Cresta
Mid (~500)
Tailscale
Small (~290)
Best For
Cresta
Best for: Professionals interested in Cresta
Tailscale
Best for: Systems engineers who value location-equal pay, generous parental leave, and working on deeply technical networking problems
Ratings
CrestaTailscale
4.6
4.4
Overall
3.7
4.5
Work-Life Balance
4.7
4.5
Culture & Values
4.6
4.4
Comp & Benefits
4.4
4.2
Senior Mgmt
4.4
4.2
Career Opps
👍 92% Recommend
👤 95% CEO Approval (CEO)
👍 88% Recommend
👤 92% CEO Approval (Avery Pennarun)
Culture Values
Cresta only
🚀 Ship Fast & Iterate🌱 Learning & Growth🎯 Direct Product Impact
Tailscale only
🌐 Remote-Friendly⚖️ Work-Life Balance🌈 Diverse & Inclusive🪟 Transparent
Shared
⚙️ Engineering-Driven💎 Strong Comp & Equity
Pros & Cons
Cresta
- World-class engineering talent with zero politics and deep individual ownership
- Strong comp with real equity upside — median $271k TC for US engineers
- Fast-paced culture can be at odds with work-life balance during sprints
- Hyper-growth means roles and processes are constantly evolving
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
Cresta
Cresta — check Glassdoor for detailed reviews.
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
Cresta — 120 jobs
💻 Engineering
48
💼 Sales / GTM
27
🧠 ML / AI
9
📣 Marketing
8
🎨 Design
6
💰 Finance
3
👤 HR / People
3
⚙️ Operations
3
📋 Product
3
📊 Data
1
Tailscale — 52 jobs
💻 Engineering
25
💼 Sales / GTM
11
⚙️ Operations
4
📋 Product
4
📊 Data
2
🎨 Design
2
📣 Marketing
2
Summary
Cresta scores 4.6/5.0 on Glassdoor with a 3.7 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, Strong Comp & Equity. Cresta also emphasizes Ship Fast & Iterate, Learning & Growth, Direct Product Impact. Tailscale also emphasizes Remote-Friendly, Work-Life Balance, Diverse & Inclusive, Transparent.
On the hiring front, Cresta has 120 open roles and Tailscale has 52 open roles.