For years, a Google search for “tech” and “homelessness” in San Francisco would invariably be populated by various rants and open letters from startup founders and other entrepreneurs decrying the “riff-raff” and “degenerates” they were forced to encounter on their streets on their way to work.

These tone-deaf tech bros came to define the tenor of San Francisco’s second dotcom boom, fueling frosty relations between an influx of wealth and a city left ravaged by economic disparities. The common narrative was of Versailles on the eve of the revolution – anti-gentrification protests against tech buses, pointed flyers accusing tech workers of ignoring the suffering around them, sidewalk graffiti declaring that “Queers hate techies”.

“There’s still a lot of antagonism and conflict between tech and non-tech people in the city,” said Jeremy Pollock, a former tech worker and member of the League of Pissed-Off Voters, a progressive political activist group in San Francisco. “You see themes of people railing against tech for ruining the city and you see a lot of tech workers feeling ashamed of working in tech and uncomfortable being public about it. We’ve seen it in the past, with the league, as we try to do outreach and pass out literature at the tech bus stops. There’d be a lack of eye contact.”

As the US prepares for crucial midterm elections on Tuesday, a measure on the ballot in San Francisco has rapidly become a test of whether the tech industry can locate its moral compass.

If it passes, Proposition C would lead to a tax on the biggest tech companies to fund a solution to homelessness in the city.

Tech leaders like the Salesforce CEO, Marc Benioff, and the Twitter CEO, Jack Dorsey, have helped make homelessness a matter of conscience for the industry with their very public battles over the proposed tax, which would raise an estimated $250m-$300m in additional revenue for homeless services. The fight is about more than just a ballot measure for tech and the city where it made its wealth.

To locals, tech workers, and those who identify as both, Proposition C is a reckoning for the tech industry as a whole. It’s the question everyone from the entry-level engineer to the billionaire founder must find a way to answer: where does the industry stand when it comes to civic engagement and social responsibility?

“That’s the question that’s on the top of everyone’s mind,” said Evan Owski, a LinkedIn engineer who stood outside the Square office on Market Street one recent morning, holding a sign stating: “CEOs don’t speak for us”.

“Some people within the tech industry are very supportive of Prop C, and others are really fighting against it and spending a lot of money against it,” he said. “It’s become this kind of wedge issue within the tech industry. Where do you stand on this massive wealth inequality in this city, where you have these multibillion-dollar companies? Are they doing enough to address this inequality that we’re seeing on our streets?”

If approved by voters on 6 November, Prop C would implement an average 0.5% gross receipts tax for companies with revenues over $50m, an amount the measure’s supporters say is negligible for the companies affected but critics say will drive business from the city in the long run.

The additional funds raised by the measure would go directly toward providing housing, rental assistance, mental health services and shelters for the estimated 7,500 who are forced to sleep on the sidewalks each night – a humanitarian crisis fueled in part by the tech boom contributing to rising housing costs.

“This is a critical moment where I think Prop C kind of illuminates who is willing to be a San Franciscan and actually support our local services,” Benioff told the Guardian.

The Salesforce CEO has led the charge for the measure, donating $7.9m to the Yes on C campaign and calling out his fellow billionaires for donating to the effort against it. In an op-ed for the New York Times, he wrote: “Business must have a purpose beyond profits” that “can, over time, benefit both stockholders and stakeholders”.

“I think this is the first time I heard the leader of a big technology company talk about their responsibility as a citizen, as an industry, to their community,” said Rachel Coldicutt, CEO of Doteveryone, a London-based thinktank that advocates for responsible and equitable technology.

“This is starting to feel like a real moment of change. It’s not like Marc Benioff is talking about a product or a business choice. This is something that is really relatable and is really easy to take the high ground over.”

Coldicutt believes that the latest iteration of the tech boom was initially optimistic in that it was centered around the internet, which was supposed to be for everyone and not just the powers that be. That’s why it feels especially disappointing when the industry behaves in a business-as-usual manner.

The tech workers who have taken up the cause of Prop C often point out at rallies that “new money looks a lot like old money” because corporate greed has persevered in an industry meant to disrupt the old ways.

“It’s not simply capitalist, though,” Coldicutt said. “It’s about power. It’s more about ego than it is about morals. Rather than doing a normal thing like paying taxes, a lot of entrepreneurs think, ‘Look, I can work out a better, more interesting way to do this.’ It’s very individualizing. There doesn’t seem to be much about community, much about civics.”

In San Francisco, this mindset flourished by the time the city supervisor Jane Kim took office in 2011. Kim, who represents the downtown district where most of the big tech companies have offices, began her tenure with the thankless task of negotiating a tax break for Twitter to keep the company headquartered in the city. The conversation had begun before she was sworn into office, and the then mayor, Ed Lee, was passionate about pursuing it.

“When I first got into office, my philosophy was the same [as today],” she said. “People should appreciate paying their taxes. It funds city services. It keeps the lights on, it pays for schools. But at the time, I knew I had to fix the past.

“At the beginning, it was rough,” Kim said. “A lot of folks in tech initially didn’t understand the role of government or care about the role of government. There wasn’t a general understanding that they were part of a larger community and everybody plays by a set of rules, including them. It wasn’t about hampering innovation, which was what I heard all the time.”

The stereotype of entitled yet unengaged techies emerged, with anecdotes of them “ruining” San Francisco and treating the city as their own personal playground persisting to this day.

But in the years since Kim’s intense introduction to tech world, she said, she’s seen many of the power players in the industry mature. They are now part of this city, as are their employees, and they now have a vested interest in making sure it thrives as well as their businesses.

“They realize they’re bigger players now and they have to play nice in the sandbox just like everyone else, and they have to be part of the community that their employees eat, live, work and play in,” Kim said.

This thinking goes beyond just industry leaders. Owski, the LinkedIn engineer rallying for Prop C, believes “there’s a growing movement of people within the tech industry who are starting to get more involved”.

“There are those within the tech industry who do care and are trying to do something about it,” he said.

Andrew, 32, an engineer for Synopsis who declined to give his last name, said one of the reasons he stood across from Owski that morning holding a sign reading “Tech Workers for Prop C” was because his time living in San Francisco had allowed him to experience one of its greatest challenges: the exorbitant rental market.

“An owner move-in eviction,” he said, describing a phenomenon wherein a landlord evicts a tenant so that they or a relative can move in. Tenant groups have argued that some landlords use this as a way to bypass rent control. “It happens to a lot of people. That helped me realize, since it affected me personally, that this would be so much harder for someone who has less resources to deal with these issues.”

Though Prop C may be the lightning rod, Pollock, of the League of Pissed-Off Voters, said he felt this trend toward civic engagement was an inevitable and natural progression that comes with living in a certain place for some time.

“These companies originally wanted to locate on the peninsula, but the workers wanted to live in San Francisco and the companies were forced to follow their workers up here,” he said. “Now the workers are sort of forcing San Francisco values on these companies, to some extent.”

And with talent retention an ever-present concern in Silicon Valley, tech leaders should focus on making sure their employees don’t have to avoid eye contact when they say where they work.

“At this point, you’ve got this real richness of brilliant workers in San Francisco who get to choose where they want to work,” said Jennifer Friedenbach, executive director of the Coalition on Homelessness, one of the architects of Prop C. “And they will want to work at places they will feel proud to work at.”