Ramp
Large (~1,000+)
Tailscale
Small (~290)
Best For
Ramp
Best for: Product-minded engineers who want exceptional comp and benefits at the fastest-growing fintech
Tailscale
Best for: Professionals interested in Tailscale
Ratings
RampTailscale
4.2
4.4
Overall
3.5
4.5
Work-Life Balance
4.3
4.5
Culture & Values
4.5
4.4
Comp & Benefits
3.8
4.2
Senior Mgmt
4.0
4.2
Career Opps
👍 82% Recommend
👤 88% CEO Approval (Eric Glyman)
👍 88% Recommend
👤 92% CEO Approval (CEO)
Culture Values
Ramp only
🚀 Ship Fast & Iterate🎯 Direct Product Impact🌱 Learning & Growth
Tailscale only
🌐 Remote-Friendly⚖️ Work-Life Balance🌈 Diverse & Inclusive
Shared
⚙️ Engineering-Driven🪟 Transparent💎 Strong Comp & Equity
Pros & Cons
Ramp
- Exceptional talent and product-driven culture — software engineers rate 4.7/5 on Glassdoor
- Outstanding compensation and benefits — 16 weeks maternity, IVF coverage, free lunch
- Intense work demands — 60+ hour weeks and 10-12 hour days are common
- Shifting to in-office preference — new hires expected 3+ days/week in NYC, SF, or Miami
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
Ramp
Choose Ramp if you want top-tier comp and a product-driven fintech culture — but expect 60+ hour weeks and in-office expectations.
Tailscale
Tailscale — check Glassdoor for detailed reviews.
Open Roles
Ramp — 130 jobs
💻 Engineering
33
💼 Sales / GTM
26
📣 Marketing
9
📋 Product
7
💰 Finance
6
⚙️ Operations
4
📊 Data
3
🎨 Design
2
👤 HR / People
2
⚖️ Legal
1
Tailscale — 36 jobs
💻 Engineering
25
📋 Product
4
📊 Data
2
📣 Marketing
2
💼 Sales / GTM
1