Tim Bentley allegedly punched two men at the Ramblin' Rascal Tavern in Sydney's CBD while attending a gig on February 13.
Local pub band The Grand Union were due to begin playing when the 50-year-old allegedly attacked guitarist Stu Greenwood.
He is accused of assaulting another musician, John Flaws of Bloody Legend in the same five-minute window.
Rohin Sharma, The Grand Union's guitarist, told Nine newspapers the band was shocked by the alleged incident, which was part of a worrying trend of poor behaviour at live shows.
"We're here on our own time to give people a good night out and, like most local bands, these are self-funded passion projects that involve many hours of writing, rehearsing and recording," Sharma said.
"It's a sad indictment on Sydney's live music scene and points to an alarming growing trend of heckling and violence at live shows and bars."
Bentley appeared in Downing Centre Local Court in Sydney on Wednesday accused of two counts of assault occasioning actual bodily harm.
He is the vice-president of sales for Asia-Pacific at tech behemoth Abnormal AI, which was valued at more than $7.8 billion in August 2024.
The company's website says Bentley launched its operations in the region in 2021.
Abnormal provides security services to a quarter of the Fortune 500, representing some of the largest companies in the world.
Creating tools to stop employees falling for phishing emails is one of the services provided by the company.
Bentley's barrister Tim Lowe successfully applied for an adjournment in court on Wednesday to continue making formal representations with the prosecution.
The matter will return to court on May 4.
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