This chapter reports on and discusses an extensive interview conducted by the authors with the head of pre-sales at a hardware and software re-seller. The Pre-Sales division of the reseller provides advice based on end-to-end solution for IT infrastructure and technology management. Within the team there is expertise spanning a plethora of specifically defined technology areas to support end customers in the decision making process on their capital expenditure in IT equipment. Areas include Software licensing, Server infrastructure development, data storage and management, systems security, and networking infrastructure (and more). The business of being a re-seller may not initially strike the reader as being relevant to cybersecurity in general, and socio-technical matters at all, but we discovered the rather vital role that such an intermediary performs through their added value and corporate ethics. Specifically, this reseller’s team of customer service agents provide advice and referral to colleagues and end customers for subject-matter expertise as well, naturally, for opportunities to up-sell – specifically with that important core of any economy: Small and Medium-Sized Enterprises (hereafter SMEs) - usually defined as companies with up to 250 employees. In other words, the business both responds to requests for solutions from existing customers (pull) and actively engages with customers to grow awareness about, for example, security risks in order to sell products and services (push). The authors – drawing on a background of research in corporate resilience and SMEs (with a commercial background in the IT sector) were interested to learn from an individual with his finger very firmly on the pulse of SME cyber-security awareness, just what his view was on the general level of cyber-security awareness amongst SMEs and what his company offered in the way of assistance