By Heather Taylor For the past three years, Gina Vaynshteyn has made breaking into digital media look super easy (and incredibly fun) as the editorial director at HelloGiggles. As a fellow HG writing alum, I’ve been in awe of the site’s evolution since it launched in 2011 and how many positive changes have been made under Gina’s leadership.
If you’ve ever dreamed of working at the startup created by business partners and friends Zooey Deschanel, Sophia Rossi, and Molly McAleer, this interview is for you. We’re deep diving into how Gina first got involved with HelloGiggles, what a typical day at their West Coast office looks like, and the launch of their first print magazine. And, if the title didn’t already tip you off, we also have a sneak peek at Gina’s new gig!
Can you tell me more about your career background?
I was in grad school for creative writing when I discovered I could write words for the Internet and (eventually) get paid for them. It was a revelation. My first published piece online was a poetry book review for The Rumpus. The next, a “From Our Readers” essay for HelloGiggles. I wasn’t paid for either of those stories, but just seeing my byline for the first time was an amazing feeling. One freelancing gig (paid this time) led to another and by a certain point, I knew I desperately wanted a career online, specifically in digital media. There seemed to be so many opportunities and open doors I didn’t even knew existed. I had found something that I could see myself doing and loving forever.
Before you came on board to HelloGiggles, you freelanced with sites like Bustle and Mic. What kinds of topics did you cover?
I covered everything and anything, but mostly lifestyle content, with some book reviews here and there. I was a freelance editor at a TV recap site for awhile, which was fun and challenging since I didn’t actually own a TV at the time—oops! My turnaround time was lightning quick, I was super reliable, and they liked my voice and POV. I think that’s what got me noticed at HG. The EIC at the time brought me on as an editor to run the site and social platforms on weekends. I was also really hungry for work opportunities. Whenever there would be an open position at a publication for which I was freelancing, I’d email my editor saying, “Me! I’m interested!”
What was on your to-do list to accomplish when you first joined HelloGiggles?
I wanted to learn as much as I could from the leadership team at HG, as well as my co-workers. I worked with incredibly smart, innovative women who worked their asses off, and I felt like, if they could reach success with their brains and hustle, so could I. I was lucky my first full-time gig was at a startup—our roles were fluid, and if I wanted to tackle, say, an interview with an influencer, or the launch of a new column, I could. As associate editor, I managed all of our social platforms and played a key role in their massive growth, managed social partnerships, wrote and edited stories, and eventually split up my time doing social and writing during the day and editing in the evening. I became our makeshift night editor, which was intimidating but awesome, since I basically had the site to myself for like, four hours.
What is a typical day in the West Coast HG office like?
I’d wake up around 6:30 a.m. to try to catch up with the East Coast, working with our New York-based news editor to make sure we were covering all trending news and that those stories were being packaged in an HG way. The L.A. team logs on around 8 a.m. We’d work from home, assigning and editing timely stories, showing up at the office around 10 a.m. And then basically we’d be super-glued to our laptops until 5 p.m. A lot of coffee is involved, but we make sure to take brain breaks that involve a Spice Girls soundtrack and good office snacks.
I’ve noticed the website has really grown up over the years in terms of content. Would you agree?
It’s grown a lot—we used to not have vertical editors. The team would just grab stories, assigning them out or writing them based on what we thought our readers wanted. The freedom was great, but streamlining the process was necessary when the editorial team expanded. Now, each editor has their own beat, and our strategy is much more data-driven. We analyze story performance on a daily basis so that we can deliver content our audience wants—and that’s helped elevate the site, because our audience is smart and clearly comes to HG for a specific lens.
At HG, you went from associate editor to senior editor to editorial director. What are some of your biggest accomplishments you’ve made with each stepping stone onward and upward?
