PostHog
Small (~170)
Tailscale
Small (~290)
Best For
PostHog
Best for: Self-directed engineers who want radical transparency, no meetings, and full ownership of their product area
Tailscale
Best for: Systems engineers who value location-equal pay, generous parental leave, and working on deeply technical networking problems
Ratings
PostHogTailscale
4.3
4.4
Overall
4.5
4.5
Work-Life Balance
4.4
4.5
Culture & Values
4.3
4.4
Comp & Benefits
4.1
4.2
Senior Mgmt
4.1
4.2
Career Opps
👍 86% Recommend
👤 90% CEO Approval (James Hawkins)
👍 88% Recommend
👤 92% CEO Approval (Avery Pennarun)
Culture Values
PostHog only
🔓 Open Source📡 Async-First🤝 Flat Hierarchy🧩 Wears Many Hats
Tailscale only
⚖️ Work-Life Balance💎 Strong Comp & Equity⚙️ Engineering-Driven🌈 Diverse & Inclusive
Shared
🪟 Transparent🌐 Remote-Friendly
Pros & Cons
PostHog
- Extreme transparency — public handbook, open-source everything, radical autonomy
- Generous compensation with competitive pay, equity, and home office budget
- Small team means limited career progression paths
- Top-down decision-making can sometimes override team input
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
PostHog
Radically transparent open-source culture with 2-3 person autonomous teams, no deadlines, and a public handbook — ideal if you're self-motivated, tough if you need structure.
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
PostHog — 14 jobs
💻 Engineering
6
💼 Sales / GTM
3
📋 Product
1
Tailscale — 52 jobs
💻 Engineering
25
💼 Sales / GTM
11
⚙️ Operations
4
📋 Product
4
📊 Data
2
🎨 Design
2
📣 Marketing
2
Summary
PostHog scores 4.3/5.0 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 0.1-point gap on overall satisfaction.
Both companies share these culture values: Transparent, Remote-Friendly. PostHog also emphasizes Open Source, Async-First, Flat Hierarchy, Wears Many Hats. Tailscale also emphasizes Work-Life Balance, Strong Comp & Equity, Engineering-Driven, Diverse & Inclusive.
On the hiring front, PostHog has 14 open roles and Tailscale has 52 open roles.