Hard Earned Lessons for Dev Tool Startups

In this episode, Diamond Bishop shares his fascinating journey through AI, machine learning, and enterprise software, from working at Microsoft (Cortana), Amazon (Alexa), AWS, and Meta (PyTorch) to founding Augmend, an AI-driven DevOps knowledge assistant, which Datadog later acquired.

He dives deep into building AI-powered enterprise products, the challenges of selling into large organizations, and why AI-driven automation is the future of DevOps and security operations. Diamond also unveils Bits.ai, Datadog’s intelligent AI assistant designed to automate on-call incident resolution, debugging, and code error fixing.

For founders, product leaders, and AI enthusiasts, this episode is packed with lessons on enterprise GTM (Go-To-Market) for Developer Tools, AI-driven automation, and the future of software engineering.

Key Topics Discussed:

1️⃣ The Evolution of AI & Machine Learning

2️⃣ Founding Augmend: AI for DevOps Knowledge Sharing

3️⃣ The biggest challenges for Dev Tool startups

4️⃣ Bits.ai: The AI Assistant for DevOps & Security

5️⃣ Lessons in building with Gen AI & GTM Insights

Who Should Listen?

✅ AI/ML Engineers & DevOps Professionals – Learn how AI-driven automation is transforming workflows

✅ Tech Founders & Enterprise GTM Leaders – Get real-world insights on selling AI to enterprises

✅ Investors & AI Enthusiasts – Understand the next wave of AI-powered enterprise automation

Resources & Links:

🔗 Follow Diamond Bishop on LinkedIn

🔗 Datadog Bits.ai (Private Beta)

📢 Enjoyed this episode? Don’t forget to subscribe, rate, and share! 🚀

This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit veenormous.substack.com