My Creative Career: Pamela Drucker Mann, global CRO at Condé Nast

Her brother is a reporter, “and a good one at that,” and there was always an understanding growing up that he was the studious one, diligent about school, and that she would lead a more athletic life. This scenario never took into account her passion for reading, her love of Judy Bloom and the Gothic horror of VC Andrews, whose Flowers in the Attic was a particular favorite.

Neither did it take into account her fierce creative side or her highly developed debating skills. “As my mom would say, I was good at arguing,” she laughs, “so I definitely wanted to be a writer.”

She ended up following in her sibling’s footsteps, going to college in New York to study journalism. “I thought I was going to be an anchorwoman. I either wanted to be a serious journalist or take over the Today Show – I wasn’t sure which one.”

It was storytelling and creativity that she was drawn to, even if she wasn’t sure how to quite articulate that yet. What she genuinely enjoyed was talking to people and turning it into something bigger.

At the time, she was also interested in art history, which she minored in, along with studying sociology. “I was also deeply studying the art of partying,” she laughs.

Throughout college, she worked as a waitress, which resulted in a fortuitous meeting with one of the editors of Sassy magazine, who asked her to be part of a focus group that, in turn, landed her an internship. The now-defunct publication was a teen title that ran for eight years and was seen as the ‘feminist counterpoint’ to rivals like Seventeen. Notable covers include the April 1992 issue with Kurt Cobain and Courtney Love in an embrace with the text ‘Ain’t love grand?’ and an August 1991 monochrome spread featuring Keanu Reeves and Alex Winter at the height of their ‘Bill and Ted’ fame.

The founding editor, Jane Pratt, was someone Drucker Mann looked up to. “She was a prolific woman of her time. It was the post-feminist movement, but it was still kind of like women fighting the power. It’s when flannel shirts and Doc Martens were all the rage and she had a successful voice. It resonated with angsty teens like me who didn’t know they were lesbians yet.”

She remembers how she oversaw the ‘Letter to the Editor’ page at Sassy and that a photograph of her from that era, backward baseball cap and all, recently resurfaced, much to the delight of her friends who laugh about how it is mind-boggling she hadn’t realized at the time she was gay.

The internship became a full-time job and she would go to college during the day and then work long hours at Sassy after. “I just looked forward to going to work so much. I remember interviewing Ben Affleck and Matt Damon before they were Ben Affleck and Matt Damon. I look back now and I’m like, ‘Holy shit, I got to meet all these cool people.’”

At the time, teen magazines were all the rage and Drucker Mann found herself at the one that was pushing culture forward. Many of the editors she worked with during those years went on to be big movie producers or to newsbrands such as the Washington Post. It was an exciting time to get into the media game.

Working her way up the media ladder, writing and editing, at 27 she became a senior editor at Weider Publication, which owned sports magazines such as Shape. “It was kind of an amazing opportunity because I got to meet my heroes, whether it was celebrities or athletes; all these people that I grew up watching. I was excited about having the opportunity to interview them, get to know them and then help to tell their story.”

As she progressed, it became apparent that she was spending more time editing other people’s words than writing her own. After hours of work on different articles, making them better, someone else would get the byline, which wasn’t the career she had envisioned.

But with her self-assuredness and creative edge, she was invited out to join the sales calls while at Weider. She would listen to them discuss the brands that she wrote for using uninspiring words like ‘CPM’ and says she thought to herself, “What are they saying?”

So, she began to take over the meetings and articulate what the brands were truly about. It felt organic and she enjoyed being out in the world speaking to clients. Her impact was being noticed and the sales manager for Jump magazine took her aside and questioned if she wanted to get into sales permanently.

“I was like, ‘Absolutely not,’ because I thought salespeople were the dumbest people I’d ever met in my life.”

That manager was leaving for Primedia, which had Seventeen magazine, among many others at that time, and wanted to give Drucker Mann a junior sales role if she followed her. “I was flattered, but it was a no,” she recalls – until she realized the salary was three times what she was making as a journalist.

“So, here’s the irony of this story: I decided to take the job. I did not tell anybody in my life, any of my friends. I was doing this totally closeted and I was also a closeted lesbian at this time.”

Her first foray into the hustle and bustle of sales confirmed that she was on the right path. Being a creative person, deep down she knew she had an artistic advantage over the suits but was scared of judgment from her writer and academic friends.

What would transpire would be two ‘coming out of the closet’ moments and, ultimately, everyone was supportive. “My friends were more shocked that I went to sales.”

In April 2005, Drucker Mann was recruited by Condé Nast to be the beauty director of sales at Jane. “I’ll never forget my interview; I wore this Bad Apple T-shirt. I thought it would be cool to wear that T-shirt and a blazer to my interview,” she remembers. “I still like to wear a statement T-shirt now and again; people know that about me.”

During those years, the office was located at 4 Times Square and Drucker Mann recalls just how immensely intimidating it all felt, but she made her mark. From Jane, she went to Glamour and, over the past 16 years, has worked her way up the ranks to now being the global chief revenue officer for the Condé Nast brand.

“I knew the person that was in my seat at that time and I cannot believe I’m that person now because I remember just being so afraid of them. If you saw her walking down the hall, you would run the other way.”

She likes to think that she carries herself a little bit more casually than the leaders of that time, she says and adds that her day-to-day is always completely different, which is just how she likes it. She also has a crazy travel calendar: two weeks in India followed by time spent in Europe in the coming months alone.

She describes Condé Nast as the “Magic Kingdom“ of creativity and a place where she’s met some of her forever best friends. And Anna Wintour? “She’s amazing, I love working with her. We have a tremendous partnership and it’s quite amazing as a woman to be able to work with another strong woman who knows what she wants but is ultimately also quite collaborative.”

Something that people might not expect from the Vogue editor-in-chief is her humor, says Drucker Mann. “She’s funny. She’s really funny, really sarcastic.” And, of course, she is impeccably dressed, as are most people who work across Condé Nast’s suite of publications. “Having fun within the world of fashion is just a big part of the zeitgeist here, so it doesn’t feel forced; it doesn’t feel like you have to dress a certain way every day. I think people kind of enjoy the freedom and expression of getting dressed.”

As someone who has had a decades-long career in media so far, Drucker Mann has tons of advice for up-and-coming creatives. The one thing she tells her kids, though, is to deliberately pursue their dreams. Never assume that people know what you want. She also stresses the importance of networking and mentors, the latter of which she credits for opening many closed doors for her.

“I would not have been in any of my jobs if it wasn’t for someone else taking a chance on me. I think people sometimes forget that you’re not doing anything alone.”

Ultimately, her philosophy is to be scrappy, savvy and self-starting.

Read our interview with McCann London’s Regan Warner.