Hope this image will helps.
Cheers!
Yohan

Thanks, that is checked but the following flag is still not allowing him to sign in to work bench.  He is a former employee that we re-activated.  

Hi Please check for the Employee in the Employee Tab of the Company 543, i think there must be an expiration date for this employee. Remove this expiration date if the date is in the Past, then the check box will be Checked.

Thank you so much.   I have asked our HR and Finance team to remove as I do not have rights.