Datadog
Large (~6,000)
Tailscale
Small (~290)
Best For
Datadog
Best for: Engineers who want strong comp and interesting scale challenges in cloud observability
Tailscale
Best for: Professionals interested in Tailscale
Ratings
DatadogTailscale
4.2
4.4
Overall
3.8
4.5
Work-Life Balance
4.3
4.5
Culture & Values
4.4
4.4
Comp & Benefits
3.8
4.2
Senior Mgmt
4.0
4.2
Career Opps
👍 80% Recommend
👤 87% CEO Approval (Olivier Pomel)
👍 88% Recommend
👤 92% CEO Approval (CEO)
Culture Values
Datadog 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
Datadog
- Excellent compensation and equity — stock has been a genuine wealth builder for early employees
- Strong engineering culture with smart coworkers and interesting technical challenges at scale
- Fast pace can lead to long hours and pressure to deliver, work-life balance varies by team
- Rapid growth has led to organizational growing pains and bureaucracy creeping in
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
Datadog
Choose Datadog if you want strong comp, interesting scale challenges in observability, and a fast-paced engineering culture — but expect long hours and growing bureaucracy.
Tailscale
Tailscale — check Glassdoor for detailed reviews.
Open Roles
Datadog — 451 jobs
💼 Sales / GTM
217
💻 Engineering
118
📋 Product
28
📣 Marketing
15
👤 HR / People
8
🧠 ML / AI
8
🎨 Design
7
⚙️ Operations
6
⚖️ Legal
3
📊 Data
1
💰 Finance
1
Tailscale — 44 jobs
💻 Engineering
25
📋 Product
6
💼 Sales / GTM
5
📊 Data
2
📣 Marketing
2
⚙️ Operations
2
Summary
Datadog scores 4.2/5.0 on Glassdoor with a 3.8 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. Datadog 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, Datadog has 451 open roles and Tailscale has 44 open roles.