OpenAI
Large (~3,500)
Tailscale
Small (~290)
Best For
OpenAI
Best for: Professionals interested in OpenAI
Tailscale
Best for: Professionals interested in Tailscale
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 (CEO)
👍 88% Recommend
👤 92% CEO Approval (CEO)
Culture Values
OpenAI only
🚀 Ship Fast & Iterate🌱 Learning & Growth🤖 Ethical AI / Safety🎯 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
OpenAI — check Glassdoor for detailed reviews.
Tailscale
Tailscale — check Glassdoor for detailed reviews.
Open Roles
OpenAI — 626 jobs
💻 Engineering
293
💼 Sales / GTM
49
📋 Product
32
🧠 ML / AI
31
📊 Data
27
📣 Marketing
23
⚙️ Operations
17
⚖️ Legal
15
🎨 Design
11
💰 Finance
11
👤 HR / People
8
🎧 Support
4
Tailscale — 36 jobs
💻 Engineering
25
📋 Product
4
📊 Data
2
📣 Marketing
2
💼 Sales / GTM
1