Force of nature: How the unstoppable Marc Benioff fueled Salesforce’s stratospheric rise

A handful of Salesforce executives are also milling about; they’re here for a meeting with Benioff too. One of them, the company’s chief design officer, is joining via videoconference. His floating face appears on a monitor that’s been wheeled out for the meeting. Every once in a while, he pipes up: “Is Marc there?” It’s not clear where the CEO is, or what he’s doing. But no one seems fazed by his absence. Thirty minutes go by. An hour passes. Where in the world is Benioff? The possibilities are endless: He could be texting with primatologist Jane Goodall. Or hobnobbing with his pal, actor Matthew McConaughey, who has said he’s “inspired” by the CEO’s leadership. Or maybe FaceTiming with Bono because, why not? Spend a little time with Benioff, and you quickly realize that these are all things that occur regularly in his realm. 

Few CEOs have achieved Benioff’s rock star–level status, complete with chronic tardiness and “world tours”—Salesforce-speak for the inexhaustible roster of global events the company puts on (and at which Benioff is usually the featured speaker). He has a prodigious social media following, including more than 1 million Twitter followers. He has written books and even become a magazine mogul, thanks to his 2018 purchase of Time, which he bought with Lynne Benioff, his wife of 15 years. He hosts the hottest lunch and the most sought-after party at “Davos,” the World Economic Forum’s elite winter shoulder-rub in the Swiss Alps. And he uses all of these platforms to evangelize not just his company’s products but also his laundry list of causes, from alleviating homelessness to saving the earth.

It would seem a matter of principle for the 6-foot-5 CEO: He doesn’t take on anything if it’s not big and bold. That is the driving management creed behind Salesforce, the company he cofounded in 1999 and has been running for 20 years, and which for the past decade has grown revenues faster than any other major software firm. Among the Fortune 500, just one other technology company—Facebook—has experienced a higher rate of sales growth from 2010 to 2020. (Salesforce clocked in at a 29.1% annual rate—a multi–g-force pace that bumped the company’s rank from No. 190 on last year’s Fortune 500 list to No. 137 this year.) And there don’t seem to be any brakes on this rocket—at least none that Benioff is inclined to press. Over the next five years, he proclaims to me and anyone else who will listen, Salesforce will more than double its revenue, from $21.3 billion to $50 billion.

Benioff is already nipping at the heels of his old employer, Oracle (ranked No. 80 on this year’s list), and he has his eye set on a far bigger rival—Microsoft (No. 15)—its fiercest competitor in enterprise apps like customer relationship management (CRM) software. “Salesforce is the only company that can challenge Microsoft in enterprise applications,” Anurag Rana, a senior analyst for Bloomberg Intelligence, tells Fortune.

The two companies will soon compete in another arena too: the contest for collaboration tools that allow distributed workforces to interact in real time—something that has grown even more essential since the start of the pandemic. Benioff sees that future and wants to seize it: “We want to be the leader in work from anywhere,” he says, as though the mere declaration were a five-year plan. 

But Benioff does have a road map: In December, Salesforce announced its planned acquisition of collaboration software maker Slack, a $27.7 billion deal that is expected to close this summer. Benioff wants Slack to be the future interface for his company’s tools. The colossal combo, which he’s referred to as a “perfect match,” is Salesforce’s biggest M&A move yet. Some analysts, though, are concerned the company overpaid for it. (The deal valued Slack at more than 30 times its revenue for fiscal 2021, its last reported year.) They are also worried that Slack, which struggled to grow at the same rate as some of its rivals during the pandemic, will ultimately dilute Salesforce’s margins at a time when they want the company to focus on profit, not revenue growth. “The Street gets very annoyed, because he’s constantly buying things, and he’s constantly going after [revenue] growth,” says Rana.

Now Benioff has to show that his riskiest purchase yet was worth the price tag—that Slack can become the central hub for all of Salesforce’s software, and that this integration can not only happen quickly but also give his products such an edge that it helps him get to his $50 billion goal. 

