In conversation with

Kristen Naiman

Chief Creative Officer at The RealReal



How do you evolve aesthetically without creating waste? What’s the true value of our stuff? What’s healthy about surrounding yourself with beautiful things that speak to you? Kristen Naiman had been exploring these questions when she got the call about becoming Chief Creative Officer at luxury resale platform The RealReal. Manifestation? We think so.

As the former SVP of Concept, Strategy and Creative at Kate Spade, Kristen is a questioner, storyteller and world-builder by trade. If you saw the #missadventure series – the offbeat short films of Kate Spade women like Anna Faris and Zosia Mamet – you’re already familiar with her work. And you’ll be, like us, waiting to see what she does at The RealReal. Our co-founder Emily has had the privilege of many mind-opening conversations with Kristen. Their latest, on the cusp of her new role, Emily recorded to share with you all.

Question and Answer

Heritage brands often struggle to move with the times without losing their loyal customer base. You have worked with American heritage brands like Kate Spade and Gap, how do you keep them relevant?

The best brands stay themselves and move with the world. It’s like a person: you have to try not to get stuck in one era of your life. You have to keep growing and adapting to the times while becoming more and more yourself. It’s important to know your truth and rely on it to respond to the world.

So, how do you know when to play into the moment?

The job of a heritage brand is to play into the cultural moment through the lens of who they are. Think about it like a huge dinner party. Different voices will pop in and out of the conversation at different moments when they have something relevant to say. The job is to notice what people are saying, what is influencing the conversation and think: what do we uniquely have to say about this particular topic, this particular moment?

For Kate Spade, that was joy. Saying “okay, the world might be upside down, but we can find a moment of joy, something that helps somebody feel a little bit better. It’s not going to change the world and we’re not going to pretend the world isn’t where it’s at, but we can choose to meet the world in a way that is true to us. Joy was Kate Spade’s authentic way into this cultural moment. To offer an antidote.

What’s an example of a brand that has done this really well?

It’s so often cited but the Gucci transformation was truly interesting. Alessandro Michele took the cultural temperature along with aspects of Gucci and pushed them through this gender fluid, cultural and social mash-up. When it launched it felt true to Gucci and it was also totally unexpected. It articulated something happening in the world but that hadn’t been reflected by fashion yet. Back to the dinner party metaphor, it was like: wow, yes, listen to that guy, what they are saying feels true. The connection to Gucci’s heritage was not obvious but he used the heritage aspects of the brand- the GGs, the snake, the floral, the bamboo, the leathers, and created an of the moment take on the psychological proposition of the brand: Italian glamour.

“The job of a heritage brand is to play into the cultural moment through the lens of who they are. Think about it like a huge dinner party. Different voices will pop in and out of the conversation at different moments when they have something relevant to say. The job is to notice what people are saying, what is influencing the conversation and think: what do we uniquely have to say about this particular topic, this particular moment? ”

You’ve just left Kate Spade after many, many years and you’re going on to be Chief Creative Officer at The RealReal. When you’re starting to work on a new brand, how do you immerse yourself in their world?

I believe in listening to the people who are there and using the temporary perch, 30 feet back, to notice what is happening inside. When I first got to Kate Spade, they were using the tagline “live colourfully”. The campaigns were super colourful and over the top. Before I started I’d written in my notebook, along with a list of notes, that Live Colourfully should be about living in a brave, interesting way, not wearing a colourful dress. I was so sure I had some unique insight about what needed to change. But as soon as I started, I realised they all knew what needed to change too.

Your role isn’t to be smarter. People are smart. Or to change a brand. It’s to use your fresh eyes and temporary distance to help your partners find the most powerful expression of the thing they’ve created. It’s to ask, how can we help it be more itself? How can we crystallise it into something that is as clear to others as it is to us, and make it shine.

What makes a great creative leader?

Holding a steady vision and helping other people see it too. Seeing people’s superpowers and clearing the way for them to get to do that thing they do. My first CMO at Kate Spade, Mary Beech, who I did some of the best work of my career with, was incredible at two things I needed to support what I was doing – cascading a strategy and being sage about who to put in what rooms when. Throughout my career, I’ve seen that my ideas are only as good as my ability to have a partner who can use their strengths to lift my strengths. The way information flows, how to get everybody aligned, when to give people weigh-in and when to unilaterally say “we’re doing this and I know it’s a little scary, but trust us”. That is an art. Mary’s ability to do that made me and the people I led able to do what we were best at. We have to all do that for each other.

How do you balance aligning everyone versus pushing people to do more interesting work?

If everybody is comfortable, you’re probably not pushing hard enough. You need to get the team to the point that you trust each other enough to take risks together: we’re clear with each other, we’re aligned in our ultimate goal, and now we’re gonna hold hands and we’re gonna jump. It’s a combination of showing them they can trust you to be honest and admitting none of us ever really know how something will turn out. Getting everyone comfortable with the idea that giving something a best effort is always worth it and that is not necessarily the same as the effort always working out.

You’re moving to a role at The RealReal, so it’s less about buying more stuff and thinking more about passing things on. Did that align with how you were feeling personally?

When I got the call for the job – which I had wanted for a long time – I’d been working on a collection of essays about people in my life and an object that plays a part in our story. I was writing about objects – a sweater, a watch, a framed note, an ashtray – as a way of writing about life. It was a way for me to work out some of the questions I had over the last bunch of years. What is the true value of our stuff? What is healthy about surrounding yourself with beautiful things that speak to you personally? Things play a part in our experiences. Our stuff is a part of our story, not a signal of our means.

What appeals to me about The RealReal – beyond the simple fact that there is nothing more sustainable than keeping things in use – is that it offers a way to evolve aesthetically without creating waste. You might be done with a certain period of your life and as a result, something you’ve loved. And maybe that thing reminds you of that time, or that person, or that moment. You can love it for the memory or association and also no longer need it.  But that doesn’t mean the thing is no longer useful. And passing that thing on to somebody else, repairing it, reselling it, reusing it is a way to acknowledge that value is bigger than any one person’s needs.

The idea of selling stuff that people don’t need is always a fear. We want to get to a place where we are only working on brands that serve a real human need…

We live in a culture that tells us our value to society is as consumers. The more you consume the more you “have” the more valuable you are. And as people who work in the business of selling things we have a responsibility to change that. It’s not that we should all be doing aid work. No matter what you do, if each of us does what is true to us, it lifts whatever it is that we do. If we all did that everything would lift.

I made my career in fashion because I love style and the way that people use aesthetics to describe themselves and the world around them. It’s fun. It makes people happy.  I can participate in the fashion business by telling people that they don’t have enough. I can support the message that they always need more. Or I can say: no, more will not make you happier or your life better. But using style to express who you are, how you feel, how you see the world and people around you can enrich your life.

Even with the agency, we said no to two projects because of the ties to Qatar government and their LGBTQ beliefs. And if we did that type of project, yes, we'd get growth but you’d to keep doing the things to sustain it.

What you put into the world is what you create more of. People would’ve seen those projects and it would have attracted more of that kind of work. Maybe you’re not going to grow quite as fast doing only things that feel right for you, but you will grow a business doing work that is aligned with what you are all about. It’s easier said than done.

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