Balesh Dhankhar posted fake job advertisements to lure women into his orbit before drugging them in or near his home.
The married IT consultant then groped and raped the women, filming his crimes for his future sexual gratification.
All the women were either unconscious or significantly impaired at the time of the abuse.
Police found an Excel spreadsheet recording his interactions with each victim, their personal details, and his assessment of their vulnerability and suitability for his plans.
In jailing Dhankhar for a minimum of 30 years on Friday, District Court Judge Michael King said he was unable to find any NSW case with a similar scale of offending.
The offender's conduct was "premeditated, elaborately executed, manipulative and highly predatory" and demonstrated his desire for sexual gratification came in complete and callous disregard of each victim, he said.
"This was an egregious sequence of planned predatory conduct against five unrelated young and vulnerable women over a significant period," he said.
Victim-survivor advocate Karen Iles credited the judge for recognising the impact on the victims.
One described how Dhankhar "has inflicted wounds on my soul".
"That is exactly why matters of sexual violence are such serious crimes," Ms Iles told AAP.
"They are horrific crimes of the most serious nature and in order to change attitudes, to change the behaviour, we need to have deterrence."
She said the size of the sentence would please Australian women, one in five of whom have been sexually assaulted at some stage in their life.
"As the Law Reform Commission found this week, less than one per cent of rape and sexual assault perpetrators ever face any type of legal consequence, and often those sentences are not custodial," Ms Iles said.
Until his arrest in 2018, Dhankhar was highly regarded among the Indian-Australian community, founding a satellite group of Prime Minister Narendra Modi's party and acting as a spokesman for the Hindu Council of Australia.
He also worked as a data visualisation consultant with the ABC, British American Tobacco, Toyota and Sydney Trains, having arrived in Australia as a student in 2006.
His presentation as a community-minded individual concerned with and active in improving the quality of life for others was "entirely inconsistent with his seriously flawed and predatory character" revealed in court, the judge said.
After preying on his fifth victim in October 2018, police raided his Sydney CBD unit and found date-rape drugs and a video recorder disguised as a clock radio.
A jury in 2023 found him guilty of 39 offences, including 13 counts of sexual assault.
Dhankhar continues to deny drugging the women or that sex was non-consensual, telling a report writer there was a "difference in how I interpret consent, to how the law sees consent".
His non-parole period expires in April 2053, backdated to the end of his trial.
Dhankhar will be aged 83 when his full sentence of 40 years ends.
1800 RESPECT (1800 737 732)
National Sexual Abuse and Redress Support Service 1800 211 028
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