San Francisco native son Marc Benioff has long fostered an image as a progressive and benevolent billionaire. The Salesforce CEO is known for giving millions to children’s hospitals and advocating fiercely for taxes to fund homeless services in the city. 

But among even casual observers of social media, it’s hard not to notice a change in the persona he has been projecting in recent months. 

Autism Capital, a popular right-wing Twitter account often reposted by Elon Musk, described it using an alt-right term of praise for people who are “un-woke”: based Benioff. 

Amid dozens of posts about Salesforce’s new Agentforce platform, Benioff has positioned himself and his interests within the MAGA orbit, praising President-elect Donald Trump’s associates like Musk and Marc Andreessen, and touting Lex Fridman’s interview with Argentinian president Javier Milei, a right-wing populist and social conservative derided by the left and idolized by the Trumpian right. 

It’s unclear whether Benioff’s tonal shift represents a sincere change in his politics or a strategic business move. Benioff did not respond to a request for comment. 

What is clear is that he joins a cadre of Silicon Valley leaders who have given up their resistance to Trump and are pragmatically toeing the line, if not taking public victory laps, following the election. 

Amazon founder Jeff Bezos, who clashed with the president during the first Trump term, said this week that he’s optimistic about the second. And despite Trump’s lawsuit against Facebook in 2021 and other confrontations, Mark Zuckerberg dined with the president-elect at Mar-a-Lago. A representative said the Meta CEO is seeking an “active role” in the administration’s tech policy. 

These tech leaders appear to be following Apple CEO Tim Cook’s playbook for dealing with Trump during the first term, which included cultivating a personal relationship. Other executives are trying the tactic, according to reporting from the Wall Street Journal, especially as their companies face regulatory scrutiny and amid fears that Trump will deploy the power of the government against his political rivals. 

“I think anyone who has large-scale financial interests and government contracts clearly is thinking about their positioning in the next two to four years,” said Christin Evans, a San Francisco progressive advocate who has stayed in touch with Benioff since they worked together on the Proposition C homelessness tax. 

Salesforce’s involvement with the government has dramatically increased since Trump’s last term. The company has quadrupled its contracts with U.S. government agencies, landing at least 1,443 from 2017 to 2022. For context, Salesforce had more government contracts than Google in 2022 but fewer than Microsoft and Amazon. 

“We have Trump in the White House, we have a GOP-dominated House and Senate, and GOP-dominated Supreme Court,” said Evans, who owns two small businesses in the Haight. “I think smart people read the room.” 

In 2018, Evans convinced Benioff over a late-night Twitter DM conversation to support Prop. C, a ballot measure to raise taxes on big businesses to fund homeless services in San Francisco. Benioff became the measure’s face and funder, providing the campaign with $8 million of his own and Salesforce’s money. He publicly sparred with fellow tech billionaires like Jack Dorsey of Twitter, who opposed the measure. 

Benioff often cites his grandfather Marvin Lewis as inspiration for his civic-mindedness and desire to serve “stakeholders” instead of “shareholders.” Lewis was a San Francisco supervisor known for his efforts to build BART and fight poverty and homelessness. 

Benioff has taken political stands at Salesforce. In 2015, the company cancelled events in Indiana after the governor signed an anti-gay bill into law. In 2019, Salesforce banned use of its technology by customers who sell certain firearms. And after the Supreme Court overturned Roe v. Wade in 2022, Benioff told Salesforce employees that the company would help them access reproductive care. 

Benioff, whose net worth is estimated at more than $11 billion, and wife Lynne have given hundreds of millions to causes that fight homelessness and support public health and the environment. Benioff has said he isn’t a Republican or Democrat but views himself “very much just as an American” committed to social justice.

Jennifer Friedenbach, executive director of the Coalition on Homelessness, got to know Benioff during the Prop. C campaign and continues to update his team on the measure’s progress. 

“He was really supportive of this idea of taxing the rich and housing the poor, and was really helpful in that campaign both financially and in speaking out,” said Friendenbach. “I don’t think this has changed at all, because he’s still talking about the success of Prop C.” 

But it was in an exchange about Prop. C that Benioff gave one of the earliest hints of his evolving public politics. 

In July, Musk called out Benioff for supporting the measure, calling it a “crazy gross receipts tax” that “makes it impossible for financial companies to operate in San Francisco.” 

Benioff responded by falling in line. “I absolutely agree with you it should be reshaped as it is circa 2018,” he replied. “The world has changed. Let’s change it.” However, Benioff has defended Prop. C in exchanges with critics that followed. 

Three months later, Benioff took to X to shame Kamala Harris for rejecting Time magazine’s requests for an interview. (Benioff bought the publication in 2018.) Following Trump’s win, Benioff offered hearty congratulations for the “remarkable achievement.”

“This has now become a time of great promise for our nation, and we look forward to working together to drive American success and prosperity for all,” Benioff posted to X. 

Later that month, Benioff celebrated Joe Rogan’s interview of venture capitalist and Trump ally Andreessen, calling it a “must-listen” from one of tech’s “great leaders.” 

The shift has won Benioff plaudits among some politically aligned influencers. 

“You’re exploring new perspectives, inch by inch aligning with new narratives, and doing it in such a way that doesn’t compromise your businesses and prior relationships. We want to give you credit,” Autism Capital said.

But other groups long aligned with Trump and his movement have called out what they consider opportunism.  

Joe Lonsdale, venture capitalist and co-founder of Palantir Technologies, accused Benioff of being “a spineless weasel” after the Salesforce chief called Musk “the Edison of our era” who could “revolutionize government through DOGE,” referencing Trump’s planned Department of Government Efficiency, to be helmed by Musk and Vivek Ramaswamy. 

“He now sees which way power is going, but until he apologizes, fires radicals, and cleans up his own mess, should be kept far away from this admin @elonmusk,” Lonsdale posted on X.