GREAT TOPIC!
The first thing IMO is to capture all the virtual dead customers, those customers that have churned. (You may need to develop a written definition for the moment of churn even if you have contract renewals) Once you have this group, you can start identifying common characteristics that precede the churn. None of the below is one and done, it iterates over time, Except for #0… maybe. 0. Define the moment of churn
This is not a pitch! But... if you were Sales or Marketing, you would have already hired someone to help you with this. There aren't an infinite number of reasons customers leave companies. It will take months if not years to compile this from scratch - you can make progress, which is great and should keep your boss happy - but factor in the number of customers you may lose in the meantime. I suggest you find a professional who has done it. They should be able to provide you with a high level assessment of what it would take to get you up in running and working through the iterations that are required. Very difficult to do while you are also dealing with the demands of your day job! DO NOT BUY SOFTWARE until you do this process work!!
Hope this helps, good luck in 2021!
Jordan,Fantastic point of view! I always love the "big picture" as a place to start. It truly is as simple (and complicated) as "show the business impact" of these actions. Then, the conversation is focused on how we can improve that impact. Instead of trying to justify the cost of headcount.
Super insightful approach here.