In our long-running series “How I’m Making It,” we talk to people making a living in the fashion and beauty industries about how they broke in and found success.
When it comes to digital lifestyle media, Simone Oliver has established herself as a force to be reckoned with. The Howard University alum began her career by assisting at nearly every desk at the New York Times — the English major’s answer to journalism school — and went on to lead the paper’s Styles section into the digital revolution, including establishing the paper’s first-ever Instagram account (despite push-back from higher-ups questioning the platform’s ability to drive traffic).
After 13 years at the Times, Oliver went on to help Allure navigate its own digital transformation. She followed that up with a stint on the Global Media Partnerships Team at Facebook and Instagram, where she continued to help magazines and lifestyle publishers formulate their digital strategies.
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Much of her career has been defined by media’s changing tides, and her latest role is no exception: Last September, amid a global pandemic, she became global editor-in-chief of Vice Media-owned Refinery29, where her predecessor stepped down amid accusations of racism and a toxic company culture. Meanwhile, Oliver works as an adjunct professor at Syracuse University’s S.I. Newhouse School journalism program.
We caught up with Oliver a few months into her new job via phone to discuss how she’s approaching leading a global media company (and trying to help correct its internal issues) from home, “working in digital when no one cared about digital” and how one woman inspired her to jump back into publishing after working in social media. Read on for the highlights.
How did you get started in media and journalism?
I went to Howard University in D.C. I came in as an English major and psych minor. I quickly got bored with Shakespeare and Chaucer — respect those guys, but I definitely started seeking out different types of writing. I also noticed I was pretty good at editing. So my side hustle was editing other people’s papers for money, in addition to the usual ethical jobs. I also worked at the school paper, and I think that’s where I really got my journalism chops. I wasn’t in Howard’s school of communications, but there was a point later on in my academic career where the editing classes offered weren’t available to English majors. I basically campaigned to be able to take those, and eventually they let me do that, so I was able to get those credits. That and writing for the school paper, covering all different beats, I would say were my journalism training wheels. And those are probably the seeds of my career aspirations.
Then at the end of school, I had learned about a new program that the New York Times was getting off the ground, called The New York Times Student Journalism Institute. Like a typical college senior, I applied the day before the deadline. I had to send my applications and essays and all that overnight, which is very expensive for a college student. I eventually got into the program. We were the first class, sort of the guinea pigs of the program. It was half internship, half bootcamp: Thirty students from schools around the U.S. come together and create a student version of the New York Times under the guidance of the New York Times editors, design, multimedia, copyeditors, reporters, etc. So, yeah it was wild. I would say outside of having kids, it was one of the most intense experiences I’ve ever had in my life. But it really cemented my passion for journalism and editing. That’s when the flicker inside of me kind of lit up. I was like, ‘Oh, this is what I want to do.’
How did that turn into a job?
When I left school, I reached out to the head of the program — who was also the head of the copy desk at the Times during that time — just to get a sense of how I can make my resumé pop. Now that I’ve figured out I wanted a career in media and journalism, I didn’t have the typical three semesters of NBC and Washington Post under my belt, so I was really concerned about finding a door that was open. So, I reached out to him, did a lot of emailing and faxing my resumé to people at that time and got my start there as a news assistant. I spent almost thirteen years there and had a bunch of different jobs.
I worked at every single desk across the paper. That was like journalism school to me. I understood better news judgement and how to write headlines, what makes a good story, all of that — copy flow, the operations and business of journalism as well. But it was there that I started to become obsessed with copyediting, and I kind of simultaneously outgrew my role as an assistant.
Then, after a lot of conversations and experiences, I moved onto the web team, which was separate back then. We were in completely different buildings. So, again, it was like the guinea pig theme. That was right around the time New York media in general — and the media industry at large — was going through the big transition [to digital]. It was a wild time, especially to be at one of the leading publications [that was] also very, very legacy. There was a big, not just philosophical disconnect between print and digital, but also cultural. Before I started at the website, I read ‘HTML for Dummies’ because I had the editorial groundwork and foundation and a little bit of experience, but in my mind I was like, ‘I don’t code.’ So that ended up working out. I spent the next couple of years tackling the white space of digital.
Eventually, I got promoted to digital fashion editor. I started thinking about what the New York Times‘ style footprint in digital was as a whole, as opposed to, ‘Let’s just put up the one story that went in the paper.’ That’s when I really started to define the digital content strategy. Then down the line, I became editorial lead for the iPad app, when those were a thing. I started the first Instagram account across the paper — at the time, that was @nytimesfashion. It was just something I felt like we had to do, because if we were looking for that next generation, and also to be so visual, that was a good platform for us to be on. I felt like we could lead there. It was met with some contention. They were like, ‘It doesn’t drive traffic.’ So that really transformed our digital-first content strategy. Because I had done a couple of big projects, including live red-carpet coverage that gained the trust from a lot of the senior editors and leadership there, I started getting budgets. I was able to deploy small teams for fashion week specifically for digital content — the same thing for red-carpet season. That was a really fun time. After that, I joined the audience development team as part of a small squad of what were called ‘growth editors’ at the time.
