Onboarding in the AI Era: My First 100 Days at Ramp

▤ Summary

The author recounts their first 100 days at Ramp and how they constructed an AI-native onboarding system to speed new hires. They built a continuously updated "company brain"—an Obsidian vault ingested and used by models like Claude—to centralize meeting transcripts, documents, Slack discussions, and customer feedback. They complemented the vault with automated meeting capture (Granola), a small markdown-based skills library for agents, a dynamic product roadmap, and daily briefings to keep context fresh. The article argues companies will get more value from investing in a trusted, reusable context layer than from deploying many isolated AI agents, and invites others building similar systems to share experiences.

▦ Linked Companies

Ramp

$1B+