So You Want My Job? Pinterest's Celestine Maddy's journey from magazines to Pins

What did you want to be when you were growing up? Does your job now resemble that in any way?

I wanted to make magazines and be a publisher, although I didn’t know that was the name for it for quite some time. I drew on my walls as a kid. I created characters and stories, acted them out in my room. I made zines at Kinko’s when I was a teenager. I cobbled together comic books using collage materials and staples because I have zero talent for drawing.

My professional work echoes the themes found in those types of creative expressions: narrative, the creation of a world, the sharing of information and ideas, art.

How did you get your job? Tell us the full-length story?

I took an unconventional path. I didn’t go to college - I made it less than a semester, to be exact. I don’t recommend this. There are incredible advantages to college, gaining a network, taking advantage of vast learning opportunities, and really, just not being left on your own at 18. That’s still too young for many, me included. I wasn’t sure who I was or how to pay my bills, but traditional learning environments just didn’t seem to suit me, my restlessness, the way I learn best.

So, I did it the hard way. I worked in almost every industry available to a young woman, from restaurants (I rightfully got fired from iHop) to making a magazine and failing. I worked at High Times, wrote for cool-kid pubs like Vice. I did retail and video editing. I said no to nothing. I considered everything a resume builder. I will be forever thankful to David Hershkovits, co-founder of Paper, for giving me a shot at circulation director. But magazines were struggling, and I was living in NYC. I was barely getting by. I needed money. I got lucky when I landed a “trend hunting” freelance gig. That’s not quite a job anymore. At the time, it was tangential to advertising and allowed me to see enough of the business to know I wanted in. In advertising, my trends became campaigns, became sales, became communities.

I leveraged my writing skills and started Agency Spy, which is now owned by Adweek. Creating that brand connected me with serious heavy hitters, but more importantly, that experience of building an online audience and breaking category expectations were the exact reasons I got my first full-time advertising job at StrawberryFrog.

During my ad days, I got lucky and worked for Ilana Bryant and Jean Vaughn - two powerful women who taught me so much about strategy; its connection to culture, how to use your gut, as well as how to leverage the data to achieve business outcomes. Such incredible women. Incredible minds. They also gave me my first lessons on how to stand up against the tide of patriarchy. Without these two, I would certainly not be the leader I am today.

It was hard to be in advertising and be just a strategist. I also wanted to create. To do so, I quit my ad job and founded a magazine called Wilder. This time, I had a hit. It was a joyful time in my life and one I hope to get back to one day soon. Within a more wild environment, among the greenery and shade, is undoubtedly where I feel happiest. I hope to get back to working in those environments again.

But, advertising was good to me. It helped me to discover org design and big tech, which is where I found my stride. Tech is for me. It’s hard. It’s demanding. It’s a constant bet. I love it.

Ok, so what do you do? How would you explain your job to somebody outside of this space?

Here’s how I would explain my job: I am the global head of brand for Pinterest. My job is to express and explain our company, our products, and our community’s value to the world. I tell stories about Pinterest that drive user happiness and business results.

What do you love most about your job?

The duality of my role is incredibly satisfying. I get to make creative things like B2B magazines or consumer commercials while still driving ROI and business results. Day-to-day, I am focused on the short term (what’s happening right now in our culture or the brand needs) and the long-term. My team creates the chapters that make up a saga, an epic. It’s just fantastic.

How would someone entering the industry go about getting your job now? What would be their route?

I know very few people who took a straight route to becoming a brand marketer or a vice president of marketing. It’s always circuitous, which is fitting considering the diverse skill sets you need. It’s never clear cut. The most unusual people end up being CMO.

My advice is to start small. Pick a small brand where you have a direct impact on how it manifests itself and drive it. Get your hands dirty and build a brand from scratch. Understanding what it takes to start a brand will make every job after much more effortless. You become a practitioner rather than a steward. Embrace being a brand starter and not just a brand builder.

What advice would you offer to others entering the advertising industry, especially at this weird time?

Many countries and communities are having a moment of collectivism or reconsideration. We’re on the cusp of a global cultural renaissance and if you’re in advertising right now, my advice would be to poke your client to live up to the potential of the world. Forget about trying to get them to do good. Get them to be an agitator. To be the first. To rethink the assumptions around capitalism and expectations that are inherent in whatever vertical they’re in.

What would you say is the trait that best suits you for your role?

Empathy. The world is huge and complex, and no one person, identity, gender, nationality is at the center of it. Being able to see the world from someone else’s viewpoint is a must for marketers.

Who should those who want your job read or listen to?

I don’t think there is an easy answer here. There isn’t a should. Culture is huge. There’s so much to ingest and process.

Switch it up. I regularly change what I’m listening to and what I’m exploring in an attempt to stay out of the echo chambers that traditional media and digital technology have created for us. I ask friends what they’re into. I go down rabbit holes on Reddit to understand new ideas. I regularly sign up for random newsletters and Patreons. I have a dummy TikTok account that just follows random terms.

But, I can tell you what I am digging right now:

• The future: Jenna Wortham and Kimberly Drew’s Black Futures
• The rabbit hole: Cherie Hu’s Water and Music newsletter.
• The tech read: Charlie O’Donnell on VC complicity in like everything
• That good ol’ Industry stuff: Rachel Mercer’s Overthinkers. She gets it.
• Last thing I bought online (this morning!): Rhea
• For the fam: Leila Day and Hana Baba, The Stoop
• Thinking big and broad: For the wild podcast
• Rethinking the norms: The Alphabet and the Goddess as I’ve become quite interested in language reform

I’d love to know what everyone reading is following and the trends that excite you. Reach out to me on LinkedIn and tell me what you’re following and where you’re finding inspiration.

Last week we spoke to Maktuno Suit, chief transformation officer of Iris, to mark the launch of The Drum's Digital Transformation Festival.