Decagon
Small (~210)
Twilio
Large (~5,500)
Best For
Decagon
Best for: Builders who want to ship AI customer support agents directly to F500 customers with technical founders deeply involved
Twilio
Best for: Professionals interested in Twilio
Ratings
DecagonTwilio
3.9
3.9
Overall
3.7
4.1
Work-Life Balance
3.8
4.0
Culture & Values
3.2
3.9
Comp & Benefits
3.7
3.7
Senior Mgmt
3.7
3.7
Career Opps
👍 75% Recommend
👤 85% CEO Approval (Jesse Zhang)
👍 78% Recommend
👤 82% CEO Approval (CEO)
Culture Values
Decagon only
🚀 Ship Fast & Iterate🎯 Direct Product Impact
Twilio only
🌐 Remote-Friendly⚖️ Work-Life Balance🔓 Open Source🌱 Learning & Growth
Shared
⚙️ Engineering-Driven💎 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
Twilio
- Genuine remote-first flexibility with excellent work-life balance
- Strong compensation, benefits, and engineering-driven culture
- Frequent reorgs and leadership changes create uncertainty
- Culture has shifted from creative builders to more corporate, profit-driven focus
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.
Twilio
Twilio — check Glassdoor for detailed reviews.
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
Twilio — 143 jobs
💼 Sales / GTM
44
💻 Engineering
43
📋 Product
8
🧠 ML / AI
7
📣 Marketing
6
⚙️ Operations
3
📊 Data
2
🎨 Design
2
💰 Finance
2
👤 HR / People
2
⚖️ Legal
2
Summary
Decagon scores 3.9/5.0 on Glassdoor with a 3.7 work-life balance rating. Twilio scores 3.9/5.0 overall with a 4.1 WLB. They’re tied on overall satisfaction.
Both companies share these culture values: Engineering-Driven, Strong Comp & Equity. Decagon also emphasizes Ship Fast & Iterate, Direct Product Impact. Twilio also emphasizes Remote-Friendly, Work-Life Balance, Open Source, Learning & Growth.
On the hiring front, Decagon has 95 open roles and Twilio has 143 open roles.