Prithvi Ramakrishnan is the co-founder and CEO of Promptless (YC W25), which builds AI agents that keep technical documentation current as software ships, updating docs from feature releases, support tickets, and engineering conversations.

Before Promptless, he was VP of Product and Engineering at Bond, a fintech infrastructure company acquired by FIS. He holds a BS in Computer Science from Stanford.

Does Your Documentation Survive an AI Assistant? A Hands-On Docs Audit.

Co-presented with: Manny Silva

Your customers are already asking AI assistants about your product. The assistants are answering from your documentation, and not always correctly.

This is a hands-on audit lab. Bring your own docs and find out what assistants actually say about your product. You’ll run retrieval and answer-accuracy tests against your real content, see exactly where it breaks, figure out why, and leave with a written audit of your own documentation and a prioritized list of what to fix first.

In this half-day workshop, you’ll learn how to:

Test what an AI assistant actually tells your customers about your product

• Spot the retrieval failures behind wrong answers (missing context, ambiguous headings, buried prerequisites).
• Tell content problems apart from structure problems, so you fix the right layer.
• Run a repeatable audit you can take back to your team and rerun each release.
• Use agents to remediate what you find, including in Flare and Oxygen toolchains.