An Outsider from Insider Moves In at Fortune

When Alyson Shontell, co-editor-in-chief of Business Insider, was announced as the new editor-in-chief of Fortune in September, some of her Insider colleagues breathed a sigh of relief. “It was your birthday and Christmas rolled into one,” one Insider employee who asked to remain anonymous recalled. “Nobody I talked to was sad to see her go.” Not everybody was so gleeful; some were just surprised. “When somebody has been here that long,” said one editor, “you just feel like they’re never leaving.” Others were happy to see Shontell seize a new opportunity. They’d seen her slip down the hierarchy as Insider had restructured and thought she’d have a better chance to thrive in a different environment. Few, however, were looking to follow her. In the months since her departure, Shontell has had conversations with former colleagues about coming to work at Fortune, and not all of them have gone well. “There’s a big reason most of the people who worked underneath Alyson that she’s approached to come work with her at Fortune have said no — even if it means more money, even if it means a better title,” explained an anonymous Insider employee. “I’ve worked at a lot of different places, and she’s probably the worst manager I’ve ever had. Definitely, the worst at the level she was at.” Asked what sort of terms would induce them to join Shontell at Fortune, the employee focused on duration. “I would not do anything long-term because you’re probably not going to last,” they said. “Even if she doesn’t fire you, you’re going to want to kill yourself. So you’re going to leave within a year anyway.”

Many of the Insider employees who spoke to The Fine Print saw her taking the helm of 92-year-old Fortune as a sign of how far their 15-year-old startup has come. Insider has aggressively hired in the past few years, bringing on staff from some of the most respected newsrooms in the country and making people who’ve spent the majority of their careers there feel slightly provincial. “There are and were people who work here who were great when this was a little place with 12 people, and it was a bunch of people doing a tech blog,” said an editor. “I think there are people in editorial leadership, and I thought she was one of them, who are in way over their head at a place this size with what they’re trying to do, in terms of trying to be a New York Times or a Wall Street Journal. I had the feeling that she was doing her best, but I felt she was a little overmatched for the job.”

Fortune had been in flux for a while before Shontell arrived. Her predecessor Clifton Leaf was appointed editor-in-chief in March 2017 when the magazine was still owned by Time Inc. A few months later, that November, Time Inc. was acquired by Meredith Corp., which in turn sold off Fortune less than a year later to the Thai billionaire Chatchaval Jiaravanon. Last May, the magazine announced Leaf would be stepping down, with his deputy taking over the top job until a replacement could be found. Some staffers thought the company’s owners need not have looked any further. “We thought the acting editor-in-chief Brian O’Keefe would be getting the job. We didn’t know who else they were talking to, if anyone,” said one Fortune staffer who left the magazine after Shontell’s arrival.

Reactions within the magazine to Shontell’s appointment were mixed. Some were conflicted about the unprecedented nature of the first woman leading the title. “There was this weird, in my view, trepidation where it was like, ‘Oh, this is historic and it is cool that a woman, let alone a younger woman, is being hired,’” said John Buysse, an audience engagement editor and former Hillary Clinton campaign staffer who left the magazine shortly after Shontell took over to be a senior audience development strategist at Investors’ Business Daily. “I’m a very progressive person. I think it’s good to have diversity in hiring. But I think giving Brian the interim title created a huge mess for them, because there are other women at Fortune who probably are more qualified for Alyson’s job than her.”

In general, many at Fortune took a wait-and-see approach. “I don’t think I heard anyone say anything hopeful other than, ‘I won’t make a decision yet, I’ll keep an open mind,’” said a former staffer, adding that Shontell’s reputation at Insider had preceded her. “We definitely came in biased because we heard from people at BI that she skewed things in the direction of billionaires.” Bussye noted that that perspective was very much in line with what he understood about Fortune’s CEO. “Alan Murray is a lot like that. He is just obsessed with CEOs and rich people,” he said. “I think that must have been one of the things that appealed to him about Alyson.”

---

Shontell’s history with Insider goes back to when she joined at age 22 in 2008, the year after the company was founded as Silicon Alley Insider. She worked as a sales planner for her first two years, then she moved toward editorial, focusing on tech coverage. The strong bonds she formed with the company’s founder and CEO, former Merrill Lynch stock analyst Henry Blodget, profoundly shaped the rest of her time at the company and shielded her from some of the dissatisfaction around her management style. “Henry Blodget was never going to fire her because there was loyalty, trust, a whole lot of things going on there,” said a staffer. A belief that speaking openly about Shontell could damage employees’ careers at Insider even after her departure was apparent in the reporting of this article. Insider staff who had worked with Shontell would not be quoted without being granted anonymity. Others spoke only on background, even when they had largely positive things to say about her.

