Chainguard
Mid (~350)
Tailscale
Small (~290)
Best For
Chainguard
Best for: Security-minded engineers who want remote-first open-source work with strong comp
Tailscale
Best for: Systems engineers who value location-equal pay, generous parental leave, and working on deeply technical networking problems
Ratings
ChainguardTailscale
4.5
4.4
Overall
4.2
4.5
Work-Life Balance
4.3
4.5
Culture & Values
4.2
4.4
Comp & Benefits
4.1
4.2
Senior Mgmt
4.0
4.2
Career Opps
👍 88% Recommend
👤 90% CEO Approval (Dan Lorenc)
👍 88% Recommend
👤 92% CEO Approval (Avery Pennarun)
Culture Values
Chainguard only
🔓 Open Source
Tailscale only
🌈 Diverse & Inclusive🪟 Transparent
Shared
🌐 Remote-Friendly⚙️ Engineering-Driven💎 Strong Comp & Equity⚖️ Work-Life Balance
Pros & Cons
Chainguard
- Fully remote with outstanding benefits — 100% employer-paid insurance for employees and families
- Founders are practitioners who understand what engineers and security teams need
- Growing so fast that some inefficiencies exist, though improving
- Fully remote means you miss in-person interactions with teammates
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
Chainguard
Choose Chainguard if you want to build supply chain security tools in a remote, open-source-first culture with strong equity — but expect a fast-moving startup pace.
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
Chainguard — 63 jobs
💼 Sales / GTM
27
💻 Engineering
24
📣 Marketing
3
📋 Product
2
🎨 Design
1
Tailscale — 52 jobs
💻 Engineering
25
💼 Sales / GTM
11
⚙️ Operations
4
📋 Product
4
📊 Data
2
🎨 Design
2
📣 Marketing
2
Summary
Chainguard scores 4.5/5.0 on Glassdoor with a 4.2 work-life balance rating. Tailscale scores 4.4/5.0 overall with a 4.5 WLB. That’s a 0.1-point gap on overall satisfaction.
Both companies share these culture values: Remote-Friendly, Engineering-Driven, Strong Comp & Equity, Work-Life Balance. Chainguard also emphasizes Open Source. Tailscale also emphasizes Diverse & Inclusive, Transparent.
On the hiring front, Chainguard has 63 open roles and Tailscale has 52 open roles.