Tailscale
Small (~290)
Webflow
Mid (~800)
Best For
Tailscale
Best for: Systems engineers who value location-equal pay, generous parental leave, and working on deeply technical networking problems
Webflow
Best for: Professionals interested in Webflow
Ratings
TailscaleWebflow
4.4
3.7
Overall
4.5
4.0
Work-Life Balance
4.5
3.8
Culture & Values
4.4
3.7
Comp & Benefits
4.2
3.5
Senior Mgmt
4.2
3.5
Career Opps
👍 88% Recommend
👤 92% CEO Approval (Avery Pennarun)
👍 74% Recommend
👤 78% CEO Approval (CEO)
Culture Values
Tailscale only
💎 Strong Comp & Equity🌈 Diverse & Inclusive🪟 Transparent
Webflow only
🎯 Direct Product Impact🌱 Learning & Growth
Shared
🌐 Remote-Friendly⚖️ Work-Life Balance⚙️ Engineering-Driven
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
Webflow
- Remote-first with genuinely respected work-life balance
- Engineers build a product they're proud of with real user impact
- Leadership changes have shifted culture — communication feels less open
- Onboarding and job security concerns reported by recent hires
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.
Webflow
Webflow — check Glassdoor for detailed reviews.
Open Roles
Tailscale — 52 jobs
💻 Engineering
25
💼 Sales / GTM
11
⚙️ Operations
4
📋 Product
4
📊 Data
2
🎨 Design
2
📣 Marketing
2
Webflow — 60 jobs
💻 Engineering
21
💼 Sales / GTM
19
🎨 Design
5
📣 Marketing
4
👤 HR / People
3
📋 Product
3
🧠 ML / AI
1
Summary
Tailscale scores 4.4/5.0 on Glassdoor with a 4.5 work-life balance rating. Webflow scores 3.7/5.0 overall with a 4.0 WLB. That’s a 0.7-point gap on overall satisfaction.
Both companies share these culture values: Remote-Friendly, Work-Life Balance, Engineering-Driven. Tailscale also emphasizes Strong Comp & Equity, Diverse & Inclusive, Transparent. Webflow also emphasizes Direct Product Impact, Learning & Growth.
On the hiring front, Tailscale has 52 open roles and Webflow has 60 open roles.