By the time she was promoted to editor-in-chief of Business Insider in 2016, her management style had taken on a recognizable shape. “Her style was a little mincy. She was a bit of a control freak,” said an Insider editor. “It felt a bit oppressive.” Every current and former Insider employee who spoke with The Fine Print for this story described Shontell as a micromanager, as one put it, “down to dictating out exactly what the headline would be.” But she was also said to give unclear instructions. “She was also very bad about giving you very vague and broad mandates,” an anonymous employee said. “Basically, you learned what she wanted more by what she told you that she didn’t want.” In the eyes of that employee, the friction around her in the newsroom came down to her general management philosophy. “I think that she has this idea of leadership, that leaders are not supposed to be friends with people that you manage — and that’s true. They’re not your friends, at the end of the day. They’re people that you manage. But she has this idea that it’s okay to be hated,” they said. “She saw that people did not like her and sort of accepted that as just part of the job.”

Those bad vibes weren’t universally felt. Some were surprised at how approachable Shontell was for a news executive. While some resented her meddling with their stories, others welcomed it, noting her talent for headline writing and framing. And they said that her co-editor-in-chief, Matt Turner, could also be a very involved boss but that he’s more widely liked and hasn’t been accused of micromanaging, perhaps because of the gender difference. Even people who didn’t enjoy working with Shontell struggled with how that gender dynamic fits with their feelings towards her. “This is where the guilt sets in,” said an Insider editor. “I’m trying not to attack a top editorial leader who is also a woman because I think it can look kind of bad, too. I’m trying to separate that out.”

Even employees who generally liked Shontell noted her tendency to sympathize with the rich and powerful in coverage. Some saw this as a mandate that originated above her. “I think that was more of a broader leadership thing,” said an editor. Others saw her as taking it particularly far. “It’s fair to say that we should strive to tell objective, fair stories so that not every single CEO or every single founder is evil. Malice isn’t behind everything, sometimes there’s just incompetence, I think that probably goes for Alyson as well,” said an employee. “But on the day-to-day level, there was never a sense that if you told a story that treated labor badly or that treated workers poorly, you would get in trouble. If you wrote or assigned or were a part of a story that treated a VC badly or a founder or a CEO, and they wanted to yank your chain, Alyson would be happy to aid in the yanking.”

An instance of this tendency, the employee recalled, involved a story about the digital wealth management firm Ellevest which the employee claimed Shontell had altered after publication. A capture of the article on the Internet Archive’s Wayback Machine reveals changes to the version currently displayed on Insider. “Inside Ellevest: Why $80 million and one of the most powerful women on Wall Street isn’t enough to stand out in the crowded world of wealth,” was the original headline. In the updated version, it became “How a female-focused wealth firm founded by one of the most powerful women on Wall Street with $80 million in funding faces an uphill battle standing out in the crowded world of wealth.” Language in the original saying the story’s purpose was “to understand why Ellevest’s mission didn’t gain more traction in the ultra-competitive business of managing money” in the updated version became “about the rise and positioning of Ellevest in the ultra-competitive business of managing money.”

According to another person familiar with the situation, the changes were made after a subject of the story contacted Insider, and none of them involved a correction. “Alyson basically went in on the weekend and inserted some puffy quotes to it without talking to the reporter,” another employee said. “So the reporter found out and was like, ‘What the hell?’ Then Alyson had to go in front of the finance team and explain what she had done.”

In response to a list of questions The Fine Print sent to Shontell regarding the post-publication editing incident as well as other staff criticisms cited in this article, a Fortune spokesperson declined to comment on behalf of Shontell and her magazine. Mario Ruiz, a spokesperson for Insider, confirmed that changes were made to the Ellevest story after publication but couldn’t provide details on why. While acknowledging that they’d picked up on this bias from Shontell, other staffers at Insider recalled her supporting them when they told unflattering stories about powerful people.

Prior to Shontell’s departure from the company, broader restructuring had pushed her down the org chart. In October 2017, Nicholas Carlson, who had until then been at a similar level to Shontell as the editor-in-chief of Insider, a general news sister site launched in 2016, was made global editor-in-chief of Business Insider, and Shontell was shunted under his aegis. (Last year, the entire company, controlled by German media company Axel Springer since 2015, rebranded to Insider.) The interactions between Shontell and Carlson did not leave a friendly impression on some observers. “It was very clear that Nich didn’t have a ton of respect for her,” said one staffer. “Nich likes everybody, or at least comes off like he likes everybody. He’s like a golden retriever. And so, for there to be palpable — it did not seem like they got along.” They speculated that part of that might come down to their professional leapfrogging. “I think there was also a lot of heated rivalry,” they said. “At some point, Henry [Blodget] made a bet that Nich was going to be the horse that was going to run and Alyson wasn’t.”

Carlson denied that there was any animosity between the two. “I will always be grateful to Alyson for her friendship and the work she did to change our newsroom for the better,” he said in a statement to The Fine Print. “The two of us are very much in touch — and figuring out when our next drinks will be.”

