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Women at work: Maggie Winter, co-founder & CEO at AYR

Women at work: Maggie Winter, co-founder & CEO at AYR

Ever wonder what it’s like to walk a day in someone else’s shoes (or spend a day in someone else’s job, as the case may be)? Us too! In our “Women at work” series, we’re talking to some of the most accomplished women we know about how they got to where they are in their careers, what advice they’d give their younger selves, and any tips & tricks they’ve picked up along the way.

The basics
Name: Maggie Winter
Job: Co-Founder/CEO, AYR
Age: 33
College major: English with minors in Art History and Film

The nitty-gritty:
What was the original idea that led you to found AYR?
AYR stands for “all year round.” We wanted to create an alternative to mass-distributed fast fashion. Instead, we focus on creating pieces you’ll love season after season, year after year. Because we sell directly to the customer, we can be a lot sharper on our price and value than traditional brands.

What does your typical work day look like?
My favorite thing about my job is that there really is no such thing as a typical day. Every Monday morning, we have a founders’ breakfast. My co-founders and I discuss our goals, tackle challenges, and catch up on our respective parts of the business. It’s the best start to the week.

We do almost everything in-house. We’re teaching ourselves new skills all the time, so there’s a pretty steep learning curve. I work a little bit with everyone on the team, and even though we’re quite small (seven of us!) it’s the most talented group of people I’ve ever worked alongside. I divide my time pretty equally between creative projects (working on brand and product) and more analytical aspects of the business, like selling trends and inventory investment.

Product is my favorite thing. I love learning about what’s working and figuring out how to give the customer more of what she wants. My background is in merchandising, and I absolutely love working with our co-founder and Creative Director, Jac, to develop future seasons. Jac designs every stitch that we produce, so we spend a lot of time obsessing over beautiful textiles, the perfect fit, the right balance of assortment. When we introduce a new piece, it is the result of nine or ten months of work.

What’s been the best part of going from a larger, more established brand to a start up? What do you miss from being at a large company?
There’s a sliding scale of support and freedom, when you compare larger teams to smaller ones. I miss the support of a larger company with lots of infrastructure and bigger budgets. On the other hand, we have so much freedom. We can adapt very quickly, we can experiment and iterate at an unbelievable pace. We own our decision-making in a way that’s incredibly fulfilling. We will implement more support and structure as we scale, but I hope we never lose the momentum, curiosity, and hustle we have now.

After two and a half years in operation, what has been your biggest learning about running your own business?
Focus! There’s an impulse to want to do everything at once. I see the potential so clearly, and there are so many exciting opportunities offered to us. But we started this brand with a purpose, to deliver great product with great value, to make fewer things better. We will do all the things we dream of eventually, but we have to make smart decisions early on so we have a strong foundation for future expansion.

How do you think about differentiating AYR from larger competitors?
In truth, I think the fact that we’re small is one of our greatest advantages. We intuitively understand this new customer who’s emerged — she doesn’t define herself by traditional demographics. Instead, she aligns with a set of values. A lot of the brands we grew up with haven’t grown with us. Maybe they can’t, because they’re too large or too risk-averse. But we have an opportunity to create a smart, independent brand that reflects how women today actually dress, shop, and live.

What advice would you give your 25-year old self about navigating your own career?
Be curious. Make friends on different teams. Consider a situation from another role’s point of view. We’re often working toward the same thing, but from different perspectives. We have different jobs for a reason, and it’s the combination of all those viewpoints that makes magic happen.

Quick fire questions:
Who are 3 businesswomen you most admire?
Angela Ahrendts
Natalie Massanet
Kirsten Green

What’s your favorite piece from AYR this season?
That’s easy. I’m obsessed with The Collapse Jacket. It makes me feel like Gwyneth Paltrow in the 90’s. I have it in this gorgeous deep green, very Great Expectations.

How many pairs of jeans are in your closet?
Probably 25 or 30. Mostly AYR – The Skinny in Jet Black is my uniform – along with a few favorite vintage Levi’s I’ve found along the way.

Favorite non-AYR recent clothing purchase?
I got a pair of Pleats Please Issey Miyake pants that I love. They’re probably my favorite non-AYR item at the moment. They travel so well and pack down to nothing.

Top 5 favorite follows on Instagram?
@AYR (duh)…

What book are you currently reading?
Riding the Iron Rooster by Paul Theroux. I’m obsessed. I want to read every word he’s ever written. I like adventures.