Chainguard
Mid (~350)
Pylon
Small (~70)
Best For
Chainguard
Best for: Security-minded engineers who want remote-first open-source work with strong comp
Pylon
Best for: Early-career engineers who want YC-style startup intensity and direct product ownership at a small, fast-moving team
Ratings
ChainguardPylon
4.5
3.0
Overall
4.2
3.5
Work-Life Balance
4.3
3.1
Culture & Values
4.2
3.0
Comp & Benefits
4.1
2.8
Senior Mgmt
4.0
2.8
Career Opps
👍 88% Recommend
👤 90% CEO Approval (Dan Lorenc)
👍 60% Recommend
👤 63% CEO Approval (Marty Kausas)
Culture Values
Chainguard only
🌐 Remote-Friendly🔓 Open Source⚙️ Engineering-Driven💎 Strong Comp & Equity⚖️ Work-Life Balance
Pylon only
🚀 Ship Fast & Iterate🧩 Wears Many Hats🎯 Direct Product Impact
Shared
None
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
Pylon
- YC + a16z backed with strong product-market fit in B2B customer support
- Small team with outsized ownership — every engineer directly shapes the product
- Polarized reviews — aggressive culture reported by some employees
- Very early-stage with minimal processes — only 4 Glassdoor reviews
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.
Pylon
Small YC + a16z-backed team with strong product-market fit in B2B support — but polarized Glassdoor reviews flag an aggressive culture and minimal processes.
Open Roles
Chainguard — 63 jobs
💼 Sales / GTM
27
💻 Engineering
24
📣 Marketing
3
📋 Product
2
🎨 Design
1
Pylon — 31 jobs
💼 Sales / GTM
11
💻 Engineering
10
🎨 Design
3
📣 Marketing
2
👤 HR / People
1
📋 Product
1
Summary
Chainguard scores 4.5/5.0 on Glassdoor with a 4.2 work-life balance rating. Pylon scores 3.0/5.0 overall with a 3.5 WLB. That’s a 1.5-point gap on overall satisfaction.
On the hiring front, Chainguard has 63 open roles and Pylon has 31 open roles.