JECT.AI is a research-based digital product designed to support news editors and journalists to be more creative when discovering new angles and voices to incorporate into the content of news stories under development. It implements different artificial intelligence (AI) algorithms to deliver interactive and intelligent support to individual journalists and editors in response to topics of interest that they enter or highlight. Whilst studies demonstrated the potential effectiveness of the product in newsrooms, discovering how to deliver its AI in newsrooms for longer-term use has proved to be more challenging. This chapter summarises three sequential pivots in the design and positioning of JECT.AI that were undertaken to overcome barriers to the regular use of the product’s AI technologies in newsrooms. Although each version of JECT.AI was offered to journalists and newsrooms, different barriers to its uptake were encountered. The chapter then describes the most recent version of the product, which seeks to deliver creative insights about news stories relevant to journalists in different ways. Each experience and subsequent pivot have the potential to inform the uptake of other co-creative AI technologies, and especially generative AI technologies accessed via chatbots, in newsrooms and other workplaces that require regular creative thinking.