Asana
Large (~1,700)
Tailscale
Small (~290)
Best For
Asana
Best for: Engineers and PMs who want genuine work-life balance and transparent leadership at a public tech company that practices what it preaches about how work should feel
Tailscale
Best for: Systems engineers who value location-equal pay, generous parental leave, and working on deeply technical networking problems
Ratings
AsanaTailscale
4.1
4.4
Overall
4.2
4.5
Work-Life Balance
4.3
4.5
Culture & Values
4.0
4.4
Comp & Benefits
3.8
4.2
Senior Mgmt
4.0
4.2
Career Opps
👍 78% Recommend
👤 90% CEO Approval (Dustin Moskovitz)
👍 88% Recommend
👤 92% CEO Approval (Avery Pennarun)
Culture Values
Asana only
🌱 Learning & Growth🎯 Direct Product Impact
Tailscale only
🌐 Remote-Friendly💎 Strong Comp & Equity⚙️ Engineering-Driven
Shared
⚖️ Work-Life Balance🪟 Transparent🌈 Diverse & Inclusive
Pros & Cons
Asana
- Exceptional work-life balance and supportive team culture
- Highly transparent leadership with strong D&I commitment
- Senior management accountability concerns and frequent reorgs
- Mandatory hybrid schedule — 3 days in office per week
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
Asana
Choose Asana if you want sustainable pace, strong D&I, and a learning-first engineering culture at a public company — but expect hybrid 3-day in-office and some reorg turbulence.
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
Asana — 129 jobs
💻 Engineering
50
💼 Sales / GTM
22
📋 Product
9
⚙️ Operations
8
🎨 Design
6
📊 Data
5
👤 HR / People
3
📣 Marketing
3
⚖️ Legal
2
💰 Finance
1
🎧 Support
1
Tailscale — 52 jobs
💻 Engineering
25
💼 Sales / GTM
11
⚙️ Operations
4
📋 Product
4
📊 Data
2
🎨 Design
2
📣 Marketing
2
Summary
Asana scores 4.1/5.0 on Glassdoor with a 4.2 work-life balance rating. Tailscale scores 4.4/5.0 overall with a 4.5 WLB. That’s a 0.3-point gap on overall satisfaction.
Both companies share these culture values: Work-Life Balance, Transparent, Diverse & Inclusive. Asana also emphasizes Learning & Growth, Direct Product Impact. Tailscale also emphasizes Remote-Friendly, Strong Comp & Equity, Engineering-Driven.
On the hiring front, Asana has 129 open roles and Tailscale has 52 open roles.