In 2014, newly single Stanford MBA candidate Amanda Bradford was fed up with the “hot or not” game she was playing on dating apps. Unimpressed with her matches and emboldened by the Silicon Valley start-up scene, she founded The League: An exclusive dating app geared at high-earning, high-achieving professionals with high standards.
The idea resonated, skyrocketing Bradford’s company; in 2022, she sold it to the Match Group (which owns Tinder and Hinge) for a reported $30 million. (Bradford and her team netted over $10 million from that sale, per Fortune’s calculations.) Deeply committed to the brand identity, she’s still the app’s CEO, and likely wouldn’t have launched it without inspiration from her first boss: Salesforce’s Marc Benioff.
“My first job after college was working for Salesforce,” Bradford told Fortune in an interview—first as a sales engineer and later as an account executive. Bradford arrived at Salesforce, per her LinkedIn page, in May 2007. That was “the era of the cloud, where everything was going to the cloud,” she said. “And Salesforce was the pioneer.”
Because she onboarded during the company’s first decade—it was then still called Salesforce.com—Bradford “got front row seats to the whole software as a service industry.” She also got exposure to Benioff, who she said was “an amazing CEO.”
“I learned a lot just watching how he operates his business,” she said. “And from there decided that I wanted to stay in technology and keep growing as an entrepreneur.”
Learning by example
Like Benioff, who built Salesforce from the ground up and has led the company ever since, Bradford began work on her app all on her own. “I built and designed The League for myself as a user,” she explained. “I did do some focus groups, but for the most part, the focus group was me, and I built the features that I wanted.”
She also relies on the coding skills she honed as a computer science major at Carnegie Mellon—and put into action at Salesforce. “Every time I come up with a new idea, or someone gives me a great idea, I can actually ship it and build it into the app and have people use it within a month or two—sometimes even weeks at this point,” she said. “I love the ability to build, to iterate, and to be responsive to what’s going on in the environment.”
And she’s far from the only executive Benioff has influenced.
“Marc has been a towering exemplar of what it means to be an innovative and forward-thinking leader,” Ken Frazier, former CEO of Merck, said when Chief Executive Magazine honored Benioff as its 2022 CEO of the Year. Fortune has named him one of the World’s 25 Greatest Leaders, and Harvard Business Review included him on its list of the 10 Best-Performing CEOs.
Benioff’s much-lauded leadership style focuses on belonging, equality, and inclusion. He often refers to the “Salesforce Ohana,” an ethos that emphasizes Salesforce’s we’re-a-family mentality—unusual for a Silicon Valley giant, much less for a company leading the world in customer relationship management (CRM). He also, since Salesforce’s 1999 founding, has committed 1% of its equity to philanthropic causes, especially in diversity and access in the tech and AI fields.
But sometimes the “aloha” approach can run counter to Benioff’s actions. Last year, the software firm announced a 10% workforce cut, news Benioff broke to employees in an email dotted with “Ohana” references and reminders that coworkers are family. In an all-hands call a day later, Benioff reportedly dodged questions about the layoffs, frustrating remaining workers.
“Given how little of this call has addressed the layoffs, the questions asked in this channel, and the ‘family’ who were laid off, should we consider retiring the phrase ‘Ohana?’” one employee wrote in an internal Slack channel at the time, per an Insider report.
Still, though, it’s clear that Benioff has left a positive impact on some of his former workers like Bradford. Once she scaled The League enough to hit the million-dollar mark for her own personal wealth, she didn’t shell out on anything flashy. “I helped my parents put a down payment in for a retirement community that they were excited about,” she said.
Perhaps she was guided by a Hawaiian word for family—one that means no one gets left behind.