This case study explores how a series of customer site visits to two international service centers drove design recommendations for a chatbot building platform that could encourage positive agent-chatbot collaboration. The first part of the case focuses on the research undertaken by a team of user experience practitioners at the enterprise software company Salesforce. The team used contextual inquiry and group interviews to better understand the daily experience of customer service agents and service teams in search of ways to responsibly implement automation tools like chatbots within a service center environment. The second part of the case study highlights how the UX team applied these learnings into specific product recommendations and developed a set of principles that could drive the product forward while remaining empathetic and supportive of customer service agents.