Tailscale
Small (~290)
Twilio
Large (~5,500)
Best For
Tailscale
Best for: Systems engineers who value location-equal pay, generous parental leave, and working on deeply technical networking problems
Twilio
Best for: Professionals interested in Twilio
Ratings
TailscaleTwilio
4.4
3.9
Overall
4.5
4.1
Work-Life Balance
4.5
4.0
Culture & Values
4.4
3.9
Comp & Benefits
4.2
3.7
Senior Mgmt
4.2
3.7
Career Opps
👍 88% Recommend
👤 92% CEO Approval (Avery Pennarun)
👍 78% Recommend
👤 82% CEO Approval (CEO)
Culture Values
Tailscale only
🌈 Diverse & Inclusive🪟 Transparent
Twilio only
🔓 Open Source🌱 Learning & Growth
Shared
🌐 Remote-Friendly⚖️ Work-Life Balance💎 Strong Comp & Equity⚙️ Engineering-Driven
Pros & Cons
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
Twilio
- Genuine remote-first flexibility with excellent work-life balance
- Strong compensation, benefits, and engineering-driven culture
- Frequent reorgs and leadership changes create uncertainty
- Culture has shifted from creative builders to more corporate, profit-driven focus
Bottom Line
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.
Twilio
Twilio — check Glassdoor for detailed reviews.
Open Roles
Tailscale — 52 jobs
💻 Engineering
25
💼 Sales / GTM
11
⚙️ Operations
4
📋 Product
4
📊 Data
2
🎨 Design
2
📣 Marketing
2
Twilio — 143 jobs
💼 Sales / GTM
44
💻 Engineering
43
📋 Product
8
🧠 ML / AI
7
📣 Marketing
6
⚙️ Operations
3
📊 Data
2
🎨 Design
2
💰 Finance
2
👤 HR / People
2
⚖️ Legal
2
Summary
Tailscale scores 4.4/5.0 on Glassdoor with a 4.5 work-life balance rating. Twilio scores 3.9/5.0 overall with a 4.1 WLB. That’s a 0.5-point gap on overall satisfaction.
Both companies share these culture values: Remote-Friendly, Work-Life Balance, Strong Comp & Equity, Engineering-Driven. Tailscale also emphasizes Diverse & Inclusive, Transparent. Twilio also emphasizes Open Source, Learning & Growth.
On the hiring front, Tailscale has 52 open roles and Twilio has 143 open roles.