Fluid "systems of assessment" increase college and career readiness for all students, create a more equitable PK-16 school-to-work transition, and foster collaboration across stakeholders. This study explores how a local comprehensive assessment system (CAS) offers a mechanism for matching high school graduation requirements with criteria for post-secondary success in a globalized economy. It establishes the critical role personalization and proficiency-based learning play when phasing out rigid academic programming of the 20th century. The systems change necessitated by coordinating a local comprehensive assessment system promises to also help narrow the middle-skills labor market gap. CAS provides the infrastructure from which flexible pathways develop all learners' potential to succeed in the 21st century. As a result, job placement rates become a key data point for determining the effectiveness of a learner-centered school culture. When a supervisory union / district's internal processes are tightly aligned with the expectations put forth by Vermont's "Educational Quality Standards" ("EQS") Section 2123.2 Development and Implementation of Local Comprehensive Assessment System, then an innovative state-level accountability model is equipped to continuously evolve. Participants report the language of "comprehensive local assessment system" has not been a key feature in the implementation of Vermont's "EQS" and/or "Act 77: Flexible Pathways to Post-Secondary Success." Grounded theory techniques were utilized to identify themes, while Vermont's mandated state policy was the central phenomenon of analysis. The selected sample targeted sixty-eight individuals who were directly involved with the implementation of this enabling state-policy. Findings indicate participants view the proposed cultural change as a step toward more equitable assessment practices. However, in the absence of distributive leadership, practitioners report their capacity to alter organizational behavior continues to be undermined by a management mentality. Additional research is recommended to further define what high-quality leadership does and how that can influence the systemization of a learner-centered school culture. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://bibliotheek.ehb.be:2222/en-US/products/dissertations/individuals.shtml.]