As onerous as that challenge sounds, it doesn’t appear to be enough for Benioff, who seems to yearn less for a top spot in the league tables than a place in the history books. In our conversations, few of the man’s sentences actually pertain to the products Salesforce sells—the stuff, for instance, that helps sales teams track their, um, sales. In their stead are sweeping proclamations about the steps he’s taking to fix the world’s biggest problems. He wants to cool and clean up the atmosphere by planting 1 trillion trees by 2030, a campaign he launched in early 2020 with his pal Goodall. He wants to clean up the oceans too. “I’m pivoting in my life,” Benioff tells me. “Today, a lot of my visions and meditations and thoughts are much more about climate change.” 

The CEO now allocates, by his own assessment, between 50% to 75% of his time on causes outside Salesforce—a data point that one has to wonder if Wall Street is paying attention to. His employees (some 60,000 of them), the media, and a growing community of fellow “activist CEOs” are also watching to see how he’ll pursue these grand philanthropic goals while running his company, integrating Slack, competing with Microsoft, and rewarding shareholders with at least the same 26% annualized total return they have been spoiled with since the stock went public in June 2004.

By the time Benioff does arrive at his house on the day of our scheduled interview—about an hour and a half late—such weighty questions have drifted from my mind. Dressed in a royal blue sports coat and dark slacks, he saunters into the room, his larger-than-life frame looming over the handful of people gathered around him. His longish hair, curling up at the base of his neck, is slicked back, and he’s smiling, energized, and voluble. He sits down at a large, circular table on his back patio, the expansive San Francisco Bay behind him, and holds court. “This is where Burning Man started,” he tells me, referring to the annual festival of art (and mind-altering substances) that now takes place in Nevada’s Black Rock Desert. He’s pointing to the resplendent beach behind him. And just like that, I’ve forgotten how far behind schedule he is. 

“You know, I think the genius of Stewart Butterfield is that he’s created an environment that lets anybody work on a phone or computer anywhere,” Benioff says of Slack’s founder and CEO, when our conversation finally does turn to the topic at hand. “And he’s done it in a much easier way. He’s a pioneer in this idea that this collaborative interface is what the future of computing is going to be.”

When Salesforce announced on Dec. 1 it had entered into an agreement to acquire Slack, many investors weren’t thrilled, says Mark Murphy, a research analyst with J.P. Morgan. “It’s a high multiple and high valuation for Slack. So it had better work because of that, or it’s going to be a big mistake.” By that day’s market close, Salesforce’s stock had tumbled more than 8%.

Benioff has acquired many companies over the years—more than 30 over just the past five years—a pattern that some have criticized as an effort to grow revenue at the expense of profit margins. But he says buying Slack offers a wholly different opportunity than previous purchases: to completely rethink how customers access and interact with Salesforce tools. 

More than a decade ago, Benioff tried to create his own collaborative interface, called Chatter. But the glorified group chat feature never really took off. “We kind of stopped innovating [on it], mostly because it wasn’t really a revenue item for us; it was more of an internal feed inside Salesforce,” says Benioff. 

5,076%

CUMULATIVE RETURN SINCE CLOSE OF FIRST TRADING DAY. SHAREHOLDERS OF SALESFORCE HAVE GOTTEN PLENTY SPOILED SINCE THE STOCK BEGAN TRADING ON JUNE 23, 2004, EARNING AN ANNUALIZED RETURN OF 26.3%.

Chatter may have been ahead of its time, or it may have been a subpar product because it wasn’t in Salesforce’s wheelhouse. Where the company does shine is in developing software that is designed for customer-facing corporate teams—think sales, marketing, and customer service. Salesforce’s first offering was targeted to salespeople: customer relationship management software, which sales teams use for tracking customer interactions, sending personalized messages, and all sorts of other things. (“CRM,” which is Salesforce’s stock ticker, represents about a quarter of the company’s revenue today, though it’s now the slowest-growing category.) 

But Murphy, the J.P. Morgan analyst, still says that Benioff has an uncanny ability to know where the puck is heading. “Salesforce is a company that understands the future of business,” he says. “It just stays ahead of the market at all times.”

Slack’s growth hasn’t been meteoric; nor has the company experienced the huge pandemic bump that some of its peers, like videoconferencing phenom Zoom, have seen. But the company’s product is sticky, especially for corporate customers with younger workforces. And in this case, the combination may well be worth more than the sum of its parts. “Salesforce is investing a lot in Slack,” Butterfield tells me in a recent interview. “I don’t mean money, I mean people. I mean like in the kind of platform integrations we’ve been trying to sell the world for a long time.” 

