Most teams start automating in the wrong place. They pick the task that annoys them most, which is rarely the task that costs them most. The two feel identical from the inside and they are not the same thing at all.
The jobs worth doing first share a shape. They happen every day rather than every quarter. They follow the same steps almost every time. They move information from one system into another without changing it much. And when they are done late, something downstream is late too.
Intake is almost always first. Whatever arrives from outside the business — a call, a form, an email, a photo of a purchase order — someone is reading it and retyping it somewhere else. That retyping is the single most common automation we build, and it is usually the one that pays back fastest.
Scheduling comes next, then follow-up, then the daily reconciliation of two systems that disagree, then reporting. Reporting is last on purpose: it feels the most impressive to automate and changes the least about how the week actually goes.
The useful exercise is not to rank tasks by how much you dislike them. It is to walk one week and write down every moment somebody moved information without deciding anything. That list, in order of how often each line repeats, is your roadmap.