In October 2020, Shontell’s position was diluted when her executive editor Matt Turner was promoted to co-editor-in-chief of Business Insider. Shontell celebrated Turner’s promotion in the announcement. “I have come to see Matt as more than a report. He is a true partner,” she wrote. “A true partner deserves ownership and a chance to lead.” But others at Business Insider saw it as a development that did not bode well for her future at the company. “It was super clear, when I would talk to other people at my level, that everybody saw it as Alyson slowly getting shoved out the door, in some form or fashion, even if it would take a while,” said an anonymous employee. “This was setting everything in place for Alyson to eventually go do something else, either by her own choice or not.”

---

Some at Fortune were enthusiastic about the announcement of Shontell’s appointment. “I was excited to work with her. I had been pitching her on a big expansion of Fortune’s crypto arm. She seemed to be on board for it,” said Robert Hackett, a senior writer and tech editor who left to work for Andreessen Horowitz in November. “Then this other opportunity arose, and I just couldn’t say no.” Shontell had made a good first impression with the staff by taking one-on-one calls with her new employees before she officially started the job. “I think everyone really appreciated that,” said a former staffer, “I felt good about my talk with her.”

But soon, the tendencies that were familiar to her Business Insider staff began to pop up. “She was immediately Slacking people in off-hours, demanding that they do things outside of their jobs,” a former Fortune staffer said. “She was very involved in headline writing in a really weird way, giving a lot of directives. This is just not how anyone who’s ever worked in a newsroom experiences an editor-in-chief, especially a new one.” Bussye pointed out the pitfalls of that micromanagerial approach. “Everyone was open to this digital mind coming in,” he said, “but it seems like she was so focused on small things that it was like, ‘Wait, are you doing larger strategic changes? Why are you so focused on this random headline and tweet right now?’”

Shontell, former employees said, had different expectations than were standard in Fortune’s culture. “We had never been people who were forced to work nights or weekends — obviously, a lot of times people did — but she was forcing people to do that right away,” a former staffer said. “I got on a far higher dose of my anti-anxiety medication shortly after Alyson started. It was seriously the worst time of my life.”

One of the factors that had primed the staff for a backlash against their new boss was that Fortune had been understaffed, at least since cuts early in the pandemic. While Insider boasts a global team of 500, Fortune’s masthead is less than a fifth of that size. “Our staff was so small, yet being asked to do more and more at all times,” said Buysse. “I don’t think she realized that she was already with a fully burnt-out staff.” On the flip side, this meant there was room for Shontell to bring new people to the masthead. Some new hires, like director of audience Ashley Lutz, had worked with Shontell at Insider before departing to work elsewhere in the interim. Others, like executive editor for news Nick Lichtenberg, who had been a deputy editor for economy at Insider, followed her directly. His colleagues weren’t particularly surprised that he left. “Nick was definitely a climber. He already got, frankly, an early bump up to deputy because he went and got a job offer and then used that to counter, a little bit before I think he would have normally gotten it,” said an Insider employee. (Lichtenberg declined to comment on that.) “He’s still young enough to have some ambition in the world,” said an editor. “I think the chance to have the executive editor title spoke to him, and that was probably not something that was going to happen here in the next six months.”

Lichtenberg said he reached out to Shontell about coming to work for her last year. She’d been the person who he had his first interview with when he joined Business Insider, but he’d spent more time working directly with Turner. “Insider is a very big organization, so I feel like Alyson was a pretty friendly face that I would see from time to time,” he told The Fine Print. “We always had a good relationship, and she treated me with a lot of respect.” But leaving Insider wasn’t easy. “It was a hard decision, but an exciting opportunity,” he said. Asked what it was about Fortune or Shontell’s vision for the magazine that attracted him to it, he was noncommittal. “I don’t know,” he said. “I prefer not to say.”

Shontell’s former colleagues from both Insider and Fortune have a pretty set idea of her vision for the magazine. “One of the reasons that I was like, ‘I absolutely have to get out of here,’” said Buysse, “was that she is going to turn this place into Business Insider 2.0, even though it’s just not the same brand.” A former Fortune reporter who asked to remain anonymous agreed. “Insider is a much bigger operation that pumps out stories like crazy,” they said. “I don’t know how they plan on making Fortune into something comparable without drastically overhauling the organization.”

Some at Insider are more curious than dismissive. “We’re all sort of thinking she’s just going to make an Insider over there,” said an editor. “I am interested to see how she builds the thing, and what it looks like, and where it overlaps with what we do and what we do not.” Others at Shontell’s prior employer have regarded her progress with residual anxiety. “She has to stand up what Insider is doing at Fortune, and what Insider has been doing, particularly over the past four or five years, takes a long time, takes a lot of effort, skill, talent, and money. I don’t know if she has it in her,” said an anonymous employee. “I sincerely hope that she succeeds at Fortune, because I do not want her coming back to Insider, and I’m not sure where else she would go.”