“There wasn’t an obvious position for me,” Scott Amenta said.
Mr. Amenta, 30, was describing how five years ago he joined Spring, an e-commerce company so small that its employees could be counted on one hand.
Around that time, a mentor advised him to keep an eye on the nascent chiefs of staff in technology world. People in that position were seen as the next wave of founders, he was told. Reid Hoffman (the influential LinkedIn boss) had one! So did the Winklevoss twins!
So Mr. Amenta asked to be named chief of staff.
In 2016, after toiling patiently in business development, he got the coveted title, and took up a position that is suddenly everywhere. In the past half-decade, chiefs of staff have marched from the military and the halls of Congress into the technology world and beyond.
“There’s something about the title or the idea of the chief of staff that seems to be in the zeitgeist,” said Chris Whipple, the author of “The Gatekeepers,” a 2017 history of White House chiefs of staff. “I’m encountering more and more, not only in the political world but in the corporate world.”
The chiefs have advanced into banking, art, theater and media. The director of the Whitney Museum of American Art has one, as does the publisher of The New York Times. And they are storming start-ups with particular ferocity.
Rachel Peck, 30, got the chief of staff job at the razor company Harry’s in 2015. (She had also heard about Mr. Hoffman’s chiefs.) Now, she said, Harry’s has two chiefs of staff and will soon have three.
Julie Samuels, the executive director of Tech: NYC, a local network of technologists, said that the founders and chief executives have become more like politicians or movie stars, having to interact with the public a lot at conferences or in the news media.
“Part of why you see all these chiefs of staff is they’re helping to do the work that isn’t getting done,” she said.
Soon after receiving the title, Mr. Amenta helped found the COS tech network, a forum of staff chiefs. Its inaugural dinner, at the Smile on Bond Street in Manhattan toward the end of 2016, was attended by about a dozen people. There are now close to 200 members.
Alter Egos
In the past several decades, chief executive compensation has increased exponentially. In technology, that trend has joined with the so-called cult of the founder, a phrase used recently regarding Adam Neumann, the ousted co-founder of WeWork.
Mr. Neumann’s former chief of staff is suing him for discrimination. WeWork, also, has multiple chiefs of staff. The company declined to comment.
Ms. Samuels’s chief of staff, Sarah Brown, 34, said that in New York, the title may have become popular in tech thanks to a broad exodus of people who had worked in politics. Ms. Brown herself used to work at the Democratic National Committee and founded the COS network with Mr. Amenta.
“We’re at this moment kind of post-Obama where a lot of talented work force found themselves moving from government into start-ups,” Ms. Brown said. “I have a couple of friends who were pretty high up in the Obama administration who have come over as chiefs of staff.”
Then, too, there is simply the ever-closer relationship between government and business. While he was the deputy mayor of New York City, Daniel L. Doctoroff went through four chiefs of staff.
“They all were viewed as my alter egos,” Mr. Doctoroff, 61, said. “People understood very clearly that when each one of them spoke, they were speaking for me.”
When he became the head of Bloomberg in 2008, he brought the position with him. He is now the head of Sidewalk Labs, an organization owned by Alphabet, the parent company of Google. His chief of staff is Nate Jenkins, who was previously a chief of staff in the Office of Management and Budget at the White House.
”It’s the best leadership course you could potentially take,” Mr. Jenkins, 37, said of the role. (He was on the same phone call as Mr. Doctoroff.) “It expands my original capabilities. I am expanding how I both take in information and make decisions.”
Who’s in Charge Here?
Like the creative director, the position du jour about a decade ago, chiefs of staff can be powerful, or not. They can be among the leaders of a company, or not. Frequently, they are not actually in charge of staff. They can be on the executive team, off the executive team, or, like Mr. Amenta at Spring, “straddling the executive team.”
They are often former executive assistants. Beth Kurteson joined Winklevoss Capital in 2013 as an assistant and became chief of staff in 2014. Now she is the “managing director of operations, people strategy & growth.”
“No chief of staff is the same,” Mr. Amenta said.
There are similarities, though. Chiefs of staff tend to help field and minimize their principal’s duties. They often mediate between that person and the rest of the world. Mr. Doctoroff called his chiefs of staff a “conduit.”
“Generally the chief of staff is a foil to the principal, to supplement him or her,” said Dennis Yu, 35, a two-time chief of staff, first at Betterment, an investment app, and now at Chime, a banking app.
Like a weird kind of work twin? “Yes,” Mr. Yu said.
Given how vaguely the role is defined, it can be subject to discriminatory practices. Mr. Amenta’s network conducted an internal survey and found that while women who were chiefs of staff tended to have more experience, men in the role tended to earn more.
But some chiefs argue that it’s a particularly good position for professionals who have been marginalized in the past.
Tani Brown is the chief of staff at Jopwell, which helps companies recruit racially diverse employees. While she did not think her success in the role came because she was a woman of color, she said that “it gives me a unique advantage.”
“Since I’ve been privy to meeting other chiefs of staff, especially in New York City, I’ve had a chance to meet other women of color in this position,” Ms. Brown said. “A lot of women of color have commented that it’s been a remarkable opportunity to influence.”
Ms. Peck, the former Harry’s chief of staff, is now a director at the company.
“The more that this has become a role that people understand in the world, the easier it is to explain what you do and to make the case for what you should be doing next,” she said.
Still, the chief of staff corps is angsty about next steps. One of the more popular of the articles Mr. Amenta has written for his network on Medium has the headline: “Is ‘Chief of Staff’ a dead end role?” (His answer, essentially, is yes.)
“I don’t know very many chiefs of staff who have done the job more than once, certainly not twice,” Mr. Yu said. “Most people will forge a path themselves into a new function.”