While Benioff has a flair for bombast, Butterfield has a reputation for nuance—and when we talk about the sale to Salesforce, he acknowledges that the gamble remains a big one: “Most M&A doesn’t work, so you kind of have to go into this believing that this is exceptional,” he says. Butterfield is quick to add that he believes this arrangement is exceptional. One of the reasons he’s optimistic, despite the odds being against the long-term success of the deal, is that he knows Benioff is throwing his full weight behind the plans for a deep integration of the two companies’ products. And if Benioff is on board, well, then it just might come to fruition. “He has demonstrated over and over again that when he really wants something to happen, it happens,” says Butterfield. 

There’s something else that unites the two founders, different as they are: a common enemy, Microsoft. Its Teams product, which it calls a “solution for work communications,” is bundled with its broader offerings of online enterprise tools, which helps give it a major boost when it comes to customer uptake. But the pandemic helped too: Microsoft says it now has 145 million daily users of Teams, up from 32 million at the onset of COVID. 

In the summer of 2020, Slack filed a complaint against Microsoft with the European Commission, alleging that the larger company was unfairly bundling its rival tool with its larger suite of widely used products. (Microsoft vigorously denies the claim.) Salesforce has had its own beef with Microsoft too. Back in 2015, Microsoft tried to buy Salesforce, but talks reportedly fell apart. And the two companies have sold competing products for years, though Salesforce is well ahead when it comes to its signature product, CRM, which has more than four times the market share of Microsoft.

Butterfield himself presents another potential asset to Salesforce and its ability to compete in the future. Like Benioff, he’s a visionary, though he represents a different generation: one that’s more proficient with emoji.

Another asset, insiders say, has been Bret Taylor, now Salesforce’s president and chief operating officer, who came into the company via the 2016 acquisition of his startup, Quip. Taylor, who is also a former chief technology officer at Facebook, is considered by many to be Benioff’s heir apparent. “Marc’s shoes are impossible to fill,” says Taylor. “Whoever comes after Marc will have to make their own imprint on the company.”

Salesforce is investing a lot in Slack. I don’t mean money, I mean people. I mean like in the kind of platform integrations we’ve been trying to sell the world for a long time.

Stewart Butterfield, cofounder and CEO, Slack

Benioff has said that it was Taylor and Butterfield who initially approached him with the idea for the Slack deal. And the two men could represent a new era at Salesforce—that is, if they stick around. Salesforce has a mixed record when it comes to holding on to the founders of companies it acquires, and, sometimes, to its executives. In 2018, Benioff promoted his then-COO, Keith Block, to become his co-CEO. But the dual CEO arrangement did not last long. Block left the company in February 2020, after less than two years in the position. And Benioff resumed the role of sole CEO. (At the time of Block’s departure, Benioff expressed his gratitude for the exec’s service, saying, “Keith’s strategic thinking and operational excellence have deeply strengthened our company, and our close friendship endures.”)

“When he left, initially a lot of us on Wall Street thought that could be a big problem,” says Rana, the Bloomberg Intelligence analyst. But investors soon saw that it didn’t impact the company’s ability to keep up with its rapid growth—as long as Benioff was still running the show. “And trust me,” says J.P. Morgan’s Murphy, “he runs the company.”

That last part is the clincher: Salesforce, to many investors, is Benioff. As Murphy says, “Marc can’t live separately from Salesforce. This is his identity.”

The question for shareholders, customers, and his largely enthralled mass of employees is, What if that wasn’t the case?

Benioff wasn’t always the boss, though he clearly aspired to be from early on. He cut his teeth at Oracle, the database and applications provider, under the wings of its notoriously brash founder and former CEO, Larry Ellison. “I was the youngest vice president of a company when I was like 26, and I didn’t have any leadership training,” says Benioff. 

He wasn’t just inexperienced, he also had a problem focusing his attention, as he tells it. There were a million things he wanted to do, and spending the rest of his career working for another alpha male wasn’t one of them. Besides, he saw huge opportunity in an emerging business model: selling enterprise software over the web. The consumer Internet had already taken off, but companies weren’t yet conducting their business operations online. So, in 1999, Benioff left Oracle and started Salesforce. The idea? Instead of clunky, pricey software that companies bought for millions of dollars and then had to spend even more customizing it for their needs, Salesforce would develop tools that could be accessed online, and bought as a subscription. Customers wouldn’t have to invest in infrastructure to host the computing power these applications required; Salesforce would take care of all of that for them, in the cloud. 

