HubSpot
Large (~8,000)
Tailscale
Small (~290)
Best For
HubSpot
Best for: People who prioritize genuine work-life balance and a transparent, inclusive culture
Tailscale
Best for: Professionals interested in Tailscale
Ratings
HubSpotTailscale
4.3
4.4
Overall
4.1
4.5
Work-Life Balance
4.5
4.5
Culture & Values
3.9
4.4
Comp & Benefits
4.1
4.2
Senior Mgmt
4.0
4.2
Career Opps
👍 87% Recommend
👤 92% CEO Approval (Yamini Rangan)
👍 88% Recommend
👤 92% CEO Approval (CEO)
Culture Values
HubSpot only
🌱 Learning & Growth🕐 Flexible Hours🛡️ Safe to Fail
Tailscale only
🌐 Remote-Friendly💎 Strong Comp & Equity⚙️ Engineering-Driven
Shared
🌈 Diverse & Inclusive⚖️ Work-Life Balance🪟 Transparent
Pros & Cons
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
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
HubSpot
Choose HubSpot if you want legendary culture with real flexibility and psychological safety — but comp is below FAANG.
Tailscale
Tailscale — check Glassdoor for detailed reviews.
Open Roles
HubSpot — 265 jobs
💼 Sales / GTM
133
💻 Engineering
51
🎨 Design
15
📋 Product
13
📊 Data
7
🎧 Support
7
📣 Marketing
6
👤 HR / People
3
🧠 ML / AI
3
⚙️ Operations
2
⚖️ Legal
1
Tailscale — 36 jobs
💻 Engineering
25
📋 Product
4
📊 Data
2
📣 Marketing
2
💼 Sales / GTM
1