Embodiments relate to systems and methods for generating a synchronous sales stack for a customer dialog. A user can visit a Web site and load selections into a checkout basket to prepare to purchase desired products and/or services. The user can select a live chat feature, which invokes an instant message, audio or video dialog with a sales representative. The sales representative can initiate a synchronous sales stack with the user, by which the user and sales representative can share a common view of purchase selections and potential alternatives or add-ons to the selections, as they are made. The customer and sales representative can continue their dialog as possible selections are explored, and the resulting sales stack is updated in real-time. When the user is satisfied with their selections, the sales stack can be stored as the customer's finalized checkout basket and the transaction can be completed.