Cloudflare
Large (~4,000)
Tailscale
Small (~290)
Best For
Cloudflare
Best for: Engineers who want mission-driven work building critical internet infrastructure
Tailscale
Best for: Professionals interested in Tailscale
Ratings
CloudflareTailscale
3.9
4.4
Overall
3.7
4.5
Work-Life Balance
4.0
4.5
Culture & Values
3.8
4.4
Comp & Benefits
3.5
4.2
Senior Mgmt
3.8
4.2
Career Opps
👍 72% Recommend
👤 77% CEO Approval (Matthew Prince)
👍 88% Recommend
👤 92% CEO Approval (CEO)
Culture Values
Cloudflare only
🚀 Ship Fast & Iterate🎯 Direct Product Impact🌱 Learning & Growth
Tailscale only
🌐 Remote-Friendly⚖️ Work-Life Balance💎 Strong Comp & Equity🌈 Diverse & Inclusive
Shared
⚙️ Engineering-Driven🪟 Transparent
Pros & Cons
Cloudflare
- Mission-driven company building critical internet infrastructure — meaningful work with real impact
- Smart colleagues and a culture that values innovation, shipping quickly, and technical excellence
- Compensation can lag behind FAANG competitors, especially base salary
- Some teams experience high pressure and demanding workloads with uneven management quality
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
Cloudflare
Choose Cloudflare if you want mission-driven work building critical internet infrastructure with sharp engineers — but compensation lags FAANG and pressure can be high.
Tailscale
Tailscale — check Glassdoor for detailed reviews.
Open Roles
Cloudflare — 533 jobs
💼 Sales / GTM
250
💻 Engineering
151
📋 Product
26
📣 Marketing
13
📊 Data
12
👤 HR / People
8
⚙️ Operations
5
⚖️ Legal
4
🧠 ML / AI
4
🎨 Design
2
💰 Finance
2
Tailscale — 44 jobs
💻 Engineering
25
📋 Product
6
💼 Sales / GTM
5
📊 Data
2
📣 Marketing
2
⚙️ Operations
2
Summary
Cloudflare 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, Transparent. Cloudflare also emphasizes Ship Fast & Iterate, Direct Product Impact, Learning & Growth. Tailscale also emphasizes Remote-Friendly, Work-Life Balance, Strong Comp & Equity, Diverse & Inclusive.
On the hiring front, Cloudflare has 533 open roles and Tailscale has 44 open roles.