Digital Promise and Global Education Exchange Opportunities (GEEO) established a partnership in May 2020 to support and expand educator professional learning and use of technology in Puerto Rico through coaching and micro-credentials. Together, the organizations identified an opportunity to address the gaps in coaching structures and pilot a coaching model to support the powerful use of technology in schools. From January-June 2021, GEEO, with the support of Digital Promise, launched a 6-month coaching pilot with 10 schools across Puerto Rico. As part of the pilot, school leaders, coaches, and teachers engaged with micro-credentials to support their professional learning journey around systems change, coaching, and technology. The pilot was based on the Challenge-based Coaching Model which was developed through Digital Promise's work on the Dynamic Learning Project. The objective of the pilot was to help coaches work with teachers to enhance their technology use and tackle instructional and professional challenges using innovative strategies. This report represents the results and findings from the coaching pilot. [This paper was co-produced by Global Education Exchange Opportunities (GEEO), and funded by the Puerto Rico Department of Education.]