And then he wrote checks, with lots of zeroes, to San Francisco schools and later to Oakland schools, money from his company's foundation and then from Salesforce directly for iPads and Internet access. Then he added support for coding classes, math coaches, pushing computer science into classrooms, setting up maker labs and more.
Last year, according to Salesforce chief impact officer and executive vice president Suzanne DiBianca, they asked the same questions and added one more: "How are you thinking about AI?"
And the response was "we're not," she said.
On Monday, Benioff, through his company, pulled out his checkbook for the 12th time for Bay Area schools, this time adding resources to incorporate artificial intelligence in the educational process.
San Francisco and Oakland were among the biggest recipients, with grants totaling $10 million to pay for a range of programs and resources, part of $23 million in funding from Salesforce for schools and education nonprofits across the country this year.
Since Benioff's first donation to San Francisco Unified in 2013, his company has given $150 million to U.S. schools.
"Our north star is the public schools," DiBianca said. "There's nothing more important than public education."
The inclusion of AI in Salesforce philanthropy started last year, including the launch of an AI Accelerator that supports nonprofits creating AI-powered tools and technology, including many directed at education.
"What is happening in the world is this massive swell of AI technologies that are entering the classrooms, whether they like it or not," DiBianca said. "We're really trying to help the districts navigate that."
That includes offering access to artificial intelligence in the form of "agents," she said, platforms that can help perform a range of tasks, including guiding students through the early college application process. That means the college counselor at a high school, with a large load of students, can focus on specific needs rather than spending time on basic information such as the different types of universities and what might be a good fit.
Another platform can help students write a resume and do mock interviews to get ready for a job or to tutor students in coursework, allowing educators to dedicate more time to specific needs.
"It's moving pretty quickly," DiBianca said. "It enables (teachers or counselors) to serve more students, in a deeper way and a much more time-efficient way."
At Washington High School in San Francisco, teacher Carrie Karlovic sees a huge need to expose students to AI.
"We definitely have conversations about how to use it," she said. "I'm not somebody who thinks you can put the toothpaste back in the tube."
In her classes — Advanced Placement Language and Composition, and Film as Literature — artificial intelligence is often a topic that is included in the curriculum, even if it's not used as a tool in class, she said.
"AI is us just on a computer scale," she said she tells her students, "where all of the biases and prejudices get absorbed."
At Salesforce, DiBianca said it's important that students get equal access to the evolving technology.
"We don't want to create a new digital divide with AI," she said.
San Francisco officials applauded the company's long-term spending on city schools.
"Emerging technologies like AI will continue to impact our schools, workplaces, and society," said San Francisco Mayor London Breed in a statement, describing the city as the AI capital of the world. "I'm grateful for Salesforce's pursuit of equality through technology access and helping students and teachers be prepared for the AI future."
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