In the Room with Alexandra Wilkis Wilson

The Room Podcast
4 min readMar 8, 2022
In the Room with Alexandra Wilkis Wilson

Happy International Women’s Day!

We’re delighted to be celebrating our 50th episode with a special powerhouse guest, Alexandra Wilkis Wilson. Alexandra is a three time founder having Co-Founded Gilt, GLAMSQUAD, and Clerisy. ​​Gilt is a popular luxury e-commerce platform disrupting the way luxury goods are sold with its flash sales model. GLAMSQUAD is a leading on-demand mobile beauty services company (think Uber-style for hair, makeup, and nail services). Today, Alexandra is the Co-Founder and Managing Partner of Clerisy, a $100 million growth equity fund based in Miami investing in consumer and tech companies.

In today’s episode, we discuss Gilt and their original drop model, what’s next for Miami’s tech scene, and omni-channel 3.0. Let’s open the door.

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This season of The Room Podcast is sponsored by our friends at Silicon Valley Bank and Cooley.

Key Theme 1: Gilt and the original drop model

Gilt’s flash sale model mimics the excitement of a New York city sample sale. Alexandra and the Gilt team created an online environment that produces the same customer behaviors you would see in a brick and mortar sale. Back in 2007 when Gilt was getting started, many consumers were not used to buying luxury items online. Today, it has become normalized to anxiously wait for sneaker drops or apparel launches online first. Gilt was one of the early platforms to cultivate hype at the hands of a scarcity model. One specific way for how Gilt did this was only allowing user’s items in their check-out cart to last for 10 minutes. After that, poof it was gone! Alexandra draws the parallels to the current hype over NFT drops, where you only have a short time frame to mint your moment before it’s snatched up. It’s safe to say AWW and the Gilt team were earlier adopters, if not the first, leveraging what is now a common e-commerce go-to-market strategy.

Key Theme 2: What’s next for Miami’s tech scene

Alexandra is a born and raised New Yorker with Cuban-roots, and a long-time fan of Miami. Over COVID, Alexandra’s family moved full time to Key Biscayne, in the broader Miami area. Not only is Miami a place close to Alexandra for personal reasons, but it’s also a booming and exciting city in the evolving tech ecosystem. Alexandra spoke to the evolution of the art-world as it’s made more room for technology innovation and especially been adopted by the crypto ecosystem. She’s seeing interesting people, companies, investors, and creators coming together in the city in a collaborative way. Inclusivity is what jumped out at us as Alexandra spoke about her experience in Miami, any question, idea, or invitation is met with enthusiasm and support today. Alexandra is bullish on the future for Miami tech!

“It’s so fun, and I feel like the tech scene here almost feels like summer camp. I’m not even joking. My kids find it hilarious that every day it feels like I come home and I’m like I made a new friend and they look at me like I didn’t know grownups made friends. And of course they do, and not only did I make a new friend, but I learned a new thing. There’s so many interesting people moving here too.”

Key Theme 3: Omni-channel 3.0

“Over the next five years omni-channel will also add on one extra dimension, which is the metaverse and that is exciting and perhaps terrifying, and the brands that really just dive in there and figure it out sooner rather than later, I think will really differentiate them.”

Traditionally, omni-channel has been a term popularly used in e-commerce to highlight the integration of store’s physical and digital supply chains. In many ways “omni” has come to fruition at an accelerated rate, thanks to COVID-19. McKinsey reports that in the pandemic, e-commerce consumption has lept 10 years into the future. Alexandra acknowledges the long-awaited adoption of omni-channel but highlighted her belief that this retail mantra will continue to evolve, into a third iteration. It will now encompass brick-and-mortar, traditional web-storefronts, and the metaverse. While this additional dimension of omni is in the early stages, Alexandra has long been an early adopter. We’re looking to her for unpacking omni-3.0 over the next five years!

Thank you so much to Alexandra for joining us in The Room! This special 50th episode also concludes our fifth season of The Room Podcast.

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