A rise in mental and emotional health made companies like this participant have an instantaneous value proposition, however the demand highlighted competitors to come to the surface. Communicating value propositions with customers for long-term success was not previously as strategic, where the team needed to revisit skills on how to establish value proposition across multiple stakeholders and departments within a district or organization. This in addition to funding now not as available as during the pandemic, the time for Customer Success to expand as sales-enabled contributors and leaders for expansion growth, was more prevalent to building internal capacity. While some of the existing team members and leaders had prior customer success, expansion, and/or SaaS experience, a number of team members were transitioning teachers or former customer support staff within a Customer Success role. The expansion of the team including the revenue-owning responsibilities, left a knowledge gap of leading difficult conversations and goal setting. The team needed to become streamlined in how to best serve customer outcomes and their company’s best practices by starting conversations early about expansion/renewal, proposing solutions on outcomes or needs, all while building trust to form deeper relationships and help navigate through education politics that may occur.