UPDATE: Salesforce co-CEO Bret Taylor steps down after only one year in the role

Everyone in Silicon Valley seems to know Bret Taylor.

Few outside do.

That’s going to change, as the software engineer turned corporate dealmaker assumes a growing role at Salesforce, a tech company whose marketing and sales tools have only become more vital during the pandemic.

Salesforce’s $27.7 billion acquisition of Slack this month has thrust Taylor, the acknowledged architect of the deal and the company’s chief operating officer, into the spotlight. It has also renewed talk of who might one day succeed co-founder Marc Benioff, 56, as CEO of the San Francisco company. There is little discussion of anyone but Taylor.

Taylor, who turned 40 in July, built his resume at Google and Facebook. He’s on the board of Twitter. And he’s won the respect of entrepreneurs and investors by starting two companies, a badge of honor in a startup-obsessed industry.

He’s also a clear product of the Bay Area — an engineer and a marketer raised by an engineer and a marketer, a public high school graduate who went on to Stanford like his father. Taylor, who grew up in Lafayette and lives there with his wife and three children, calls himself an “East Bay loyalist.” There’s no moving to Austin or Miami for him. Even as he creates and buys tools that make remote work easier, he’s talking about post-pandemic plans to get thousands of Salesforce employees “back to the Tower.”

It’s just one of the many challenges he faces as Benioff’s right-hand person, along with making the Slack deal pay, beating back competition from the likes of Google and Microsoft and communicating a less-mystifying version of what Salesforce does. He also needs to sell big, lumbering businesses a vision of the future of work that looks a lot like the tech giants and startups he’s toiled at over the past decade and a half.

People who have known Taylor for years think he’s up for the task. Frankly, they’re not even sure he’s capable of failing.

“Bret can’t help but do a good job,” said Paul Buchheit, a partner at the Y Combinator startup incubator. The two of them co-founded FriendFeed, a social networking site, 13 years ago and sold it to Facebook a couple of years later. Buchheit worked on a few projects at the social network and left. Taylor, because of his work ethic and general brilliance, rose up to be a key adviser to Facebook CEO Mark Zuckerberg.

Taylor, after leaving Facebook, founding Quip, a maker of online document-collaboration software, and selling it to Salesforce in 2016, is once again at the side of a famous founder. But this time, it seems like he might stick around. He’s not just Benioff’s No. 2; he’s a name whose very mention makes Benioff light up.

“So Bret, do you want to take this to another level?”

That’s how Benioff tossed the virtual mike to Taylor on a call with Wall Street analysts to discuss Salesforce’s quarterly earnings. The words could also describe the challenge Benioff put in front of Taylor a year ago, when he promoted him and put him in charge of what is now the largest group within Salesforce’s 54,000 employees.

Benioff handed over functions that he had long guarded for himself, like marketing, product and engineering. Soon analysts, trade publications, even the Economist were talking about Taylor as Benioff’s heir apparent.

Taylor’s promotion was swiftly followed by the unexpected and still somewhat puzzling departure of Keith Block, a software sales veteran who had the title of co-CEO, in February. I asked Benioff if Taylor was filling a hole Block left. Benioff’s answer surprised me: Taylor, he said, was really replacing George Hu.

If Taylor is obscure outside tech circles, Hu is even more so. But the tech executive, who is now chief operating officer at Twilio, another cloud software company, is legendary within Salesforce for rising from an intern and getting personally mentored by Benioff. Before leaving in 2015 to found a startup, Hu rose to chief operating officer. Along the way he revamped Salesforce’s marketing, fixed the company’s European operations, and developed new small-business products.

By comparing him to Hu, Benioff is saying he sees in Taylor a jack-of-all-trades executive who can rapidly absorb information and come up with insights others can’t. He is also suggesting Taylor is a beloved protege who can be trusted with imposing tasks. It doesn’t matter that Taylor hasn’t done a $28 billion software acquisition before: How many people can say they have? Who says he can’t?

Bret Steven Taylor was born in 1980 at the Kaiser hospital in Oakland — an entry point he shares with Kamala Harris, the vice president-elect, he notes. (He donated to Joe Biden’s presidential campaign, records show.)

He grew up in the East Bay, save for a middle school stint in Georgia, where his mother’s work temporarily took the family. His father, Steven, started a heating and ventilation engineering firm in Alameda that has done work for the Oakland Cathedral, Gap headquarters and Pixar’s Emeryville offices. His mother, Sheila, worked as a vice president of marketing at Chevron before starting a Wine Country tour business.

Taylor graduated from Acalanes High in Lafayette in 1998. It wasn’t always challenging. “I can afford to miss a couple days of school and make it up pretty easily,” he told The Chronicle as a senior, so he could go on a family trip to Hawaii. Though the Taylors were well-off enough to afford trips to the islands and Lake Tahoe, he got a summer job at a 76 gas station. After some time pumping gas and scrubbing toilets, he started designing websites for neighboring businesses, which was far more lucrative.

