Granola
Small (~50)
Tailscale
Small (~290)
Best For
Granola
Best for: Craft-focused generalists who love native macOS development and want to build a consumer-quality AI product people genuinely love
Tailscale
Best for: Systems engineers who value location-equal pay, generous parental leave, and working on deeply technical networking problems
Ratings
GranolaTailscale
4.8
4.4
Overall
4.5
4.5
Work-Life Balance
5.0
4.5
Culture & Values
4.5
4.4
Comp & Benefits
5.0
4.2
Senior Mgmt
4.7
4.2
Career Opps
👍 100% Recommend
👤 100% CEO Approval (Sam Stephenson)
👍 88% Recommend
👤 92% CEO Approval (Avery Pennarun)
Culture Values
Granola only
🚀 Ship Fast & Iterate🎯 Direct Product Impact🧩 Wears Many Hats
Tailscale only
🌐 Remote-Friendly⚖️ Work-Life Balance🌈 Diverse & Inclusive🪟 Transparent
Shared
⚙️ Engineering-Driven💎 Strong Comp & Equity
Pros & Cons
Granola
- Users absolutely love the product — everyone at Granola genuinely cares about quality
- Plenty of opportunities to work on things that make a real difference on a small team
- 5 days in office by default (with flexibility for life circumstances)
- Small team, so things can be busy — you'll wear many hats
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
Granola
Choose Granola if you want to work on one of the most loved AI products with a small, London-based, in-office team obsessed with craft — but note the 5-days-in-office policy is explicit and non-negotiable.
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
Granola — 16 jobs
💼 Sales / GTM
6
💻 Engineering
4
📣 Marketing
2
🎨 Design
1
👤 HR / People
1
⚖️ Legal
1
⚙️ Operations
1
Tailscale — 52 jobs
💻 Engineering
25
💼 Sales / GTM
11
⚙️ Operations
4
📋 Product
4
📊 Data
2
🎨 Design
2
📣 Marketing
2
Summary
Granola scores 4.8/5.0 on Glassdoor with a 4.5 work-life balance rating. Tailscale scores 4.4/5.0 overall with a 4.5 WLB. That’s a 0.4-point gap on overall satisfaction.
Both companies share these culture values: Engineering-Driven, Strong Comp & Equity. Granola also emphasizes Ship Fast & Iterate, Direct Product Impact, Wears Many Hats. Tailscale also emphasizes Remote-Friendly, Work-Life Balance, Diverse & Inclusive, Transparent.
On the hiring front, Granola has 16 open roles and Tailscale has 52 open roles.