Selling subscription-based software over the web doesn’t sound all that revolutionary today. But in 2004, when Benioff took Salesforce public, nobody on Wall Street really understood what he was doing. 

“Here you have this company coming public with this larger-than-life guy bragging about how software-as-a-service was the next big thing,” says Peter Goldmacher, a former analyst who now serves as head of investor relations for another, younger, cloud-based software company, New Relic. “It was pretty close to the early 2000s [when the dotcom bubble burst], and nobody was in the mood.”

Goldmacher was the first sell-side analyst to start covering Salesforce. “I knew everyone at the company because it was the Oracle all-star team,” he says. “I didn’t have any insights into the cloud or SaaS, but these guys can sell ice to Eskimos, and that’s all I needed to know.”

Goldmacher was right. Benioff had brought a handful of the best salespeople from his previous employer along for the ride. Together, they not only pioneered a new product category, they also changed the way software is sold and valued by Wall Street. It was a bumpy start, just getting investors to understand this new business model. But if anyone could convert the naysayers, it was Benioff. 

“That’s where his persona, and quite frankly his physical persona, came in,” says Dominic Paschel, another longtime software insider who worked on Salesforce’s investor relations team from 2004 to 2008. Paschel remembers how Benioff captivated investors when he was on the road, even if he didn’t—or maybe because he didn’t—stay on the talking points his team had prepared for him.

Nearly every chance to talk with investors, analysts, the media, or his own sales team became another opportunity for showmanship. “He just kept living larger and larger,” says Goldmacher, who recalls seeing musician Neil Young onstage at a Salesforce analyst day in the company’s early days. “What the fuck does Neil Young know about software?” wondered Goldmacher at the time. “But he was Benioff’s friend, so why not?”

Those who know Benioff well, though, say that the sizzle and spectacle are there to serve more important ends. “Marc is a rare combination of showmanship and substance,” says Julie Sweet, CEO of Accenture, who has partnered with Benioff on several projects over the years. “Those two often don’t come together. But Marc has a lot of credibility because he actually does what he’s passionate about.”

That’s particularly true when it comes to his commitment to social and environmental causes. “He wrote the book on stakeholder capitalism,” says Klaus Schwab, the founder and executive chairman of the World Economic Forum, referring, quite literally, to not one but several books Benioff has written on the subject. 

Michael Dell, CEO of the $94 billion-in-revenue Dell Technologies (No. 28 on the Fortune 500) has known Benioff for decades and calls him his “brother from another mother.” Dell can remember the Salesforce founder championing progressive causes early on, going back to his days as a young executive at Oracle. “He deeply believes that business is the greatest force for change in the world,” says Dell. “And his actions back it up.”

All of this—the showmanship, the championing of stakeholder capitalism, and yes, selling good, old-fashioned enterprise software to companies great and small—fold together in a single annual event: Salesforce’s Dreamforce conference, the enormous star-sprinkled celebration/trade show/retreat that Salesforce throws every year, and which shuts down San Francisco for days.

Dreamforce is where the software company CEO meets Benioff the tireless impresario and Benioff the true believer. Onstage, in front of legions of company faithful—the sales reps, programmers, and others whom Benioff calls “Trailblazers”—the salesman-in-chief doesn’t hawk his company’s enterprise software; rather, he sells inspiration, a sense of belonging, celebration, mission. At Dreamforce 2018, he motivated his flock to take “personal action to change the world.” At Dreamforce 2019, he said excitedly that it wasn’t strings of computer programming they were offering customers, but rather an “intelligence revolution.” At Dreamforce 2020, delivering his remarks outside (and minus the adoring crowd) owing to the pandemic, he reminded his team that business was “the greatest platform for change.”

Even those who don’t love the showman’s shtick agree that Benioff has a track record of putting his money and his actions where his mouth is. When he launched Salesforce in 1999, he created the Salesforce Foundation, a philanthropic arm of the company, and developed what he calls a “1-1-1” model: The company committed to put 1% of its equity into its foundation when it was founded, and each year allocates 1% of its employees’ time to volunteer work, and donates 1% of its product to nonprofits. Benioff’s muse for this benevolent approach to business was an unlikely one: former Secretary of State and four-star general Colin Powell, who has sat on Salesforce’s board since 2014.

