The Computer Information Systems Learning and Technology Sandbox (CIS Sandbox) opened as a collaborative learning lab during the fall 2011 semester at a New England business university. The facility employs 24 student workers, who, in addition to providing core tutoring services, are encouraged to explore new technologies and take on special projects to support or enhance the day-to-day operations of the CIS Sandbox. Doing so creates a culture of entrepreneurship and encourages innovation among the student workers and their peers. This paper follows up on previous results by describing a student-initiated development project to rewrite a card-swipe desktop application that tracks student usage, as an integrated suite of web and mobile apps. The paper presents the architecture of the new system along with perceptions from the student developers around their motivations to contribute to the CIS Sandbox technology infrastructure. Initial use of the prototype suggests it will improve productivity among tutors and provide faculty with easier access to tutoring data.