While many career centers are expanding digital learning opportunities, there are continued barriers in scaling recognition and tracking completion in meaningful ways. This roundtable will explore how one team designed and implemented an automated certificate workflow that delivers completion certificates to students after finishing asynchronous career development modules. Participants will engage in a discussion on tools, integrations, and process design, including platforms like Qualtrics and PDF generation solutions, to better understand how to streamline credentialing while reducing manual work. Attendees will share their own approaches (or challenges) with issuing certificates, micro-credentials, and tracking engagement. Together, we will identify scalable strategies, common pitfalls, and opportunities to enhance student motivation and program visibility through automation.