“What the f–k does Neil Young know about software?” marvels one tech industry veteran after seeing the musician at a Salesforce event for Wall Street analysts. “But he was Benioff’s friend, so why not?”

Peter Goldmacher, head of investor relations, New Relic

In 1997, when Benioff was still at Oracle, he heard Powell give a speech in which he urged business leaders to use their privilege, platform, and resources to do good in the world. 

Benioff and Powell were eventually introduced, and the former cabinet official smartly enlisted Benioff’s help to procure computers for a struggling high school in D.C. “Lo and behold, you don’t have to ask Marc that twice,” says Powell, who recalls Benioff showing up on the site shortly afterward with a truckload of laptops.

Of course, in the philanthropic ethos of Benioff, there is no virtue in keeping such good deeds to oneself. “I don’t know how many times he’s told that story [about the laptops],” says Powell, laughing genially. “Marc has never stopped talking about it.” But the repetition helps reinforce the world-changing lore. For Benioff, as with any great salesman after all, it only counts if you sell it.

Sixty-one stories high, Salesforce Tower is the tallest building in San Francisco, hanging over the city’s skyline almost comically. On this day in mid-March, I’m on the top story, the “Ohana” floor—a name that translates to “family” in Hawaiian and that seems to mean a full menu of wholesome virtues in Benioff-speak. Ohana is a kind of spiritual destiny for all things Salesforce, and Benioff, who has a home in Hawaii, weaves the term (and other Hawaiian words) into everyday conversation and even into his letters to shareholders.

Today, Benioff is leading one of Salesforce’s weekly all-hands, which the company started doing when the pandemic hit a year earlier. The Salesforce Tower is still technically closed, but Benioff and his chief business officer, Ryan Aytay, are on hand to direct their massive Zoom call, livestreamed to thousands of employees, from the plushiest and most scenic of Salesforce’s new digs, which finally reopened to vaccinated employees in mid-May.

I’ve been allowed to observe the all-hands. But I haven’t been given a heads-up on what it’s going to be about. Unsurprisingly, the topic at hand doesn’t have much to do with enterprise software. And, just as on-brand, Benioff has a surprise celebrity guest. San Francisco Mayor London Breed appears—in person. Breed, who is the first Black female mayor in the city’s history (and to whose campaign Benioff donated generously), is there to help the CEO talk to his employee base about a difficult topic: allegations, made by a couple of recently departed Salesforce employees, that the company’s culture is toxic for Black women.

Benioff has prided himself on being both a socially conscious CEO and an activist one. He canceled company events in Indiana after it passed what many consider to be a law that discriminates against transgender people. He has personally and aggressively lobbied for a bill in San Francisco that aims to raise corporate tax dollars to provide housing and services for the homeless.

But all that wokeness wasn’t enough last spring, when George Floyd was murdered at the hands of a white police officer in Minneapolis. The social unrest that ensued focused on police brutality, but also on corporations’ role in the struggle for racial, ethnic, and gender equality. Suddenly, even the Bay Area’s most liberal leaders felt pressure from many employees to do more—to not just work “toward” better representation and inclusivity in their workforces, but rather to show that they were achieving both.

Over the past few months, two of Salesforce’s Black, female executives left the company and suggested that Salesforce, despite its high-minded talk, was no better than the rest. Each executive publicly shared their resignation letters, which included several complaints about Salesforce’s culture. The first complaint came from Cynthia Perry, a former senior manager of design research, who, in an open letter on LinkedIn, said she had been “gaslit, manipulated, bullied, neglected, and mostly unsupported” by a person whose name she redacted from her public post. “It’s not a place of opportunity,” wrote Perry. “It’s not a place of Equality for All.” 

Vivianne Castillo, a former manager of design research and innovation at the company, in a letter she published several weeks later, echoed some of the same allegations Perry had made. Castillo also added specific examples of how she’d been made to feel like she had to take on additional, unpaid work in order to help Salesforce with its diversity initiatives—something that wasn’t part of her job description. And she called out Benioff’s culture—even his “appropriation” of Hawaiian words—as empty promises, devoid of real action.

