Sales is a profession that faces an inordinate amount of failure. When salespeople fail and face rejection from the customer, the consequences can be widespread and lasting. Perhaps, however, salespeople should not aim to prevent all sales failures, but instead anticipate and control the timing of when failure occurs in the sales cycle. Across three progressive studies, this research explicates the phenomenon of failing fast within a business-to-business sales context. The authors theoretically conceptualize a multi-dimensional salesperson failing fast construct—collection, interpretation, and action—and empirically test a process model by which these dimensions are sequentially linked together. The authors then study the focal relationship between failing fast and sales performance, contingent on individual-, organizational-, and environmental-level moderators. While the direct effect is non-significant, the finding is novel in that it shows certain forms of failure may not actually be a detriment to performance. The moderator analysis sheds further light on this relationship, revealing a mixture of accentuating and attenuating effects. This research collectively brings greater nuance to the study of sales failure and enables future scholars to understand the consequences, and even potential benefits, of failing early in the sales process.