Harvey
Medium (~350)
Tailscale
Small (~290)
Best For
Harvey
Best for: Engineers who want to transform legal work with AI at a well-funded unicorn with exceptional comp
Tailscale
Best for: Systems engineers who value location-equal pay, generous parental leave, and working on deeply technical networking problems
Ratings
HarveyTailscale
3.9
4.4
Overall
3.4
4.5
Work-Life Balance
4.0
4.5
Culture & Values
3.9
4.4
Comp & Benefits
3.7
4.2
Senior Mgmt
3.7
4.2
Career Opps
👍 78% Recommend
👤 82% CEO Approval (Winston Weinberg)
👍 88% Recommend
👤 92% CEO Approval (Avery Pennarun)
Culture Values
Harvey only
🚀 Ship Fast & Iterate🌱 Learning & Growth🎯 Direct Product Impact
Tailscale only
🌐 Remote-Friendly⚖️ Work-Life Balance🌈 Diverse & Inclusive🪟 Transparent
Shared
⚙️ Engineering-Driven💎 Strong Comp & Equity
Pros & Cons
Harvey
- Exceptional comp and equity packages
- Smart, driven colleagues who support each other
- Intense pace with long hours
- Growing pains and internal politics
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
Harvey
Choose Harvey if you want exceptional equity, smart colleagues, and the chance to reshape the legal industry with AI — but expect relentless pace, long hours, and growing-company politics.
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
Harvey — 230 jobs
💻 Engineering
79
💼 Sales / GTM
47
⚙️ Operations
21
📋 Product
18
⚖️ Legal
17
📣 Marketing
13
🎨 Design
10
👤 HR / People
9
📊 Data
2
Tailscale — 52 jobs
💻 Engineering
25
💼 Sales / GTM
11
⚙️ Operations
4
📋 Product
4
📊 Data
2
🎨 Design
2
📣 Marketing
2
Summary
Harvey scores 3.9/5.0 on Glassdoor with a 3.4 work-life balance rating. Tailscale scores 4.4/5.0 overall with a 4.5 WLB. That’s a 0.5-point gap on overall satisfaction.
Both companies share these culture values: Engineering-Driven, Strong Comp & Equity. Harvey also emphasizes Ship Fast & Iterate, Learning & Growth, Direct Product Impact. Tailscale also emphasizes Remote-Friendly, Work-Life Balance, Diverse & Inclusive, Transparent.
On the hiring front, Harvey has 230 open roles and Tailscale has 52 open roles.