Poolside
Small (~150)
Tailscale
Small (~290)
Best For
Poolside
Best for: AI researchers who want frontier code generation work with genuine remote flexibility and Paris offsites
Tailscale
Best for: Systems engineers who value location-equal pay, generous parental leave, and working on deeply technical networking problems
Ratings
PoolsideTailscale
3.8
4.4
Overall
3.5
4.5
Work-Life Balance
3.9
4.5
Culture & Values
3.8
4.4
Comp & Benefits
3.6
4.2
Senior Mgmt
3.6
4.2
Career Opps
👍 76% Recommend
👤 80% CEO Approval (Jason Warner)
👍 88% Recommend
👤 92% CEO Approval (Avery Pennarun)
Culture Values
Poolside only
🤝 Flat Hierarchy🧩 Wears Many Hats🌱 Learning & Growth
Tailscale only
⚖️ Work-Life Balance💎 Strong Comp & Equity🌈 Diverse & Inclusive🪟 Transparent
Shared
⚙️ Engineering-Driven🌐 Remote-Friendly
Pros & Cons
Poolside
- Remote-first with monthly Paris gatherings
- Cutting-edge code generation research
- Early-stage with limited structure
- Comp may trail larger AI labs
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
Poolside
Choose Poolside if you want cutting-edge code AI research on a remote-first flat team (ex-GitHub CTO leadership) — but expect early-stage ambiguity and comp that trails the larger AI labs.
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
Poolside — 12 jobs
💻 Engineering
9
📊 Data
2
🧠 ML / AI
1
Tailscale — 52 jobs
💻 Engineering
25
💼 Sales / GTM
11
⚙️ Operations
4
📋 Product
4
📊 Data
2
🎨 Design
2
📣 Marketing
2
Summary
Poolside scores 3.8/5.0 on Glassdoor with a 3.5 work-life balance rating. Tailscale scores 4.4/5.0 overall with a 4.5 WLB. That’s a 0.6-point gap on overall satisfaction.
Both companies share these culture values: Engineering-Driven, Remote-Friendly. Poolside also emphasizes Flat Hierarchy, Wears Many Hats, Learning & Growth. Tailscale also emphasizes Work-Life Balance, Strong Comp & Equity, Diverse & Inclusive, Transparent.
On the hiring front, Poolside has 12 open roles and Tailscale has 52 open roles.