One person who is FT Detention Officer and PT Deputy Sheriff: Overtime pay?

I'd like to know everyone's opinion on whether we would face overtime pay or other issues in the following situation:

If we hire an employee who is currently a full-time detention officer (oversees inmates in the jail) to also be a part-time deputy sheriff (investigate crime and arrest individuals) to work weekends, are we going to face overtime issues because the jobs are too similar? The employer and direct supervisor would be the same (i.e. the Sheriff).

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