My path has been untraditionally accelerated, and that’s all thanks to my bosses who had faith in me, my abilities, and the vision I had for the site. With each role, I took on more responsibilities and absorbed as much information as I could. As associate editor, I worked closely with the editorial director and EIC. They really finessed my pieces and taught me the basics of reporting and how to come up with a compelling headline. Since I also managed our Facebook page, I had insight into what our audience actually engaged with, so when I pitched stories, I already had the numbers in mind and could generally predict whether the story would perform. As senior editor, I learned how to manage a team. In my last role as editorial director, I oversaw all departments: edit, social, and video. I knew editorial, and I knew social media, but video was alien to me. I had to quickly learn the ins and outs of this form of storytelling, and I think I succeeded. We’ve had some insanely high video view wins the last couple years, and that’s because HG’s video team is genius.
A couple of years ago, HG was acquired by Time Inc. (now Meredith). Did the transition change how the business operated?
We were given the resources to grow in a way we couldn’t as a startup. We moved to a bigger office. The editorial and video teams grew. We were given more tools to succeed and became part of a network of legacy brands. Time wanted us to thrive and do what we did best. On the flip side, we had less control. There were more ladders to climb in order to reach goals we had set for ourselves, which is pretty commonplace in any large organization.
What’s a HelloGiggles published piece you’re most proud of right now and why?
It’s so hard to choose because HG publishes such smart, meaningful content every day, but an essay that really stood out to me lately was this one from our franchise, The Blend (a space on our site that encourages writers who identify as mixed race to tell their stories). It’s called “The Day I Found Out I Wasn’t White” and it’s an extraordinary piece that left me breathless. I chose to include it in HelloGiggles mag because the story deserved more eyeballs on it.
As you mentioned, HG recently launched a print magazine. What was your involvement like with this initiative?
I put together the lineup, editing each story and assigning ones that I thought would make a good fit for our first issue. I signed off on every page, the stories and the design. I wanted it to reflect what HG is: A digital publication that values diverse storytelling, isn’t ashamed of obsessing over makeup or a cool dress, and encourages readers to tear out the pages of our “BFF section” that includes a period name generator. I won’t say more, because you should totally buy it for the full experience.
Dipping our toes in traditional print is important, since it’s a platform HG’s never experimented with before, and there’s so much value in storytelling you can hold in your hands. Even though it’s a print version of HelloGiggles, it still feels familiar—we’ll never be able to shake off our digital-first mindset. With the help of amazing print folks at Meredith, I learned so much about layout and design and the complex work that goes into all the pages—you want to make sure the magazine is aesthetically and tonally cohesive from cover to cover. For now, HG mag is available in select locations (Target, Walgreens, and Barnes & Noble) and was mailed as an insert to PEOPLE subscribers. The team hopes to put out more issues in the future, so be on the lookout!
At the time of this interview, you’re leaving HelloGiggles to head to First Media as their editor-in-chief. Congrats!
I know! I’m sad to be leaving HelloGiggles. It’s where I grew as a writer, editor, content strategist, and manager. Plus, the HG team is family to me. But I’m psyched to start my new role at First Media. I’ve got some cool things planned and it’s exciting to get to reach such a colossal audience. Stay tuned!
Finally, what would you recommend to someone who wants to break into editorial and stand out in the digital landscape?
Do the thing(s) that scare you. If you’re not scared, you’re not challenging yourself, and if you’re not challenging yourself, you’re going to grow stagnant in your job. Bring ideas to your boss without her asking you to, and let her know you’re excited to execute them if they seem like a good fit. Follow your editor crushes and see what their journeys were like. What did they do to get noticed? Did they moderate panels? Did they start a video series or something equally cool and groundbreaking? Make connections with fellow editors and writers, get your name out there, make friends. Networking is, by nature, awkward as hell, but it’s important. If you are suddenly given more responsibilities that feel out of your wheelhouse, try to take them on even if you’re worried you might fail. Chances are, you’ll succeed. Because you’re smart and capable and way mightier than you think.
Image credit: Dan Magro
Heather Taylor is a former entertainment writer turned brand mascot aficionado (and head writer) for Advertising Week’s Icon Blog. She been published on HelloGiggles, Brit + Co, The Drum, and BettyConfidential. Find her on Twitter @howveryheather.