Small information technology and management consulting businesses face increasingly contradictory strategic choices as they develop products and services for the marketplace. Building contextual ambidexterity is essential to the survival of small businesses as they seek to attain a desired balance of alignment and adaptability. Human Resource Management practices facilitate the development of ambidexterity within individuals thereby facilitating ambidexterity of the organization as a whole. Studies suggest that in order for an organization to be ambidextrous, its human resource management function also needs to ambidextrous. High-performance work systems are human resource practices designed to enhance the ability, motivation, and opportunity of employees with the overarching goal of attracting, retaining, and motivating human resources toward the completion of organizational goals. Based on Gibson and Birkinshaw’s concept of organizational ambidexterity, a qualitative case study of a small technology solution provider was conducted to explore the process by which CloudCo attempted to build contextual ambidexterity by implementing a high-performance work system. Findings show that executive management of small technology solution providers can build contextual ambidexterity and sustain a competitive advantage through the implementation of high-performance work systems but must overcome a series of important tensions to do so.