Microsoft Chief Executive Officer Satya Nadella Saumya Khandelwal | Reuters

Microsoft is one of Wall Street's most obvious turnaround stories in recent history. The company has added almost $500 billion to its market cap since Satya Nadella took the CEO position five years ago today. Internally and externally, the company is viewed more favorably than it was under Nadella's predecessors. But Nadella has not yet joined the ranks of the world's most valuable individuals. Meanwhile, Microsoft co-founder and original CEO Bill Gates is the second-richest person on the planet, with a net worth of $95.7 billion, and the company's second CEO, Steve Ballmer, is worth approximately $39.2 billion, according to data from Bloomberg.

However, executives typically don't reach billionaire status with a resume like Nadella's. Typically, they'd have to found the company, like billionaires Marc Benioff of Salesforce or Mark Zuckerberg of Facebook. Or they'd have to be CEO of the company for several years, like JPMorgan Chase CEO Jamie Dimon, who has been CEO of that company since 2005. Dimon became a billionaire in 2015, according to Bloomberg. In the most recent fiscal year, which ended on June 30, Nadella received $25.8 million in total compensation, according to Microsoft's most recent proxy statement. That's up 29 percent year over year. His pay was higher than many other CEOs of companies in the S&P 500. But it's lower than the chiefs of companies with lower stock growth over the past five years, like Oracle's Mark Hurd ($108.3 million), Walt Disney's Bob Iger ($65.6 million) and 21st Century Fox's Rupert Murdoch ($50.3 million). Taking into account a recent stock sale and his Microsoft holdings, Nadella is likely worth more than $320 million. But not much more. "Whatever they're paying him, it's not enough," former Microsoft executive Brad Silverberg told CNBC. Nadella once worked for Silverberg, who left the company in 1999 and is a founding partner at venture capital firm Ignition Partners. He provided input for the selection of Ballmer's replacement. Silverberg took into consideration the qualities he remembered about Nadella — that he was humble, and that he recommended strategies that were in the best interest of the company, not himself. He thought Nadella, then a 22-year company veteran, would make a great CEO, and today he feels Nadella exceeded his expectations. "I'm really happy with his contributions to the company," Silverberg said. "Obviously the stock price is one metric, but if you look at the internal culture of the company, people are happy there. People are really proud to work for Microsoft. I think he's done a lot to make that happen."

Investors are happy with Nadella as well: Microsoft's stock has risen nearly 182 percent since Nadella took over, according to FactSet. "If you look at the stock's more than doubling in value, clearly one could argue he's underpaid relative to the wealth creation he's been able to do in the stock," said Brent Bracelin, managing director at KeyBanc Capital Markets. "They have been able to transform one of the legacy client-server models, and they're now becoming the leader in cloud across IaaS [infrastructure as a service] and SaaS [software as a service], and he's done it, yet, look at his comp." Microsoft's perception has improved in Silicon Valley, too.