I was really, really excited about what I was doing but internally, I had this tension where I felt comfortable because I felt like I knew what I was doing, but I also felt like my growth was beginning to plateau a little bit. Not that I was above and beyond anything — just that my growth acceleration wasn’t as fast for me to be so mid-career. I started talking to Condé. They had recently hired Michelle Lee to lead Allure, because they were going through their own digital transformation, and were looking for a digital director to usher that in. I moved over there as digital director, my first time going to a new company after sort of growing up professionally at Times. As soon as I started, I hit the ground running with the relaunch, re-platforming, hiring a new team. Really fun, very intense, but I had oversight across the site, so that was a good experience. And then I went to Facebook. And never in a million years did I imagine myself at a platform.
How did that jump happen?
It was a mix of things, but one of my good friends who had been there for years — a former journalist as well — had been trying to get me there for a while. I was like, ‘Mmm, I don’t see it. Like, my dream is to be an editor, and I’m an editor, I love what I’m doing.’ But then, they had started a new role in their partnership team that was focused on magazines and lifestyle publishers, and that spoke to me. And I think also at that time, I had become a little bit fatigued of the digital media grind, where I was just run down to the bone and was looking for something a little bit different. I didn’t really know that until they reached out.
What were some of the most striking differences going from media to a social media platform that’s also this big corporate entity?
I would say initially, it was the pace. Someone told me, ‘Oh this place moves fast’. I’m like, ‘Yeah, digital media moves fast.’ When I got there, the pace was crazy fast. I would say the diversity of backgrounds as well — sometimes in media, you have a lot of people who come through journalism school and internships, all very similar paths. But there, it was exciting because I got to talk to people from all walks of life. And then there was the global emphasis of the company too… I started to get a better education there, which was super exciting. And the business model: Facebook, Instagram, media companies, talent agencies, the NBA, all these different organizations were thinking about what their innovation and their business model innovation looks like. That was a big difference.
Were you mainly just helping media companies formulate their social media strategies?
Exactly that. Constant, constant meetings. And it would be all walks of life within a media company. Some meetings would be with a CEO or president of the company to talk about top-line strategy, how their audience development strategy aligns with their business goals and helping them at a very succinct and high-level way, how to navigate the platforms especially because they change so fast. And then it could be doing an activation with a social media director at any given brand who wanted to celebrate a tentpole and wanted to try something innovative to better reach and better engage with their audience.
Did you see yourself staying in that role or in that realm, or were you on some level itching to go back to media?
I wasn’t itching. I had just come back from maternity leave and I actually felt really good and renewed coming back into the office in February. A little bit later, Covid hit, and I was working from home. Then I got the call from a couple folks at Vice, Cory [Haik, chief digital officer at Vice Media] being one of them. And Cory is someone that I have long admired in the media world — like, what she did at Mic. She’s just someone who I was like, ‘If I ever have a chance to work with her, I would seriously consider it.’ And I remember when Vice announced that they had hired her as the chief digital officer, and I was like, ‘Good move, Vice, I see you.’ I always pay attention to women in the industry who I’m like, ‘I can learn from this person.’ So we talked and talked and talked and talked some more. As comfortable as I was at Facebook — as good a time as I was having, as much as I was learning — I had to be honest with myself that this is a dream that I’ve always had. So, if I’m 80 and I don’t seriously consider this, will I regret it? And the short answer is yes. So here I am.
Obviously, you started this job at an interesting time, for a lot of reasons — starting a job in a pandemic, remotely, and also considering the circumstances that lead to the previous editor leaving and the criticism Refinery29 was facing in terms of the work environment there. What was it like navigating that, as well as a new job?
Obviously, Covid makes it most tough because you’re not there in person to just listen to people and be present, especially when people have had sort of a tough year. I think it just comes down to trust and transparency. What I’ve really had to focus on is building that trust as a team. And I’ve tried to have open communication, be really transparent about the changes that are happening in the company, how I manage, my ideas — just having conversations. It’s a lot, because you’re at home and you’re on Zoom. You can’t do coffee walks, you can’t do ice cream walks, which is my preference. Especially for the remote teams [in] the other regions. Even though we’re all remote on Zoom, it’s different when you’re in another office that isn’t the headquarters. So I always want to make sure all of R29 feels connected.
Also for me, leading with empathy is a big deal. You can’t really identify pain points or problems without understanding the type of challenges people are faced with on a daily basis.
Can you share a little bit about what your overall goals for Refinery29 are, and what may be some things you’re excited about or proud of having achieved or overseen already? Then, what are you still hoping to do in the coming months and years?
