Elastic
Large (~4,000)
Tailscale
Small (~290)
Best For
Elastic
Best for: Professionals interested in Elastic
Tailscale
Best for: Systems engineers who value location-equal pay, generous parental leave, and working on deeply technical networking problems
Ratings
ElasticTailscale
4.0
4.4
Overall
4.1
4.5
Work-Life Balance
4.1
4.5
Culture & Values
4.0
4.4
Comp & Benefits
3.8
4.2
Senior Mgmt
3.8
4.2
Career Opps
👍 80% Recommend
👤 84% CEO Approval (CEO)
👍 88% Recommend
👤 92% CEO Approval (Avery Pennarun)
Culture Values
Elastic only
🔓 Open Source📡 Async-First
Tailscale only
⚙️ Engineering-Driven🌈 Diverse & Inclusive🪟 Transparent
Shared
🌐 Remote-Friendly⚖️ Work-Life Balance💎 Strong Comp & Equity
Pros & Cons
Elastic
- Fully distributed from day one — genuine remote-first culture across 40+ countries
- Open-source DNA means engineers contribute to community, not just internal products
- Cross-timezone coordination means occasional early/late meetings
- Recent leadership shifts have introduced more process and oversight
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
Elastic
Elastic — 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
Elastic — 198 jobs
💻 Engineering
87
💼 Sales / GTM
67
📣 Marketing
8
📋 Product
7
👤 HR / People
4
🎨 Design
3
🧠 ML / AI
3
📊 Data
2
Tailscale — 52 jobs
💻 Engineering
25
💼 Sales / GTM
11
⚙️ Operations
4
📋 Product
4
📊 Data
2
🎨 Design
2
📣 Marketing
2
Summary
Elastic scores 4.0/5.0 on Glassdoor with a 4.1 work-life balance rating. Tailscale scores 4.4/5.0 overall with a 4.5 WLB. That’s a 0.4-point gap on overall satisfaction.
Both companies share these culture values: Remote-Friendly, Work-Life Balance, Strong Comp & Equity. Elastic also emphasizes Open Source, Async-First. Tailscale also emphasizes Engineering-Driven, Diverse & Inclusive, Transparent.
On the hiring front, Elastic has 198 open roles and Tailscale has 52 open roles.