Go to SQLServer Agent / Jobs and create a new job. Add a new step of type 'Operating System Command (cmdExec)' and type in the path and name of the executable you want to run.
Be aware that the EXE will run on the server and the path will also relate to the server.
This can then be scheduled by adding scedules etc.
When you schedule a Job, it runs under the SQL Agent or SQL Server account. It will not see MAPPED drives. It will not be able to get to shares or directories on other servers if the account doesn't have permissions.
You can edit the Job and open the Step that executes the program. Click on the Advanced tab of the Job Step. Near the bottom of the dialog you'll see an output file. Enter a location of a file to write a log. You should be able to examine that log and find what is happening with the Job. Terry L. Broadbent FAQ183-874 contains tips for posting questions in these forums.
NOTE: Reference to the FAQ is not directed at any individual.
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