Small and Medium Enterprises (SMEs), as well as micro teams, face an uphill task when delivering software to the Cloud. While rapid release methods such as Continuous Delivery can speed up the delivery cycle: software quality, application uptime and information management remain key concerns. This work looks at four aspects of software delivery: crowdsourced testing, Cloud outage modelling, collaborative chat discourse modelling, and collaborative chat discourse segmentation. For each aspect, we consider business related questions around how to improve software quality and gain more significant insights into collaborative data while respecting the rapid release paradigm.