Helsing
Mid (~660)
Tailscale
Small (~290)
Best For
Helsing
Best for: AI/ML engineers motivated by national security and defense who want to apply frontier AI to high-stakes real-world problems in a mission-driven team
Tailscale
Best for: Systems engineers who value location-equal pay, generous parental leave, and working on deeply technical networking problems
Ratings
HelsingTailscale
4.0
4.4
Overall
3.6
4.5
Work-Life Balance
4.1
4.5
Culture & Values
4.0
4.4
Comp & Benefits
3.8
4.2
Senior Mgmt
3.8
4.2
Career Opps
👍 80% Recommend
👤 84% CEO Approval (Gundbert Scherf)
👍 88% Recommend
👤 92% CEO Approval (Avery Pennarun)
Culture Values
Helsing only
🚀 Ship Fast & Iterate🎯 Direct Product Impact🌱 Learning & Growth
Tailscale only
🌐 Remote-Friendly⚖️ Work-Life Balance🌈 Diverse & Inclusive🪟 Transparent
Shared
⚙️ Engineering-Driven💎 Strong Comp & Equity
Pros & Cons
Helsing
- Highest talent density of any tech company — world-class AI and engineering leadership
- Extremely important mission with rewarding impact and competitive salary
- Ridiculous expectations of work hours — high salaries do not mean constant overtime
- Some management not experienced enough to lead; lacking in performance feedback
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
Helsing
Strong engineering culture with a clear mission — but that mission (AI for defense) is not for everyone. Research the ethics carefully before applying; those aligned will find unusually meaningful work.
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
Helsing — 103 jobs
💻 Engineering
51
🧠 ML / AI
8
⚙️ Operations
4
📋 Product
4
💰 Finance
3
🎨 Design
2
📣 Marketing
2
👤 HR / People
1
💼 Sales / GTM
1
🎧 Support
1
Tailscale — 53 jobs
💻 Engineering
25
💼 Sales / GTM
12
📋 Product
6
⚙️ Operations
4
📊 Data
2
📣 Marketing
2
Summary
Helsing scores 4.0/5.0 on Glassdoor with a 3.6 work-life balance rating. Tailscale scores 4.4/5.0 overall with a 4.5 WLB. That’s a 0.4-point gap on overall satisfaction.
Both companies share these culture values: Engineering-Driven, Strong Comp & Equity. Helsing also emphasizes Ship Fast & Iterate, Direct Product Impact, Learning & Growth. Tailscale also emphasizes Remote-Friendly, Work-Life Balance, Diverse & Inclusive, Transparent.
On the hiring front, Helsing has 103 open roles and Tailscale has 53 open roles.