The man, who cannot be named for legal reasons, took the case to trial in the Victorian County Court, maintaining he was innocent.
He dropped his head as the jury on Tuesday returned their guilty verdicts to one charge of sexual assault and two counts of rape.
Prosecutors said he assaulted a younger woman at his Melbourne home in the early hours of March 24, 2023.
The woman was employed by the man in 2022 and she reconnected with him for more work opportunities the day before the incident, the jury was told.
She agreed to go over to his place on the afternoon of March 23 and they discussed work before listening to music, drinking wine together and using cocaine, prosecutors said.
The pair went to his friend's place to watch the football and she returned to her former boss's home sometime after 10.30pm, where they continued to use drugs and alcohol, the jury was told.
The woman became emotional while discussing a recent break-up and the man hugged her and said he would take care of her before kissing her.
The woman pushed her former boss away but he began touching her breasts, waist and buttocks.
She told him to stop but he said he couldn't because she was "so sexy", the jury was told.
The woman was holding a pillow and crying into it when the man raped her twice.
Defence barrister Dermot Dann KC argued the woman was lying and his client was innocent.
"It's screamingly obvious the foundation of this prosecution case ... Â is unsafe and unstable," Mr Dann told jurors in his closing address.
"It's so obvious you cannot rely on (her) evidence."
Prosecutor Matthew Fisher conceded there had been some inconsistencies in the woman's account but argued she spoke truthfully about what happened on the night of March 23.
"You should accept her as an honest and genuine witness," Mr Fisher said.
The jury began their deliberations on Friday after hearing 10 days of evidence.
They returned their guilty verdicts on Tuesday morning.
The man's bail was revoked upon the verdicts and he was taken into custody to face a pre-sentence hearing at a later date.
A hearing on whether to extend a suppression order over the man's identity and occupation will be held on Tuesday afternoon.
1800 RESPECT (1800 737 732)
National Sexual Abuse and Redress Support Service 1800 211 028
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