Part of the problem is that to effectively automate a task or series of tasks you need to fully understand what is being done. The person currently doing this

Part of the problem is that to effectively automate a task or series of tasks you need to fully understand what is being done. The person currently doing this knows what they are doing (you would hope), and may understand why they are doing it (this is not guaranteed). In many cases, what somebody does (and why) is not documented, or if it is the documentation is most likely out of date and inaccurate. To effectively automate a task, you need to fully understand what needs to be done as well as have the skills to do the actual automation. Getting somebody in who is unfamiliar with the job, can work, but in most cases you will end up with an off the shelf system that has been customised to perform the original task but come with a large overhead of maintenance that may take more work than the original task. My suggestion would be that rather than get an outsider to create the automation tools, up-skill and authorise the staff doing the work now to allow them to gradually automate the process. Make sure you make it worth their whiles to automate.