Chainguard
Mid (~350)
Poolside
Small (~150)
Best For
Chainguard
Best for: Security-minded engineers who want remote-first open-source work with strong comp
Poolside
Best for: AI researchers who want frontier code generation work with genuine remote flexibility and Paris offsites
Ratings
ChainguardPoolside
4.5
3.8
Overall
4.2
3.5
Work-Life Balance
4.3
3.9
Culture & Values
4.2
3.8
Comp & Benefits
4.1
3.6
Senior Mgmt
4.0
3.6
Career Opps
👍 88% Recommend
👤 90% CEO Approval (Dan Lorenc)
👍 76% Recommend
👤 80% CEO Approval (Jason Warner)
Culture Values
Chainguard only
🔓 Open Source💎 Strong Comp & Equity⚖️ Work-Life Balance
Poolside only
🤝 Flat Hierarchy🧩 Wears Many Hats🌱 Learning & Growth
Shared
🌐 Remote-Friendly⚙️ Engineering-Driven
Pros & Cons
Chainguard
- Fully remote with outstanding benefits — 100% employer-paid insurance for employees and families
- Founders are practitioners who understand what engineers and security teams need
- Growing so fast that some inefficiencies exist, though improving
- Fully remote means you miss in-person interactions with teammates
Poolside
- Remote-first with monthly Paris gatherings
- Cutting-edge code generation research
- Early-stage with limited structure
- Comp may trail larger AI labs
Bottom Line
Chainguard
Choose Chainguard if you want to build supply chain security tools in a remote, open-source-first culture with strong equity — but expect a fast-moving startup pace.
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.
Open Roles
Chainguard — 63 jobs
💼 Sales / GTM
27
💻 Engineering
24
📣 Marketing
3
📋 Product
2
🎨 Design
1
Poolside — 12 jobs
💻 Engineering
9
📊 Data
2
🧠 ML / AI
1
Summary
Chainguard scores 4.5/5.0 on Glassdoor with a 4.2 work-life balance rating. Poolside scores 3.8/5.0 overall with a 3.5 WLB. That’s a 0.7-point gap on overall satisfaction.
Both companies share these culture values: Remote-Friendly, Engineering-Driven. Chainguard also emphasizes Open Source, Strong Comp & Equity, Work-Life Balance. Poolside also emphasizes Flat Hierarchy, Wears Many Hats, Learning & Growth.
On the hiring front, Chainguard has 63 open roles and Poolside has 12 open roles.