This interactive workshop demonstrates Gannon University's successful transition from Managed Hosting to the Software-as-a-Service (SaaS) deployment option in under 60 days. Attendees will chart their own plan in a project workbook as the presenters detail the process. Similar to sailing in unchartered waters, comprehensive planning and team-building enable a smooth transition. The presenters will illustrate how to maximize the partnership with Blackboard Technical Project Management to sail through a successful launch of the SaaS deployment. Attendees will learn to identify key stakeholders or crew and their responsibilities, map key processes, and coordinate events for limited disruption and maximizing success. Discussions and examples include integration of university resources and people as well as the process and timing of pre- and post-testing. Attendees will walk away with draft plans they can use to implement their own projects. This plan will analyze internal strengths and weaknesses, opportunities and challenges, and prospective resources. Participants are eligible to win door prizes throughout the session!