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How I Became... Chief Content Officer of Who What Wear

BoF sits down with host and content creator Hillary Kerr, the co-founder of Clique Brands, Digiday’s Most Innovative Publisher in 2018, to hear her how she built her career and discuss her new careers advice podcast: 'Second Life'.
Chief Content Officer of Who What Wear, Hillary Kerr | Source: Courtesy
  • Sophie Soar

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NEW YORK, United States — Hillary Kerr's career in fashion began with a retail job at the Gap during high school — a role she continued throughout college as Kerr gained a BA in English Literature from the University of South California and an MA in Magazine Journalism at New York University, completing editorial internships in New York, Los Angeles, San Diego and Sydney along the way.

Two weeks after graduating from her MA in 2003, pursuing a career in journalism, Kerr became an associate features editor at Elle Magazine, where she "swiftly fell in love with fashion." After a few years of freelancing for publications including Elle, Teen Vogue, Maxim and Nylon, Kerr teamed up with Katherine Power to launch Clique Media Group, now Clique Brands, in 2006 — the parent company to fashion and style site, Who What Wear, along with other websites, a creative agency and a clothing line sold at Target. Clique Brands was named in Fast Company's Most Innovative Companies list in 2017 and as Digiday's Most Innovative Publisher in 2018.

At Clique, Kerr oversees all editorial content strategy across the group’s varying sites, alongside casting and hosting the weekly podcast “Second Life,” which highlights women who have successfully transitioned careers. Since its debut in February 2018, the podcast has featured guests including actor and singer Jennifer Lopez, actor Jessica Alba and jewellery designer Kendra Scott; has reached nearly 3 million episode downloads organically, with an average of 50,000 listens per episode; and featured on the iTunes top 10 careers podcast list.

Today, Clique launches its extension podcast, "Life Lessons with Hillary Kerr", which celebrates women who have advanced in their chosen field. Now, BoF sits down with the podcast’s creator and host to discover how she has done the same.

What is it that attracted you to working in fashion?

I was initially most interested in pop culture, which drew me to print magazines in the beginning of my career. I always enjoyed fashion from an artistic point of view, but I didn't really understand how it impacted our day-to-day until I started working at Elle Magazine, where I swiftly fell in love with fashion.

When I was growing up, my family thought it was a bit superficial to concern yourself with fashion. But through working in the industry, I realised, just like it’s important to be articulate with the way you express yourself through words, fashion communicates something about you before you even open your mouth.

Understanding how the content you create reaches people is hugely important because that's half of what we do.

I also worked at the Gap as my first paid job at 16, then on and off throughout college. I didn’t initially understand how much that job would play a role in my career, but it was great, formative training, especially with being friendly and approachable, which were two things that fashion was not in the 90s and early 2000s.

What would you attribute to getting your first job in fashion?

I completed five pretty intensive internships in the industry before getting my job at Elle. I spent 6 months full-time at Marie Claire in Sydney; I worked at InStyle magazine in Los Angeles and in their beauty department in New York; I spent a summer working for San Diego magazine; and another semester working for Harper's Bazaar in New York.

By the time I finished my MA programme, I not only had an MA in journalism but I was also published in San Diego magazine, I had been factchecking, I had worked in a beauty department — I had done all of these internships that were relevant. So, it was very clear to my bosses that I knew what I wanted to do. That focus and dedication made me an attractive hire.

What was the biggest lesson you learnt as a junior entering a career in fashion?

I think the most important thing I learnt was to say “yes” to everything. At one point, I had a monthly art column and I knew nothing about art. I was nervous about writing it, which I expressed to my editor-in-chief, but she said: “Most people don’t know anything about art, you don’t either, so I think you’d be great for this.”

It did however take me a long time to find my voice at the table. Every week, we had editorial meetings in which the features team would pitch ideas. For the longest time, I was simply too intimated to share my ideas — and there were numerous times when I shared an idea with a colleague and they would bring it up and receive wonderful feedback, which made me competitive and frustrated. It took me a while to learn that I didn’t need to be afraid of having the wrong idea. Once I started speaking up, editors helped me refine ideas and I realised, if I could just get over my own self-consciousness, it would lead to great things.

What do you enjoy about working in digital media today?

Even though having a daily deadline is an entirely different cadence than what I was used to with print, it is exciting. That immediacy was incredibly thrilling to me, the fact that we were working on this break-neck, daily deadline situation. While that grind definitely gets hard — I think I wrote every story for the first four years — I felt so connected to what we were creating and to our audience.

Having an entrepreneurial attitude is of paramount importance, so that's coming from a place of yes.

Podcasts are another digital form of storytelling, but in an intimate and personal way. It's an incredible experience, getting to basically sit in the room with me and Jennifer Lopez, (Allure founder) Linda Wells or, in our new series "Life Lessons", the celebrity stylist Karla Welch, and hearing them say, in their own voice, the highs and lows of their careers, what they've learned along the way, how they've taken those lessons and used them to find their most fulfilling work.

What core skills do you believe are necessary for success in your field?

In this day and age, you have to be data-oriented. You have to know your analytics and understand the science of journalism too. Understanding how the content you create reaches people is hugely important because that’s half of what we do. We work closely with our audience development and data teams so that we know how to best serve our audience.

So, when I see a resume that says, “wrote articles for TKTK magazine” and another resume that says, “wrote 37 pieces for that performed 150 to 200 percent over average benchmark, yielding X amount of page views, X amount of unique visitors, and X amount of social media lift,” I’m much more interested in the latter.

I also think having an entrepreneurial attitude is of paramount importance, so that’s coming from a place of yes, being a problem solver and resilient, going the extra mile. You can teach people how to be resourceful, but I appreciate it when people can apply that on their own. For example, if you can’t get confirmation on the price of a product because the New York PR office is closed, how else can you get that information? Can you call a store? Is there another corporate office? Anyone that has that sort of skill set is going to go far in this industry.

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