Benioff says he was caught completely off guard, and quickly set up an all-hands call to discuss the criticisms. In the conversation with Mayor Breed, Benioff shared his concerns that he, like so many other leaders, had blind spots when it came to race and gender. “Give us some coaching,” Benioff asked. “What are some things that we could do to improve the Black, female experience?”

Breed provided a few tried-and-true suggestions, such as workshops and bias training—and then offered something more profound: “I think part of what’s important for us to do as people is to just think about what we’re saying before we say it.”

Ebony Beckwith, CEO of Salesforce’s foundation and the company’s chief philanthropy officer, was another “guest” speaker on that day’s all-hands, though she appeared over Zoom. (She, too, is a Black woman.) “Marc was asking me, ‘Why is this all coming up right now?’ ” Beckwith told me in an interview that took place after the company meeting. “It’s because we’re at a point in life that it’s okay to be talking about this in corporate America. What used to be a taboo subject is everywhere now. And it highlighted some things we needed to work on internally as well.”

According to Beckwith, Salesforce has taken several actions since the allegations by Perry and Castillo surfaced, including training for employees to better understand what microaggressions look and feel like. “No one was talking about this stuff [pre-George Floyd],” says Beckwith. “I don’t know if I would have felt safe, as a Black woman, talking about this either.”

As for Benioff, he tells me he sees the experience as an opportunity. It’s another chance for him to work on the company culture and make it a model for others. Since the allegations from Perry and Castillo surfaced, in fact, the CEO has asked his team to update their strategy and plans for equality at Salesforce. “We’re not perfect,” says Benioff. “But we’re willing to look at ourselves.”

That introspection has only grown in intensity in recent years. Benioff, now 56, is deeply pondering the next phase of his life. “I look at life in four quadrants, and I’m kind of moving into quadrant four,” he tells me during our conversation on his patio in early spring. 

Some have speculated that Benioff would run for some sort of political office someday, in his post-Salesforce future. But the CEO says he has zero intention to do so. “I’m much more of a creative person,” he says. “I don’t have a political personality. Like, in my meditations or in my conversations, it has never ever come up.”

The challenge that calls most strongly to him now is climate change. “The No. 1 issue in the ocean is acidification,” he says, pointing to the bay behind him. Then he rattles off statistics—how many gigatons of carbons we’ve emitted since the first Industrial Revolution, how we’ve deforested 3 trillion trees, and other depressing facts. 

This is the scale of challenge Benioff wants to focus on in his so-called fourth quadrant. He also wants to be a guide to other business leaders. He mentors younger entrepreneurs and says CEOs regularly call him up for advice. And for all of his do-good projects, you can bet he’s bringing in some star power.

“Sometimes Marc will text me and on that thread is Matthew McConaughey and Chris Rock,” says musician Will.i.am. “There’s one thread with me and LL Cool J and Willie Nelson and Willie Nelson’s son. It’s a beautiful mix of different worlds, and Marc sees the beauty of having these worlds connected.”

For a CEO who lives his life onstage, it seems fitting. “I never thought in a million years that this is where we would be,” Benioff tells me, referring to the massive growth of his company. It’s a good sound bite—the man knows how to think in headlines—but somehow, I doubt it’s true. 

Benioff’s biggest bets

The Salesforce CEO has made 30-plus acquisitions in just five years. Here are his priciest purchases to date.

Slack 

Price: $27.7 billion
December 2020 
(deal announced)

Benioff says Slack will become the “central hub” for all of Salesforce’s applications. The deal, Benioff’s biggest acquisition yet, is expected to close this summer. 

Tableau 

Price: $15.7 billion 
June 2019

The popular analytics platform was snapped up by Salesforce just two years ago. But its CEO, Adam Selipsky, is now heading back to his former employer, Amazon.

Mulesoft 

Price: $6.5 billion 
March 2018

MuleSoft helps customers integrate data from a variety of applications. That includes Salesforce-made software and tools made by other vendors.

Demandware

Price: $2.8 billion 
June 2016

This acquisition filled a gap in Salesforce’s suite of products, jump-starting its “commerce cloud,” which offers customers e-commerce tools, in addition to its other enterprise apps. 

This article appears in the June/July 2021 issue of Fortune with the headline, “Force of nature.”