GitLab
Large (~2,500)
Tailscale
Small (~290)
Best For
GitLab
Best for: Engineers who want a fully remote, async-first culture with radical transparency
Tailscale
Best for: Systems engineers who value location-equal pay, generous parental leave, and working on deeply technical networking problems
Ratings
GitLabTailscale
3.9
4.4
Overall
3.9
4.5
Work-Life Balance
4.0
4.5
Culture & Values
3.8
4.4
Comp & Benefits
3.5
4.2
Senior Mgmt
3.7
4.2
Career Opps
👍 75% Recommend
👤 70% CEO Approval (Sid Sijbrandij)
👍 88% Recommend
👤 92% CEO Approval (Avery Pennarun)
Culture Values
GitLab only
📡 Async-First🔓 Open Source
Tailscale only
💎 Strong Comp & Equity⚙️ Engineering-Driven🌈 Diverse & Inclusive
Shared
🌐 Remote-Friendly🪟 Transparent⚖️ Work-Life Balance
Pros & Cons
GitLab
- Best-in-class all-remote culture — truly async-first with genuine flexibility
- Radically transparent company with a public handbook and open processes
- Revenue organization has seen quota chaos and low morale
- Some leadership instability at the C-suite level
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
GitLab
Choose GitLab if you want the gold standard of all-remote work with public handbook and async processes — but expect bureaucracy at scale and comp below top-tier.
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
GitLab — 195 jobs
💻 Engineering
79
💼 Sales / GTM
67
📋 Product
10
⚖️ Legal
5
📊 Data
4
🎨 Design
4
📣 Marketing
4
👤 HR / People
2
⚙️ Operations
2
Tailscale — 52 jobs
💻 Engineering
25
💼 Sales / GTM
11
⚙️ Operations
4
📋 Product
4
📊 Data
2
🎨 Design
2
📣 Marketing
2
Summary
GitLab scores 3.9/5.0 on Glassdoor with a 3.9 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: Remote-Friendly, Transparent, Work-Life Balance. GitLab also emphasizes Async-First, Open Source. Tailscale also emphasizes Strong Comp & Equity, Engineering-Driven, Diverse & Inclusive.
On the hiring front, GitLab has 195 open roles and Tailscale has 52 open roles.