The online role play simulation as described in this article addresses critical skills as identified by practitioners and includes background materials, buyer and seller profiles, a sale/no-sale decision matrix, as well as a grading rubric, thereby facilitating a variety of selling scenarios. Both the buyer and the seller have integral roles in the outcome of the sales process in this role play, with as much emphasis placed on either role, enabling a more in-depth learning opportunity for students to clearly understand the buyer's motivations. This interactive pedagogical online tool enables instructors to align their sales curriculum content and pedagogy with practitioners' needs, while facilitating the learning experience for the professional selling student by simulating the role stress and ambiguity of the sales profession and to actually employ adaptive selling techniques.