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: Systems engineers who value location-equal pay, generous parental leave, and working on deeply technical networking problems
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 (Avery Pennarun)
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
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
Ramp — 128 jobs
💻 Engineering
32
💼 Sales / GTM
25
⚙️ Operations
7
💰 Finance
6
📋 Product
6
📣 Marketing
5
📊 Data
3
🎨 Design
2
⚖️ Legal
2
👤 HR / People
1
Tailscale — 52 jobs
💻 Engineering
25
💼 Sales / GTM
11
⚙️ Operations
4
📋 Product
4
📊 Data
2
🎨 Design
2
📣 Marketing
2
Summary
Ramp scores 4.2/5.0 on Glassdoor with a 3.5 work-life balance rating. Tailscale scores 4.4/5.0 overall with a 4.5 WLB. That’s a 0.2-point gap on overall satisfaction.
Both companies share these culture values: Engineering-Driven, Transparent, Strong Comp & Equity. Ramp also emphasizes Ship Fast & Iterate, Direct Product Impact, Learning & Growth. Tailscale also emphasizes Remote-Friendly, Work-Life Balance, Diverse & Inclusive.
On the hiring front, Ramp has 128 open roles and Tailscale has 52 open roles.