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: Professionals interested in Tailscale
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 (CEO)
Culture Values
Brex only
🚀 Ship Fast & Iterate🎯 Direct Product Impact🌱 Learning & Growth
Tailscale only
⚖️ Work-Life Balance💎 Strong Comp & Equity🌈 Diverse & Inclusive
Shared
⚙️ Engineering-Driven🪟 Transparent🌐 Remote-Friendly
Pros & Cons
Brex
- Innovation-driven culture with incredibly smart, passionate, and supportive colleagues
- Remote-first with strong benefits — 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
Tailscale — check Glassdoor for detailed reviews.
Open Roles
Brex — 253 jobs
💼 Sales / GTM
78
💻 Engineering
53
📋 Product
20
👤 HR / People
16
🎨 Design
15
📣 Marketing
15
📊 Data
10
💰 Finance
10
⚖️ Legal
6
⚙️ Operations
5
Tailscale — 39 jobs
💻 Engineering
25
📋 Product
4
💼 Sales / GTM
4
📊 Data
2
📣 Marketing
2