Why ELLE.com's deputy editor spotlights 'extremism of all forms'

Behind Jessica Roy's brilliant story on an American woman's unlikely ISIS connection

Hello, happy back-to-school time! For our ~September issue~ we’ve got an interview with ELLE.com’s deputy editor Jessica Roy. Roy’s outstanding 10,000-word piece published last week about two American sisters, one of whom faces federal terrorism charges for allegedly aiding ISIS, has been making serious rounds.

While Roy is responsible for assigning/editing at one of the best digital media sites for women, she is diligently reporting pieces, which probably contributes to the great reputation she has among writers. She previously worked as news editor at The Cut, and before that at TIME and The New York Observer. And now, we can all support her idea to frame the below tweet.

That’s all for now — TGIF!

xx Natalie


Q&A with ELLE.com’s deputy editor Jessica Roy

Some people (according to Google, T.S. Eliot) say editors are often failed writers. Yet you recently published an impressive two-part series about a pair of American sisters dealing with one’s unlikely move to Syria where she lived under ISIS. What motivates you to write long, especially if it's not a core job responsibility? 

For me writing and reporting long features is an escape from the monotonous churn of online news. You can only edit so many posts about “X Celebrity Did Y” before you start to feel a little bored. I think doing deep dives into specific topics or writing longer stories gives me a much-needed break from the news cycle. It also helps give my brain some time to recalibrate.

How did you first become interested in the Sally sisters, and what was your 8-month reporting process like? 

I’ve been writing and reporting on women in the Middle East for some time, including the small group of western women who moved to Syria and Iraq to join ISIS. I heard about Sam last summer when she was first brought back from the refugee camp. I was so curious about how she ended up in Syria, and when I started talking with her sister Lori, I began to realize it was a much bigger story than I’d initially envisioned. For the first several months I only had contact with Lori and several of Sam’s friends and ex’s, but towards the end I was able to speak extensively with Sam and some of her other family members, which really helped me round out the reporting.

How did you decide on the story’s structure, and to divide into two parts? 

My editors (shout out Ryan D’Agostino and Kat Stoeffel) really helped me hammer out the structure. When I filed my first draft I had a different lede that started with Lori getting the email from Sam about being in Syria, but together we realized it would unfold more elegantly if we told it from present day, back into the past, and then back up to present day again. And honestly we decided to break it into two parts because it was so long! Together the two parts are more than 10,000 words, which has to make it one of the longest things ELLE.com has ever published. Scrolling through a 10,000 word piece on mobile—which is the platform the majority of our readers read the site on—seemed like a nightmare and might make the load time crazy long, so we thought splitting it into two parts would make it easier to navigate.

In what ways did gender or the shared lived experience of being a woman most shine through for you? 

I think it was clearest in Lori and Sam’s relationship as sisters, and how complicated that relationship is. I’m one of four girls, so I know how fun and amazing it can be to have sisters, but I also know how frustrating it can be, and how much rivalry it can breed. That was a theme I really wanted to tease out throughout the whole narrative–the power of that sister relationship, and what its limits are.

What has the reception been like, and what are your plans to keep following Samantha Sally’s trial? 

The reception has been really incredible. I was worried that nobody has the time or energy for a 10,000-word story anymore, especially a 10,000-word story on a site that’s not like, The New Yorker. But it was one of our top stories of August, and got a ton of pickup and praise, so that’s something I’m really proud of. I’m planning on covering the trial when it starts in January, and perhaps working on expanding it into a book—stay tuned.

Why did you begin reporting on women and the Middle East and studying Arabic? How are you keeping up with what’s happening in their world right now? 

I took a lot of Middle Eastern Studies classes in college and have always been interested in the region. I started focusing more heavily on it in my reporting about three years ago, and started studying Arabic about a year and a half ago. I have a lot of friends in the region that I spend a not insignificant part of my day chatting with, and I read a ton of MENA-focused news outlets, like Middle East Eye. I also try to make as many trips a year to the region as time and money allows. So far in 2019 I’ve been to Morocco and all over Turkey, and in November I’ll be spending a week in Jordan and a week in Lebanon. Last year I did parts of the Gulf—Saudi Arabia and Dubai.

How does working at a more “legacy” outlet like Elle compare to working at a newer, first-came-blog The Cut? In terms of writing/editing, what are the benefits of being a player-coach at outlets like ELLE.com and The Cut? 

It’s not that different, except that at legacy outlets there are usually more resources (and more red tape!). I love sharing an editor/writer role because when I’m managing my team of writers I know exactly what they’re going through and can tailor my edits accordingly.

You’ve written about everything from tech, media personalities, and a cultural analysis of women who owned “being underestimated”  — plus comedy. How would you describe your range or subjects that interest you? 

I’m kind of a generalist—any time I find myself with a specific beat I get bored and want to pivot, so I like to keep what I write about pretty open-ended. Recently I’ve been very interested in extremism in all forms—religious, social, political—so I find a lot of the things I read and write about relate back to that in some way.

Real talk: how do you run a team, actually have hobbies, and keep up with what’s going on with celebrities? 

Well it’s easy to keep up with celebrities when part of your job is keeping up with celebrities! But in general I’ve always been very regimented, so I think once I find a way to work something into my daily routine, whether it’s working out every morning or going over my Arabic flashcards every night, I find it pretty easy to stick to.

Time for shoutouts…Who are a few people who helped you grow as a leader, and how? And what media aimed at women or nonbinary folks are you consuming right now?

ELLE.com’s former Digital Director Leah Chernikoff is now head of content at Glossier, but she brought me on to be her deputy last year and I learned so much from her about how to lovingly manage a team of women. Kate Seelye at the Middle East Institute has also been so wonderful helping me ease my way into reporting about the Middle East. And my mom has always had her own business and been her own boss, so I think watching her balance being a leader in her field with taking care of me and my sister really normalized it for us and made it seem achievable. In terms of media I’m consuming and loving, I still think The Cut is one of the best women’s websites out there. And of course, ELLE.com. :)

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