Decagon
Small (~210)
Sierra
Large (~500)
Best For
Decagon
Best for: Builders who want to ship AI customer support agents directly to F500 customers with technical founders deeply involved
Sierra
Best for: Builders who want to work with proven Salesforce and Google leadership on enterprise AI agents
Ratings
DecagonSierra
3.9
4.0
Overall
3.7
3.5
Work-Life Balance
3.8
4.1
Culture & Values
3.2
4.0
Comp & Benefits
3.7
3.8
Senior Mgmt
3.7
3.8
Career Opps
👍 75% Recommend
👤 85% CEO Approval (Jesse Zhang)
👍 80% Recommend
👤 84% CEO Approval (Bret Taylor)
Culture Values
Decagon only
🎯 Direct Product Impact
Sierra only
🌱 Learning & Growth
Shared
⚙️ Engineering-Driven🚀 Ship Fast & Iterate💎 Strong Comp & Equity
Pros & Cons
Decagon
- Strong engineering-driven culture with technical founders still deeply involved
- Ship meaningful AI features to enterprise customers every week
- Intense workload and high expectations — not a typical 40-hour week
- SF-centric; most roles expect in-office presence
Sierra
- Elite founders with proven track records
- Strong equity at $10B valuation
- In-person-first culture
- Competitive intensity may not suit everyone
Bottom Line
Decagon
Choose Decagon if you want intense builder energy at a $4.5B Series D AI agents startup with real enterprise revenue — but expect SF office-centric culture and cash comp that trails top AI labs.
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
Decagon — 95 jobs
💼 Sales / GTM
32
💻 Engineering
25
📋 Product
7
🧠 ML / AI
6
⚙️ Operations
3
⚖️ Legal
2
📣 Marketing
2
📊 Data
1
🎨 Design
1
👤 HR / People
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
Decagon scores 3.9/5.0 on Glassdoor with a 3.7 work-life balance rating. Sierra scores 4.0/5.0 overall with a 3.5 WLB. That’s a 0.1-point gap on overall satisfaction.
Both companies share these culture values: Engineering-Driven, Ship Fast & Iterate, Strong Comp & Equity. Decagon also emphasizes Direct Product Impact. Sierra also emphasizes Learning & Growth.
On the hiring front, Decagon has 95 open roles and Sierra has 134 open roles.