Influencer marketing is an emerging technological disruptor for marketing across a wide range of industries. This tactic allows companies to promote products in a more organic, trust-affirming manner compared with other forms of paid advertising. As the use of influencer marketing is rapidly growing, marketing educators have a unique opportunity to prepare students to perform this in-demand marketing skill. This article outlines a classroom exercise, called the Matchmaking Activity, which introduces the concept of influencer marketing, provides hands-on experience, and encourages critical thinking to solve a simulated marketing dilemma. The end goal is for students to gain confidence that can be applied to a real-world marketing environment. To assess the effectiveness of the Matchmaking Activity, the exercise was conducted with students in digital marketing classes. Based on findings from a post-activity reflection survey completed by students, the Matchmaking Activity results in the achievement of several desirable learning outcomes. Ideas for adapting this exercise for use in a variety of other marketing courses are also provided.