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: Systems engineers who value location-equal pay, generous parental leave, and working on deeply technical networking problems
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 (Avery Pennarun)
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
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
Stripe — 490 jobs
💻 Engineering
118
💼 Sales / GTM
98
📋 Product
44
⚙️ Operations
39
📣 Marketing
34
💰 Finance
22
📊 Data
16
🎨 Design
15
⚖️ Legal
12
🧠 ML / AI
9
👤 HR / People
7
🎧 Support
4
Tailscale — 52 jobs
💻 Engineering
25
💼 Sales / GTM
11
⚙️ Operations
4
📋 Product
4
📊 Data
2
🎨 Design
2
📣 Marketing
2
Summary
Stripe 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, Transparent. Stripe also emphasizes Learning & Growth, Direct Product Impact. Tailscale also emphasizes Remote-Friendly, Work-Life Balance, Diverse & Inclusive.
On the hiring front, Stripe has 490 open roles and Tailscale has 52 open roles.