Automatable is not realizable
Most automation roadmaps are sorted by how easily a task can be automated. That is the easy question now, and it is the wrong one to sort by.
Sort instead by whether the value can be converted. Value converts through one of four paths: growth absorbed without hiring; a backfill avoided as someone leaves; redeployment to work with a measurable output; or a cycle-time gain that changes cash. An opportunity with no path and no owner scores zero, even if it is the most automatable thing on the list, even if it is the one the vendor is most excited about.
This one rule reorders almost every roadmap. It usually moves a boring, unglamorous piece of work to the top, because it has a clear path and a willing owner. Those are the ones that actually land.
Know your team’s number.
The estimator takes five minutes and gives you a defensible first figure you can take upward.