Source, Safe to Fail.
On the hiring front, Tailscale has 52 open roles and Weaviate has 5 open roles.