I guess the main goal and the north star that I keep coming back to is that it’s really important for us to create a space for women, for underrepresented voices to be seen and heard. And more than just that, we want to make a direct impact in their lives. And we also want to celebrate expression, which has always been a part of what Refinery’s been about, and I want that to stay. The other thing is thoughtful storytelling across platforms is really important to me. We have a lot of existing franchises and IP and topic areas where we have authority, things that we’re known for. But I really, really want to continue to develop new ways to serve our audience.
Our Unbothered team had a really impactful program — this is kind of what I mean when I say making an impact in people’s lives — called Buy Black at Facebook. And Facebook just had their Buy Black initiative. To be clear, it wasn’t like, ‘Oh, as soon as I go to Refinery, I’m gonna do something with Facebook.’ It happened organically. It’s something that we both wanted to support, and that didn’t just seem like a random partnership for our audience. [We wanted to] serve the Black community, especially because Unbothered is always thinking about closing the wealth gap.
Then, we just introduced alt text to improve accessibility across our site. What that means is no matter how you’re coming across our site, for example if you’re blind, it will display what you’re looking at. So we talk a lot about inclusivity and accessibility, and it’s really important that we put our money where our mouth is, in ways that really matter and affect day-to-day audiences.
We’re spending more time with an increased focus on Unbothered and Somos. We have a lot of trust among our audience and crazy engagement, and we want to make sure that we continue to build that relationship. We don’t see any of our brands or any of our conversations across Refinery as one-way broadcast channels. It’s always a conversation beyond buzzwords like ‘engagement.’ Our audience holds us accountable.
And then, we have a lot of authority in the work and money spaces, Money Diaries, for example, where people can learn from each other and have real talk about their careers and finances, especially when they need it most, i.e. the Covid economy.
Lastly, in January, we launched Wash Day. Our beauty writer, Aimee Simeon, started this column and we turned it into an experiential day where we spent half a day with our Unbothered audience, sort of riffing around the ways we connect with our hair, but also about their mental well-being. For me it was a big deal to do this experiential event because a lot of people have Zoom fatigue. There’s a lot of panels and a lot of events that people are trying to activate, but for us, again, by listening to our audience, it was all about, what do you need right now?
You mentioned, your audience keeping you accountable. Do you feel like that creates added pressure for you to make sure you’re living up to every single expectation that readers might have for Refinery as a company, both in terms of content and what you’re doing internally?
Not really… I’m always aware because I respect our audience. That’s who we create for. But I think as long as we continue to be transparent and make sure that our values and our goals remain the same, that doesn’t really change. Whether or not someone chooses to weaponize Twitter or Instagram or something, that’s one thing, but as long as you hold yourself accountable and hold your team accountable and keep moving one foot in front of the other in terms of positive momentum, that’s going to be be my north star.
Looking back on your career, what would you say has been the biggest challenge so far? And what was the most rewarding moment?
Definitely Covid, and then working against the exhaustion to try and unearth information. That to me is the biggest challenge, because even on the days that you wake up and have all of these ideas, sometimes you’re just really lonely and feel really isolated. Maybe your inspo button is flickering. I would pay money to have ten minutes alone. So, we’re all going through our own things.
In terms of most rewarding moments, I think there have been times where, especially when I was younger and I had less confidence, I had an idea or I felt strongly about the direction that we should be going in, and I did my homework and I trusted my gut and then sort of let my curiosity guide me and it paid off. I hate to be that person like, ‘It always paid off!’ But it did. And when that kept happening. [What I’m] referring to is working at a time in digital when no one cared about digital — people didn’t see value in it, and just [me] seeing, ‘Okay, no, people spend a lot of time on the internet and storytelling can come in many different mediums,’ and being able to still do my homework and have data and proof points to support what I’m talking about. But really, really trusting my gut and letting my curiosity guide me.
What do you look for in a new hire?
Curiosity, hustle, integrity.
Beyond that, is there any advice you would give someone who wants to work for you?
My career advice would be put your imagination cap on as long as possible or have it on as much as possible, and allow yourself to think big. Also, pay attention to the winds of change. Because sometimes it’s a breeze and other times, it’s a full-on gust of wind.
Where do you see your career heading from here? Do you have any specific career goals that you haven’t already achieved that you hope to in the future?
I would say when I came to Facebook, I didn’t know what I wanted to be when I grew up anymore, and I allowed myself to be open. I also ended up having another kid. And so, that was sort of my open time. Right now, I’m really committed to this role. I’m just as excited and anxious about all the opportunities as I am the challenges. I see myself in this role for a bit.
I want to continue teaching. Because every time I think I’m gonna stop, I have a class and I’m like, ‘Oh my goodness they’re amazing.’ I learn as much from my students as I try to teach them. And I would like to write a book in the near future.