Datadog
Large (~6,000)
Twilio
Large (~5,500)
Best For
Datadog
Best for: Engineers who want strong comp and interesting scale challenges in cloud observability
Twilio
Best for: Professionals interested in Twilio
Ratings
DatadogTwilio
4.2
3.9
Overall
3.8
4.1
Work-Life Balance
4.3
4.0
Culture & Values
4.4
3.9
Comp & Benefits
3.8
3.7
Senior Mgmt
4.0
3.7
Career Opps
👍 80% Recommend
👤 87% CEO Approval (Olivier Pomel)
👍 78% Recommend
👤 82% CEO Approval (CEO)
Culture Values
Datadog only
🚀 Ship Fast & Iterate🎯 Direct Product Impact
Twilio only
🌐 Remote-Friendly⚖️ Work-Life Balance🔓 Open Source
Shared
⚙️ Engineering-Driven🌱 Learning & Growth💎 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
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
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.
Twilio
Twilio — check Glassdoor for detailed reviews.
Open Roles
Datadog — 422 jobs
💼 Sales / GTM
218
💻 Engineering
83
📋 Product
28
📣 Marketing
12
👤 HR / People
8
🧠 ML / AI
8
🎨 Design
6
⚖️ Legal
3
⚙️ Operations
3
📊 Data
2
💰 Finance
1
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
Datadog scores 4.2/5.0 on Glassdoor with a 3.8 work-life balance rating. Twilio scores 3.9/5.0 overall with a 4.1 WLB. That’s a 0.3-point gap on overall satisfaction.
Both companies share these culture values: Engineering-Driven, Learning & Growth, Strong Comp & Equity. Datadog also emphasizes Ship Fast & Iterate, Direct Product Impact. Twilio also emphasizes Remote-Friendly, Work-Life Balance, Open Source.
On the hiring front, Datadog has 422 open roles and Twilio has 143 open roles.