This study aims to explore the influence of salespeople’s goal orientation and self-regulation mode on performance through sales ambidexterity and sales technology infusion (STI) in a sales technology ecosystem approach. Using a qualitative methodology in the form of in-depth interviews, this study involved salespeople from various industries to understand the relationship between goal orientation, ambidexterity, STI, and performance. The findings of this study identify two main groups of salespeople: skeptics, who show hesitation towards the full use of sales technology, and enthusiasts, who actively utilize technology to improve their performance and adapt to change. This study provides new insights into how sales technology can facilitate salespeople’s ambidexterity and offers practical implications for organizations to optimize technology adoption and ambidexterity orientation in order to improve sales effectiveness. This study also extends the literature on sales technology ecosystems by providing new perspectives on the impact of individual and organizational factors on salespeople’s performance in a B2B context.