What would you do if you were tasked with developing a new categorization for your company’s products and services? Under the best circumstances, this is a hefty undertaking; but, to add to the complexity, consider that your company is a massive hiring website with varied products and services, and they want to change the names of their products and services based on UX research that revealed the names are confusing. So, now you are tasked with establishing a new categorization before these new names are developed. This task was a recent research challenge of ours. In this presentation, we will discuss how we utilized card sorting and treejack testing to iteratively test categorizations. We will share our methodology and discuss how we overcame usability and technical limitations of the Optimal Workshop treejack tool. We will share our hard-earned tips and tricks for the audience to utilize in their own research.