Last quarter, my team at a mid-sized workflow automation tool set out to add a native AI assistant to our web app. Our goal was to let users ask questions about their custom workflows and get targeted, context-aware help instead of sifting through our static help center. Our first pass used a generic third-party chat widget, but it could only pull from public documentation and couldn’t reference a user’s own saved workflow data. It felt disconnected from the actual work users were doing in our app, so we scrapped that approach and started researching integration options.