Datadog
Large (~6,000)
HubSpot
Large (~8,000)
Best For
Datadog
Best for: Engineers who want strong comp and interesting scale challenges in cloud observability
HubSpot
Best for: People who prioritize genuine work-life balance and a transparent, inclusive culture
Ratings
DatadogHubSpot
4.2
4.3
Overall
3.8
4.1
Work-Life Balance
4.3
4.5
Culture & Values
4.4
3.9
Comp & Benefits
3.8
4.1
Senior Mgmt
4.0
4.0
Career Opps
👍 80% Recommend
👤 87% CEO Approval (Olivier Pomel)
👍 87% Recommend
👤 92% CEO Approval (Yamini Rangan)
Culture Values
Datadog only
⚙️ Engineering-Driven🚀 Ship Fast & Iterate🎯 Direct Product Impact💎 Strong Comp & Equity
HubSpot only
🌈 Diverse & Inclusive⚖️ Work-Life Balance🪟 Transparent🕐 Flexible Hours🛡️ Safe to Fail
Shared
🌱 Learning & Growth
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
HubSpot
- Culture Code is legendary — transparency, autonomy, flexibility are real
- Remote-first done right with genuine work-life balance
- Enterprise sales culture can clash with engineering
- Comp below FAANG for senior roles
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.
HubSpot
Choose HubSpot if you want legendary culture with real flexibility and psychological safety — but comp is below FAANG.
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
HubSpot — 283 jobs
💼 Sales / GTM
139
💻 Engineering
52
🎨 Design
17
📋 Product
16
📊 Data
7
🎧 Support
7
📣 Marketing
3
🧠 ML / AI
3
👤 HR / People
1
⚖️ Legal
1
⚙️ Operations
1
Summary
Datadog scores 4.2/5.0 on Glassdoor with a 3.8 work-life balance rating. HubSpot scores 4.3/5.0 overall with a 4.1 WLB. That’s a 0.1-point gap on overall satisfaction.
Both companies share these culture values: Learning & Growth. Datadog also emphasizes Engineering-Driven, Ship Fast & Iterate, Direct Product Impact, Strong Comp & Equity. HubSpot also emphasizes Diverse & Inclusive, Work-Life Balance, Transparent, Flexible Hours, Safe to Fail.
On the hiring front, Datadog has 451 open roles and HubSpot has 283 open roles.