Perplexity AI
Mid (~500)
Tailscale
Small (~290)
Best For
Perplexity AI
Best for: Builders who thrive on speed and want massive user-facing impact at a rocketship
Tailscale
Best for: Professionals interested in Tailscale
Ratings
Perplexity AITailscale
4.7
4.4
Overall
3.3
4.5
Work-Life Balance
4.8
4.5
Culture & Values
4.5
4.4
Comp & Benefits
4.5
4.2
Senior Mgmt
4.2
4.2
Career Opps
👍 92% Recommend
👤 95% CEO Approval (Aravind Srinivas)
👍 88% Recommend
👤 92% CEO Approval (CEO)
Culture Values
Perplexity AI 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
Perplexity AI
- Fastest-growing AI product — real users, real revenue, genuine product-market fit
- Small team, massive impact per engineer — your work ships to millions quickly
- Startup intensity — expect long hours and high expectations
- Growing pains as the team scales — roles and responsibilities shift frequently
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
Perplexity AI
Choose Perplexity if you want the fastest-growing AI product and huge per-engineer impact — but expect startup intensity.
Tailscale
Tailscale — check Glassdoor for detailed reviews.
Open Roles
Perplexity AI — 81 jobs
💻 Engineering
44
🧠 ML / AI
7
📊 Data
5
⚖️ Legal
5
💼 Sales / GTM
4
📣 Marketing
3
💰 Finance
1
👤 HR / People
1
⚙️ Operations
1
📋 Product
1
🎧 Support
1
Tailscale — 36 jobs
💻 Engineering
25
📋 Product
4
📊 Data
2
📣 Marketing
2
💼 Sales / GTM
1