Stripe
Large (~8,000)
Tailscale
Small (~290)
Best For
Stripe
Best for: Engineers who value code quality, writing culture, and fintech at the highest level
Tailscale
Best for: Professionals interested in Tailscale
Ratings
StripeTailscale
4.0
4.4
Overall
3.6
4.5
Work-Life Balance
4.1
4.5
Culture & Values
4.5
4.4
Comp & Benefits
3.7
4.2
Senior Mgmt
3.8
4.2
Career Opps
👍 80% Recommend
👤 82% CEO Approval (Patrick Collison)
👍 88% Recommend
👤 92% CEO Approval (CEO)
Culture Values
Stripe only
🌱 Learning & Growth🎯 Direct Product Impact
Tailscale only
🌐 Remote-Friendly⚖️ Work-Life Balance🌈 Diverse & Inclusive
Shared
⚙️ Engineering-Driven💎 Strong Comp & Equity🪟 Transparent
Pros & Cons
Stripe
- Engineering culture is elite — code quality and writing culture are best-in-class
- Top compensation in fintech — competitive base, equity, and benefits
- Perfectionism can slow shipping — high bar sometimes means slower velocity
- The 2022-23 layoffs affected morale — company has been rebuilding confidence
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
Stripe
Choose Stripe if you want elite engineering culture with top comp — but perfectionism can slow shipping velocity.
Tailscale
Tailscale — check Glassdoor for detailed reviews.
Open Roles
Stripe — 526 jobs
💼 Sales / GTM
112
💻 Engineering
108
📋 Product
56
⚙️ Operations
38
📣 Marketing
34
💰 Finance
21
📊 Data
20
👤 HR / People
19
⚖️ Legal
14
🎨 Design
13
🧠 ML / AI
12
🎧 Support
3
Tailscale — 36 jobs
💻 Engineering
25
📋 Product
4
📊 Data
2
📣 Marketing
2
💼 Sales / GTM
1