“He credits cleaning out bathrooms for his success in life,” said Casey Muller, a friend who was also an early employee at FriendFeed.

He followed his father to Stanford, though he initially thought he would study to be a lawyer. According to the Stanford Engineering website, an elective course in computer science taught by lecturer Jerry Cain changed his mind, and he ended up getting a bachelor’s in 2002 and master’s in 2003 in the field.

Marissa Mayer, the early Google employee who went on to run Yahoo, had started recruiting talented individuals who might mesh with the search startup’s quirky, engineering-driven culture; they were dubbed associate product managers. Business Insider called the APM program “the closest thing Silicon Valley has to Professor X’s School for Gifted Youngsters.”

Taylor, one of the earliest associate product managers, lived up to those expectations, helping build Google Maps on top of a startup the company had acquired. He was the product manager, not an engineer, but that didn’t stop him from coding. The early Maps was too slow.

“He got frustrated and one weekend rewrote” the underlying code, said Buchheit, making it “one-third the size and 10 times as fast.” That made an impression on Buchheit, who was using similar technology on Gmail, the product he’s famous for. Taylor’s programming skills even drew notice from Google co-founders Larry Page and Sergey Brin.

Taylor also caught the attention of another associate product manager, Karen Padham. The two married in Douglas County, Nev., in 2006. She continued to work at Google through 2010; her name is on 13 patents, most involving online advertising and video technology.

Mayer expected that graduates of her program would turn out to be entrepreneurs. Indeed, Taylor left Google in 2007 along with a Stanford classmate, Jim Norris, to pursue a startup.

Benchmark, the venture capital firm, hosted him and Norris as entrepreneurs in residence, a cushy position where promising would-be startup founders get paid to cook up ideas in exchange for giving the investors an early look. Buchheit and another ex-Googler, Sanjeev Singh, were also knocking around startup ideas, as well as former colleagues they could team up with. The four joined forces on an idea that became FriendFeed.

Taylor wanted to move quickly. Ana Yang, an ex-Googler, was traveling in China when she messaged Taylor about his new startup. “When can you start? How about tomorrow?” she recalled him replying. She returned to California to find a pile of paperwork to incorporate the company. Her title was chief miscellaneous officer.

FriendFeed, whose software let people share links and consolidate updates from multiple social networks, had a cult following in tech circles. In a hangar-like office in Mountain View — real estate was cheap following the dot-com bust, and the building was slated to get torn down — Buchheit, Taylor and a small group built features that would soon become standard in social networking, such as comments on updates and a “Like” button. A private networking feature called Rooms would presage both Facebook Groups and workplace chat tools like, well, Slack.

But FriendFeed was struggling, and Facebook swooped in.

“Our growth had basically flatlined,” Buchheit said. “The path that we were on wasn’t going to work.” Facebook’s offer looked good.

“As my mom explained to me, when two companies love each other very much, they form a structured investment vehicle,” Taylor wrote on the FriendFeed blog.

Facebook was still a private company, years away from its initial public offering. Molly Graham, who was working on mobile strategy at Facebook when Taylor joined the group, remembers him arriving with an intimidatingly swift intellect. Within months, Zuckerberg named Taylor chief technology officer.

“For Mark to do it in such a hurry speaks to how talented Bret is,” said Tim Kendall, a former Facebook and Pinterest executive.

Graham, who became Taylor’s chief of staff, recalled how he and Zuckerberg would rapidly ingest reams of data about mobile usage around the world. “One of the challenging things with him is that he’s very, very fast,” said Graham.

Facebook went public in May 2012, and Taylor announced his departure that summer. This time, he joined forces with another ex-Googler, Kevin Gibbs. Their new project was the talk of San Francisco. Taylor made the rare technical gaffe, accidentally revealing his new website that December by redirecting his personal blog to the new company’s website.

Gibbs and Taylor introduced Quip the following July to raves about the elegant mobile interface for creating and editing documents on smartphones and tablets. The mobile apps for Google Docs and Microsoft Word looked clunky in comparison.

“We’re still stuck in 1998 in that software and the rest of the world has moved on,” Taylor said at the time.

Quip won some fans, particularly among startups. By July 2015, 30,000 companies were using it.

Taylor came to pitch Kendall, then at Pinterest, and his CEO, Ben Silbermann, on Quip. “We ended up becoming pretty big users,” Kendall said. He recalled Taylor’s knack for demonstrating products and weaving in real-world examples: “He does it with such ease, it doesn’t feel rehearsed or anything.” His former colleagues at Facebook, too, became paying Quip customers.

Quip had an uphill battle selling to companies outside of Taylor’s familiar turf, though. Though Quip was hiring salespeople, it was outgunned by Microsoft’s Office-selling army. Google threw in Google Apps when businesses pay for Gmail.

Taylor had started a CEO dinner group that met every month. One of the attendees was Benioff, who had noticed Taylor’s departure from Facebook.

