Background Blackboard signed up for Kloudless in order to move beyond its inherited, bespoke integration strategy. First, here’s some background on the company. Blackboard supports both educators and students in schools, universities, and higher education institutions. Founded in 1979, Blackboard is among the first to pioneer the space, exploring and innovating new methods to enable technological methods of instruction. Blackboard’s suite of educational products equips teachers and administrators with the tools to ensure that their students have access to a safe, secure, and engaging place to learn. With over 90 million users across thousands of institutions worldwide, Blackboard needed an integrations solution that was effective, secure, and scalable. Students and educators share files in and out of the classroom. Blackboard’s flagship product, Blackboard Learn, is an educational platform built for both teachers and students to communicate and collaborate outside of the classroom. Yet even with the full suite of platform features, Blackboard Learn was still just one of the many software services found in the average educator’s technology stack. Educators and students alike would store their files, assignments, and other assets in any number of popular cloud storage services, such as Google Drive, Dropbox, and Box. Blackboard’s users wanted to be able to access, upload, and edit those files within Blackboard’s own platform without their workflow being interrupted. The Challenge Version upkeep for multiple cloud storage services proved challenging. The product team at Blackboard had inherited a bespoke integration—Dropbox—and initially sought to build out the rest of the popular file storage services the same way: internally. They started with Microsoft OneDrive, a popular request, but soon ran into a number of issues. To their surprise, the initial integration was not what required the bulk of their time and effort: it was the maintenance of the integration that proved to be a headache. Over three years of maintaining their bespoke integration, Blackboard received more than 600 JIRA tickets and racked up approximately 8,800 hours towards OneDrive support alone. Unpredictable changes that Microsoft made to the OneDrive API would interrupt Blackboard’s automated scripts, breaking their meticulously designed integration infrastructure. Each issue would remain open for anywhere from two to four weeks before it was fully resolved. It was starting to distract engineering attention away from the core product, and even began to hurt the confidence that their customers and users—especially the newer ones—had in the Blackboard platform. It was becoming painfully clear that Blackboard needed to find a scalable solution that did not involve building and managing each integration in-house.