Jesse Seldess, the documentation lead at Pinecone, has restructured the company's documentation approach to prioritize user expectations over internal product hierarchies, enhancing ease of use for new users. By leveraging AI tools like Claude Code as a peer reviewer, Jesse has streamlined content optimization, making documentation a self-serve resource that reduces the need for human interaction and supports business scalability. He emphasizes hiring technical writers who can think from a user's perspective and collaborate across teams to produce content that meets real developer needs. Jesse's method includes identifying user goals through personal testing, competitor analysis, and stakeholder collaboration, focusing on reducing friction and increasing clarity for users. His approach highlights the importance of organizing information around user context and using AI as an aid in refining documentation, rather than generating it entirely.