Decagon
Small (~210)
Stripe
Large (~8,000)
Best For
Decagon
Best for: Builders who want to ship AI customer support agents directly to F500 customers with technical founders deeply involved
Stripe
Best for: Engineers who value code quality, writing culture, and fintech at the highest level
Ratings
DecagonStripe
3.9
4.0
Overall
3.7
3.6
Work-Life Balance
3.8
4.1
Culture & Values
3.2
4.5
Comp & Benefits
3.7
3.7
Senior Mgmt
3.7
3.8
Career Opps
👍 75% Recommend
👤 85% CEO Approval (Jesse Zhang)
👍 80% Recommend
👤 82% CEO Approval (Patrick Collison)
Culture Values
Decagon only
🚀 Ship Fast & Iterate
Stripe only
🌱 Learning & Growth🪟 Transparent
Shared
⚙️ Engineering-Driven💎 Strong Comp & Equity🎯 Direct Product Impact
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
Stripe
- Engineering culture is elite — code quality and writing culture are best-in-class
- Top compensation in fintech — competitive base, equity, and benefits
- Perfectionism can slow shipping — high bar sometimes means slower velocity
- The 2022-23 layoffs affected morale — company has been rebuilding confidence
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.
Stripe
Choose Stripe if you want elite engineering culture with top comp — but perfectionism can slow shipping velocity.
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
Stripe — 490 jobs
💻 Engineering
118
💼 Sales / GTM
98
📋 Product
44
⚙️ Operations
39
📣 Marketing
34
💰 Finance
22
📊 Data
16
🎨 Design
15
⚖️ Legal
12
🧠 ML / AI
9
👤 HR / People
7
🎧 Support
4
Summary
Decagon scores 3.9/5.0 on Glassdoor with a 3.7 work-life balance rating. Stripe scores 4.0/5.0 overall with a 3.6 WLB. That’s a 0.1-point gap on overall satisfaction.
Both companies share these culture values: Engineering-Driven, Strong Comp & Equity, Direct Product Impact. Decagon also emphasizes Ship Fast & Iterate. Stripe also emphasizes Learning & Growth, Transparent.
On the hiring front, Decagon has 95 open roles and Stripe has 490 open roles.