South Bend Mayor Pete Buttigieg is set to attend a fundraiser with a top Uber executive just weeks after expressing solidarity for drivers protesting the ridesharing company.

The Indiana Democrat is one of 14 presidential candidates who will descend on San Francisco this weekend for the California Democratic Party State Convention. Between attending an SEIU California Democratic Delegate breakfast on Saturday morning and addressing convention goers later that afternoon, he will headline a fundraiser in Oakland hosted, in part, by Uber executive Chelsea Kohler, the rideshare company’s director of product communications.

It is a dissonant move for a candidate who fewer than three weeks ago voiced his support for striking Uber drivers demanding an end to pay cuts and a drivers’ bill of rights ahead of the ridesharing company’s initial public offering on Wall Street.

“I’m standing in solidarity with @_drivers_united and all those striking across the country today for livable wages, more job security, and regulated fares,” Buttigieg tweeted on May 8, the day of the international rideshare strike.“We must raise the labor standards in this country.”

Buttigieg’s presence at the fundraiser illustrates the fraught position he occupies as one of the most tech-friendly candidates in a primary campaign where candidates are trying to demonstrate their pro-worker bona fides. He has deep ties to Silicon Valley heavyweights and even went to college with tech titans such as Facebook co-founder Chris Hughes, who has long supported Buttigieg’s political career. Yet Buttigieg is also a ubiquitous presence alongside striking workers at picket lines. In April, he backed workers employed by the Stop & Shop grocery chain in Malden, Mass., and recently cut a video supporting McDonald’s employees’ fight for a $15 minimum wage and a union.

Buttigieg’s support for striking Uber drivers seemed to echo those past efforts. Among other demands, the Drivers’ Bill of Rights would include Uber and Lyft’s “recognition of our independent, driver-led organization, to negotiate on behalf of drivers.” On his policy page, Buttigieg advocates for a “new Wagner Act to support the role of organized labor and defend the right of workers to organize.”

“Our nation’s middle class was built by organized labor, and rising attacks on labor have led to the middle class becoming more and more vulnerable,” according to the page. Buttigieg also says he supports a $15 minimum wage.

But Buttigieg also hasn’t gone quite as far as his fellow nominees in coming down hard on Silicon Valley, chiefly Sen. Elizabeth Warren (D-MA), who has proposed breaking up tech giants such as Google. At a New Hampshire CNN town hall in April, Buttigieg said that antitrust law "as we know it has begun to hit its limits with regulating big tech companies. It’s not designed to handle some of these tech companies where there’s actually no price at all. The product is made free, or at least it’s free on its face. We’ve learned in part because of the way our data are used by these companies that nothing is actually free.”

Chris Meagher, Buttigieg’s national press secretary, declined to comment. But an organizer with the Los Angeles-based drivers’ association told The Daily Beast that the candidate’s decision to fundraise with an Uber executive was untenable with his support for the contracted drivers.

“We appreciate Pete Buttigieg’s support, and this is an instance where there are two clearly opposing sides and he must pick one,” emailed Brian Dolber. “Passenger fares either go to the hardworking drivers or the multi-billion dollar companies—and right now Uber/Lyft are regularly taking 50%+ of what the passenger pays while countless drivers are homeless or living in poverty. Standing with drivers, means standing against the executives who have been ruthlessly slashing driver pay year after year.”

Other tech executives will be at the Saturday fundraiser for the South Bend Mayor, including Chris Cox, Facebook’s former chief product officer; Scott Kohler, Google’s corporate counsel; and Clay Bavor, Google’s vice president of virtual and augmented reality. Tickets for the event run from $25 to $2,800.

Dolber, who is also an assistant professor of communication at California State University San Marcos, said the fault line exposed in this case could be a harbinger of what’s to come for the Democrats in 2020.

“Worker movements and popular criticism of Silicon Valley suggest that the Democratic Party's long standing connections to Big Tech may prove to be a problem for their base,” Dolber said. “Political candidates will have to reconsider a strategy that triangulates between impoverished workers and billionaire bosses. The conversation around the gig economy and inequality, as well as algorithmic management, surveillance, and automation is shifting the political terrain.”