The study addresses research gaps on methodologies for implementing software systems into Small to Medium-sized Businesses (“SMEs”). Clarification of how the implementation of Xero™ accounting software and WorkFlowMax™ information management software (“WFM™”) was provided to an SME, as well as the impacts of changing software systems on an SME. An evaluative case study was carried out on a small business in New Zealand, over a period of six months where this software had recently been implemented. Interviews with three SME staff members and a senior member of the software vendor, plus participant observation showed that there was scope for significant improvements to be made on both sides. For the vendors, recommendations from this case study include better management of SME expectations of software capability; increasing time spent with the client; and providing greater clarity around the scope and limitations of training provided. For the SME, recommendations from this case study include: identifying an internal champion with effective communication skills and/or spreading championship roles between more than one staff member; providing greater transparency during planning stages of software adoption combined with opportunities for staff to discuss their user needs; and greatly increasing the frequency of minuted meetings with all company administrators.