At Fortune’s Brainstorm Tech conference last week, the 35-year-old entrepreneur shared that instead of turning to executive coaches for wisdom, he prefers candid one-on-one conversations with fellow entrepreneurs.
“I try to kind of go and call people up for an hour at a time,” he told Fortune Editor-in-Chief Alyson Shontell on-stage during a live recording of the Fortune 500: Titans and Disruptors of Industry podcast. “If I can just get their advice on AI or marketing or sales, learn just a little bit, ask them who they’ve learned a lot from in particular fields and just kind of jump from person to person, that’s been very helpful.”
Founded in 2019, Ramp now boasts a $22.5 billion valuation thanks to multiple funding rounds this summer, plus a roster of over 45,000 customers. Under its hyperspeed strategy, Ramp accounts for about 1.5% of the $2 trillion corporate and small-business credit card market in the United States, as Fortune’s Leo Schwartz reported in the latest magazine issue.
Key mentors
Two leaders in particular, Glyman said, have served as trusted guides for his six-year-old company: Fidji Simo, the French tech executive who now runs OpenAI’s consumer applications business, and Satya Nadella, Microsoft’s longtime chief executive.
Offstage, Glyman credited Simo as an “incredible entrepreneur,” noting her stewardship of Instacart’s long-awaited IPO in 2023, and praising her new role as the first-ever CEO of Applications at OpenAI, reporting directly to Sam Altman.
“I just think that her ability to go and get the best out of people, to understand people’s capabilities, to teach them and understand what are their spikes and help make their spikes sharper—I think that’s extraordinary,” Glyman said, adding that he believes Simo is “very underrated.”
In 2023, Ramp announced Simo as an individual investor and advisor, along with other AI leaders including Microsoft CEO Satya Nadella, Quora CEO Adam D’Angelo, and Stanford AI Lab professor Chris Re.
“They truly earned every bit of their success through profound customer obsession,” Simo later shared in a 2024 post on X marking Ramp’s anniversary.
Glyman described Nadella as an “exceptional leader,” praising both his Wall Street successes and his management style during his decade at the helm of Microsoft.
“Not only has he created something like a billion dollars in market cap for every day that he’s been in the seat, but I think what’s more interesting about him is he is an avid listener,” Glyman said. “He’s a reader. He’s deeply curious. He wants to ask why.”
The fintech founder pointed to Nadella’s track record for placing prescient bets on AI’s potential, including a $10 billion investment in ChatGPT creator OpenAI in 2023, plus key hires in a highly competitive talent war, including Google DeepMind cofounder Mustafa Suleyman.
“[Nadella] was really the first major CEO to see the potential of what AI and large language models could do,” Glyman said. “It was because he was less busy talking and giving advice. He was more busy asking questions, being curious and reading.”
Big bets pay off
The big gambles on AI are paying off. In July, Microsoft briefly topped $4 trillion in market capitalization after a blockbuster quarterly earnings report, joining Nvidia as just one of two companies to reach the milestone. However, the tech giant has also simultaneously undergone a significant internal transformation, axing more than 15,000 positions—about 7% of the company’s global workforce—since January, making its largest personnel reduction since 2014.
Nadella addressed the cuts in a memo to employees, citing “uncertainty and seeming incongruence” for the staffing reduction while also noting a “thriving” market performance and AI investment.
“Years from now, when you look back at your time here, I hope you’ll say: ‘That’s when I learned the most. That’s when I made my biggest impact. That’s when I was part of something transformational,’” Nadella wrote.
Glyman credits more than just innovation for Microsoft’s staying power as one of the world’s most valuable tech companies; he points to Nadella’s servant leadership as a cornerstone of the tech giant’s enduring success.
“I think what’s so special about him is, he’s not just going and trying to impart wisdom,” Glyman said. “He actually is just as curious and wants to learn, and I think through the questions he asked, I’ve learned so much from him.”
Ramp’s hiring philosophy
Glyman’s leadership lessons have translated into key hiring strategies as his startup continues to scale at speed. He points to Nadella’s growth mindset and culture of “learn-it-alls” as evidence for Microsoft’s corporate wins.
“He’s focused on demanding and expecting the most from people at Microsoft, but also making clear that everyone at the organization matters,” Glyman said. “Every person has a part to play, and everyone has the chance to transform the company.”
It’s a blueprint Glyman channels into Ramp’s own hiring playbook as the fintech startup aims to capitalize on newly launched AI-powered autonomous finance agents to compete with finance giants like American Express and Chase.
“I try to look for great operators, people who are not going to drop the ball, people who are better at sales, better at pieces of marketing, better at engineering,” he said. “I actually think it’s a joy to kind of go and find people who can teach you things.”
While Glyman joked on stage that Ramp’s “hot yellow” branding and splashy advertisements may be why his startup is attracting top talent in an increasingly competitive AI arms race, he insists the real driver is the opportunity for impact at scale.
“If you can go and build a strong team, try to empower people to double down on what makes them great, not try to go and fix their deficiencies, that’ll help you have a much more well-rounded company.”
