Collaboration is a key driving force for a team's success. In this case study, we discuss the collaboration practices of the Design Team and a subset of product teams at Chatham Financial -- a financial risk management advisory and technology firm. The Design Team's collaboration workflow has four key elements surrounding the structure, cross-team communication, onboarding, and feedback that occurs both in team and cross-team collaborative partnerships. Each of the key elements leads to a unique set of challenges and opportunities for the Design Team. We analyze the current state of each element, their value proposition, challenges, and initiatives undertaken to make the collaboration practice more robust