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Notwithstanding the importance of small software firms, research focusing on understanding the growth challenges faced by their management is close to non-existent. By taking a life-cycle approach and focusing on managerial challenges, the aim of this paper is to analyze the growth process of small software firms. After forming a synthesis of possible growth challenges from relevant literature, the results are reflected upon case software firms using thematic interviews and questionnaires. According to the analysis of four software firms, managing human resources represents the greatest challenge for software services firms. Additionally, other challenges stem from competition and sales-related activities. Comparative analysis of the literature and the cases leads toward a theoretical conceptualization of growth challenges from small software firm’s perspective.