Glean
Large (~1,475)
Tailscale
Small (~290)
Best For
Glean
Best for: AI engineers who want to work on enterprise search with ex-Google leadership and don't mind below-market base pay offset by strong equity upside
Tailscale
Best for: Systems engineers who value location-equal pay, generous parental leave, and working on deeply technical networking problems
Ratings
GleanTailscale
4.2
4.4
Overall
3.8
4.5
Work-Life Balance
4.3
4.5
Culture & Values
4.2
4.4
Comp & Benefits
4.0
4.2
Senior Mgmt
4.0
4.2
Career Opps
👍 84% Recommend
👤 88% CEO Approval (Arvind Jain)
👍 88% Recommend
👤 92% CEO Approval (Avery Pennarun)
Culture Values
Glean only
🌱 Learning & Growth🎯 Direct Product Impact🚀 Ship Fast & Iterate
Tailscale only
🌐 Remote-Friendly⚖️ Work-Life Balance💎 Strong Comp & Equity🌈 Diverse & Inclusive
Shared
⚙️ Engineering-Driven🪟 Transparent
Pros & Cons
Glean
- World-class AI talent — learn from ex-Google leadership on cutting-edge enterprise search
- Transparent collaborative culture with strong career growth
- Below-market compensation — comp rated only 3.6/5
- Sales org has high churn and toxicity problems in EMEA and US
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
Glean
Top-tier AI engineering talent and explosive growth, but comp lags peers and the sales org has churn problems — the engineering side is the real draw.
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
Glean — 196 jobs
💼 Sales / GTM
68
💻 Engineering
42
📋 Product
16
📣 Marketing
10
👤 HR / People
8
🧠 ML / AI
6
🎨 Design
5
📊 Data
3
⚙️ Operations
3
Tailscale — 44 jobs
💻 Engineering
25
📋 Product
6
💼 Sales / GTM
5
📊 Data
2
📣 Marketing
2
⚙️ Operations
2
Summary
Glean 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, Transparent. Glean also emphasizes Learning & Growth, Direct Product Impact, Ship Fast & Iterate. Tailscale also emphasizes Remote-Friendly, Work-Life Balance, Strong Comp & Equity, Diverse & Inclusive.
On the hiring front, Glean has 196 open roles and Tailscale has 44 open roles.