Information Technology (IT) departments within Small- and Medium-sized enterprises (SMEs) face challenges that are significantly different from larger corporations with greater resources and higher levels of IT staffing. From resource constraints to nonexistent training budgets, IT personnel are constantly striving to do more with less. This Research-in-Progress investigates the challenges and opportunities of IT specialists working in micro-firms, the lowest end of SMEs. Interviews will be used to explore this topic, developing a framework of salient factors and key indicators. Although this general topic has been studied for nearly three decades, rapid advancements in technologies and corporate pressures have created radical changes that directly impact this sub-strata of the IT world. A survey will be developed and distributed using a social networking method; results of analysis will be used to evaluate the research propositions and to assess the primary antecedents contributing to IT success and job satisfaction in micro-firms. The research contributions will increase theoretical knowledge and provide insights for both IT specialists and executives in these business settings.