Chainguard
Mid (~350)
Sierra
Large (~500)
Best For
Chainguard
Best for: Security-minded engineers who want remote-first open-source work with strong comp
Sierra
Best for: Builders who want to work with proven Salesforce and Google leadership on enterprise AI agents
Ratings
ChainguardSierra
4.5
4.0
Overall
4.2
3.5
Work-Life Balance
4.3
4.1
Culture & Values
4.2
4.0
Comp & Benefits
4.1
3.8
Senior Mgmt
4.0
3.8
Career Opps
👍 88% Recommend
👤 90% CEO Approval (Dan Lorenc)
👍 80% Recommend
👤 84% CEO Approval (Bret Taylor)
Culture Values
Chainguard only
🌐 Remote-Friendly🔓 Open Source⚖️ Work-Life Balance
Sierra only
🚀 Ship Fast & Iterate🌱 Learning & Growth
Shared
⚙️ Engineering-Driven💎 Strong Comp & Equity
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
Sierra
- Elite founders with proven track records
- Strong equity at $10B valuation
- In-person-first culture
- Competitive intensity may not suit everyone
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.
Sierra
Choose Sierra if you want elite founders (Bret Taylor, Clay Bavor) and strong equity at a $10B enterprise AI company — but it's in-person-first and the competitive intensity won't suit everyone.
Open Roles
Chainguard — 63 jobs
💼 Sales / GTM
27
💻 Engineering
24
📣 Marketing
3
📋 Product
2
🎨 Design
1
Sierra — 134 jobs
💻 Engineering
42
💼 Sales / GTM
27
📋 Product
15
👤 HR / People
7
🎨 Design
5
⚖️ Legal
5
📣 Marketing
5
⚙️ Operations
5
📊 Data
2
💰 Finance
1
Summary
Chainguard scores 4.5/5.0 on Glassdoor with a 4.2 work-life balance rating. Sierra scores 4.0/5.0 overall with a 3.5 WLB. That’s a 0.5-point gap on overall satisfaction.
Both companies share these culture values: Engineering-Driven, Strong Comp & Equity. Chainguard also emphasizes Remote-Friendly, Open Source, Work-Life Balance. Sierra also emphasizes Ship Fast & Iterate, Learning & Growth.
On the hiring front, Chainguard has 63 open roles and Sierra has 134 open roles.