Brex
Large (~1,600)
Tailscale
Small (~290)
Best For
Brex
Best for: Engineers who want to build AI-powered fintech at massive scale with smart colleagues
Tailscale
Best for: Systems engineers who value location-equal pay, generous parental leave, and working on deeply technical networking problems
Ratings
BrexTailscale
4.0
4.4
Overall
3.9
4.5
Work-Life Balance
3.8
4.5
Culture & Values
4.0
4.4
Comp & Benefits
3.5
4.2
Senior Mgmt
3.6
4.2
Career Opps
👍 77% Recommend
👤 71% CEO Approval (Pedro Franceschi)
👍 88% Recommend
👤 92% CEO Approval (Avery Pennarun)
Culture Values
Brex only
🚀 Ship Fast & Iterate🎯 Direct Product Impact🌱 Learning & Growth
Tailscale only
🌐 Remote-Friendly⚖️ Work-Life Balance💎 Strong Comp & Equity🌈 Diverse & Inclusive
Shared
⚙️ Engineering-Driven🪟 Transparent
Pros & Cons
Brex
- Innovation-driven culture with incredibly smart, passionate, and supportive colleagues
- Strong benefits and time off actively encouraged with flexible scheduling
- Culture of overworking — many departments understaffed relative to workload expectations
- Multiple rounds of layoffs in recent years have created uncertainty and morale challenges
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
Brex
Choose Brex if you want to build AI-powered fintech at massive scale with smart colleagues — but expect intense workloads and some organizational instability from recent layoffs.
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
Brex — 235 jobs
💼 Sales / GTM
72
💻 Engineering
49
📋 Product
18
🎨 Design
15
📣 Marketing
14
👤 HR / People
13
📊 Data
10
⚖️ Legal
6
💰 Finance
3
⚙️ Operations
3
🎧 Support
2
Tailscale — 52 jobs
💻 Engineering
25
💼 Sales / GTM
11
⚙️ Operations
4
📋 Product
4
📊 Data
2
🎨 Design
2
📣 Marketing
2
Summary
Brex scores 4.0/5.0 on Glassdoor with a 3.9 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, Transparent. Brex also emphasizes Ship Fast & Iterate, Direct Product Impact, Learning & Growth. Tailscale also emphasizes Remote-Friendly, Work-Life Balance, Strong Comp & Equity, Diverse & Inclusive.
On the hiring front, Brex has 235 open roles and Tailscale has 52 open roles.