OpenAI
Large (~3,500)
Tailscale
Small (~290)
Best For
OpenAI
Best for: Engineers who want to build frontier AI models at the company defining the industry, with elite compensation
Tailscale
Best for: Systems engineers who value location-equal pay, generous parental leave, and working on deeply technical networking problems
Ratings
OpenAITailscale
4.5
4.4
Overall
3.6
4.5
Work-Life Balance
4.6
4.5
Culture & Values
4.5
4.4
Comp & Benefits
4.3
4.2
Senior Mgmt
4.3
4.2
Career Opps
👍 90% Recommend
👤 95% CEO Approval (Sam Altman)
👍 88% Recommend
👤 92% CEO Approval (Avery Pennarun)
Culture Values
OpenAI only
🚀 Ship Fast & Iterate🌱 Learning & Growth🎯 Direct Product Impact
Tailscale only
🌐 Remote-Friendly⚖️ Work-Life Balance🌈 Diverse & Inclusive🪟 Transparent
Shared
⚙️ Engineering-Driven💎 Strong Comp & Equity
Pros & Cons
OpenAI
- Cutting-edge frontier AI research with world-class colleagues
- Elite compensation — top-tier TC and equity packages
- High-intensity environment — long hours and intense pace are the norm
- Internal politics and rapid org changes as the company scales
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
OpenAI
High-intensity, mission-driven culture with world-class colleagues and top-tier comp — but expect long hours, rapid org changes, and internal politics as the company scales.
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
OpenAI — 655 jobs
💻 Engineering
317
💼 Sales / GTM
57
📋 Product
30
📊 Data
28
🧠 ML / AI
28
📣 Marketing
24
⚙️ Operations
17
⚖️ Legal
13
🎨 Design
10
👤 HR / People
9
💰 Finance
7
🎧 Support
4
Tailscale — 52 jobs
💻 Engineering
25
💼 Sales / GTM
11
⚙️ Operations
4
📋 Product
4
📊 Data
2
🎨 Design
2
📣 Marketing
2
Summary
OpenAI scores 4.5/5.0 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 0.1-point gap on overall satisfaction.
Both companies share these culture values: Engineering-Driven, Strong Comp & Equity. OpenAI also emphasizes Ship Fast & Iterate, Learning & Growth, Direct Product Impact. Tailscale also emphasizes Remote-Friendly, Work-Life Balance, Diverse & Inclusive, Transparent.
On the hiring front, OpenAI has 655 open roles and Tailscale has 52 open roles.