Jess Greenwood is VP of Content and Partnerships at R/GA, a full-service integrated advertising agency that recently won Cannes Lion Agency of the Year. Jess spent the start of her career at Contagious, a brand consultancy reporting on trends, insights and remarkable creativity. She built a solid reputation for being one of the most knowledgable commentators on the industry before making the leap agency-side and joining the ranks of R/GA in New York. She did a brief stint at Google before returning to R/GA where she has been ever since. She has an incredible perspective on what it takes to succeed, can speak 4 languages and often takes her shoes off when public speaking.
What did you want to be when you grew up?
Everything. An army doctor, a writer, a forensic pathologist, a marine biologist, a linguist, a voice actress, and for a good four years, an Italian. I’m not sure I’m any more focused now.
Who would you invite to your dream dinner party?
The kinds of people who are wonderful for four hours and then suddenly get bored and go home. Most of my favorite writers and designers fall into this category. Doris Lessing, Grace Coddington, David Byrne, Stephen Fry, and Kanye West. He might be crazy, but at least he’s trying to make art.
What single book had the greatest impact on you?
The Golden Notebook by Doris Lessing. It’s dense and weird and mesmerizing, and in many ways a precursor to the internet (written in 1962). It’s the story of one person’s identity, written in four different colored notebooks as four separate but interweaving narratives, which is exactly how we mediate ourselves through technology now. The narratives all come together in the Golden notebook at the end. We don’t have a modern equivalent for that coming together yet. Real life and digital life are still too fragmented.
When do you go to bed and when do you get up?
Late, and late. I’ve always been a night owl. Sometimes I think the single biggest change I could make to my life is to be in bed, just sometimes, before midnight.
What is your favorite time of the working week?
Thursday afternoon. The witching hour for creativity plus silliness.
Can you briefly explain your career path to date?
As erratic as my childhood aspirations. I was a teacher in France, then a music producer, then a writer, then a strategist (at Contagious), then I came agency side to R/GA, then I went to Google, then I came back to R/GA. I was lucky to have fallen in with Contagious Magazine when I was really young. It let me travel the world, meet a ton of fascinating people, and figure out how the industry works from the outside before taking the plunge to start making it for myself.
What is the biggest obstacle you’ve overcome, as it relates to your industry?
I’m not sure I’ve hit any major obstacles yet, which means there’s probably one in the post. I’ve had to learn on the job a lot and have been very lucky to be working with people patient enough and encouraging enough to leave me to figure it out. On my first day agency side, my boss told me to ‘get on with it, and come find me if you f*ck it up’. Exceptional advice for someone who loves a challenge. It worked, too.
I think this latitude is going to become an increasingly important part of the industry. I see a lot of hybrid thinkers coming in on the ground floor, who need a little while to figure out where they can be most useful and fulfilled.
What motivates you?
The promise of great work, the creative people I work with and a desire to keep pace with them.
What advice would you give to someone at the start of their career?
You don’t have to make your mind up yet. Try a few things on for size. Life is both long enough to allow for experiments, and too short to spend doing one thing. Kiss a few frogs.
Oh, and take your shoes off when you’re presenting. You can think more clearly when your feet are on the ground.
What do you consider your greatest achievement?
Moving abroad four times and learning three new languages. It makes me sad how little emphasis we place on foreign language learning. Speaking another language gives you an amazingly transferable set of skills: empathy, fearlessness and understanding of what words can do.
What do you believe has been the key to your success?
Still working on it. Through Contagious, I was very lucky to have a visible role very early on and a perspective on the industry that made me useful in a lot of different settings. Also the ability to learn quickly, absorb information from a lot of different angles and copy the best bits of everyone. If you’re a strategist working with a genius experience designer or technologist, look at how they think and solve problems. Even if you never learn to create a journey or write code, other people’s processes are always fascinating.
What is the most important lesson life has taught you?
In work: Smile, say hello to everyone, try to be a positive force (I’m not sure I’m 100% there, but it’s good to have something to aim for). Also, don’t be afraid to have an opinion and make it clear, if you’re in a meeting, that you’re there because you add value, in whatever way is most needed.
In life: A mentor once told me, in a very offhand way, that he never took his sense of self from what other people thought. I find that deeply admirable, as it motivates him to make decisions according to his own extremely high standards and nobody else’s.
What do you believe are the personality traits of great leaders?
A magic balance of vision and empathy. I think sometimes we confuse leadership with ‘ability to defend adequately the status quo’. It’s really rare to have the ability to both see the future and persuade other people to go there with you.
What do you believe is the secret to rising up to the top?
I’ll let you know when I get there! In all seriousness, the people I see doing well fall into one of two camps:
1. The perennially curious. People who move often and push hard.
2. The perennially loyal. People who stay with one company and grow and change within that company. So many CEOs and CMOs and CCOs are promoted from within.
Both these groups are talented – you can’t move up if you’re not – but depending on what kind of person you are, what mindset appeals to you, these are the paths that seem to lead to results.
Occasionally, you get combinations of both. I’m lucky to work in a company that over indexes on these people. Loyal people who bring outside knowledge in, who go away and come back, and who shape the company through their curiosity.
What's next?
Building up a new practice at R/GA! We’re trying to figure out ways to get brands closer to creative culture in a way that feels real, and not forced or awkward or icky. It’s a tough nut to crack, but a delicious one.
As told to Caroline Hugall at Buvette New York on Friday 17th Apri 2015.