“When I heard it was going to be enterprise software, I was like, ‘What is he really going to do?’ And started to pay attention,” Benioff said. That turned into a $750 million offer to buy Quip in July 2016.

“I have to imagine Benioff was someone (Bret) wanted to work with,” said Muller, who had followed Taylor to Quip, along with Yang and Graham. “He didn’t need the money, he didn’t have to take the acquisition.” Taylor had worked at Google and Facebook before their initial public offerings, making his shares quite valuable. But the deal meant a big payday for his team, and the prospect of Quip reaching more customers.

Taylor told the Recode Decode podcast shortly after the acquisition that gaining “one of the largest direct sales forces in the world to be able to spread (Quip) to more companies is worth the trade-off of losing some of that independence.” He added of Benioff: “I think he’s a really wonderful human being and it’s not a huge tax for me to work for him.”

Initially, Taylor ran Quip as a unit within Salesforce. Then he began his ascent. Benioff made him chief product officer in 2017, and chief operating officer two years later.

“I’m lucky to have this guy around, it makes such a difference to have him,” Benioff said. “He’s such a great technology leader.”

When the pandemic broke out, Benioff asked Taylor to retool Salesforce products for the health crisis. The results are products that help companies to stagger shifts to keep employees safe in reopened workplaces; public health agencies to track vaccine distribution and trace contacts; and stores to manage queues and eliminate lines.

Taylor was also thinking about that same idea that animated him at Quip: the future of work. Better collaboration tools were newly urgent as businesses sent employees home to labor remotely. That’s when Stewart Butterfield, the CEO of Slack, reached out to Taylor. The question: Could Slack buy Quip?

The two had long known each other; Butterfield, who co-founded the Flickr photo-sharing site, remembered emailing Taylor to complain about FriendFeed’s bots scouring Flickr for updates a little too aggressively.

By 2014, Butterfield was running Slack, a general-purpose chat tool that connects employees with each other and the apps they use. Slack had already integrated some of Quip’s document-editing features; for example, it’s easy for someone who uses both to start a Quip document within a Slack chat.

Taylor and Butterfield talked about software they loved over the summer. Eventually, the conversation turned into a reversal of Butterfield’s proposal: Why not have Salesforce buy Slack?

Graham, who became Taylor’s chief operating officer at Quip and now has the same title at online learning startup Lambda School, said she had heard the deal came together with trademark Taylor speed, in four weeks. (The companies said they could not comment on the dealmaking process.)

“I think what we’re beginning to see is Bret’s real imprint on Salesforce,” she said.

The Slack deal is expected to close by the end of July, but Taylor has already made an impression on the employees of the smaller San Francisco software company who will soon work for him. They have already created a Bret emoji — a small icon of Taylor’s grinning visage. Such digital gestures are hard to interpret, but typically they’re an expression of affection.

“That is absolutely mortifying,” Taylor said, when informed of the emoji’s existence.

Taylor still finds time to program. In October, he created an Air Quality Reader app to make wildfire smoke readings easier to find. But he didn’t just code it up for himself, Muller, his friend and former employee, pointed out. He went through the trouble of writing up the documentation and jumping through the hoops of Apple’s App Store so anyone could download it. Not many executives at Fortune 500 companies can also call themselves iPhone developers.

He may well join his former boss Mark Zuckerberg in the rarefied ranks of hacker CEOs. Taylor wouldn’t comment on the prospect of becoming CEO of Salesforce, except to say, “I’m honored that people are talking about me that way.”

The people talking that way include his past and future employees.

“If I were looking for someone to take over a big company, he would be top of my list,” Muller said.

“It wouldn’t surprise me if he were CEO one day,” Butterfield said. “He seems really committed, he has a lot of energy. This is not (a case where) he stuck around because of the Quip acquisition.”

The FriendFeed crew loves to tell a story from their startup days, when “Mad Men” was all the rage. Could anyone, they asked each other, really have a three-martini lunch and work the rest of the day?

So the team walked to the Cantankerous Fish in Mountain View and started ordering drinks.

“I definitely have pictures of most of the employees passed out,” said Yang, who ended up marrying Muller after they met working at FriendFeed, with some encouragement from the Taylors, and is now studying traditional Chinese medicine. “I have a picture of Bret and Casey still at their desks coding.”

Taylor couldn’t recall how much code he completed, but admitted that a “competitive streak” may have kept him going.

He will need that, and more, at Salesforce, to see the Slack deal through and then turn the combination into something worth more than $27.7 billion.

Taylor, who said he grew determined to become a strong public speaker after freezing up during a mock trial session in high school, draws on his startup experiences when he’s ventured outside the world of writing code and dreaming up products.

“As a startup, you need to convince people,” he said. “Being an entrepreneur has helped me a lot with that.”

Owen Thomas is The San Francisco Chronicle’s business editor. Email: othomas@sfchronicle.com Twitter: @owenthomas