Jill Layfield is co-founder and CEO of fashion startup Tamara Mellon. Together they’ve raised tens of millions of dollars to empower women with a new direct to consumer apparel brand.
I had the great opportunity to interview Jill on a recent episode of the Dealmakers podcast. We talked about the fun and challenges fashion startups, staying ahead of the competition, curating company culture, raising a Series C round, and the importance of storytelling.
What’s Your Story?
Layfield had a great opportunity to be born in San Jose, California. An environment that seems to make the impossible possible.
After spending time growing up in Austin, Jill returned to Cupertino for high school. Then it was onto Santa Clara University to study communications and journalism. Something she wishes she could go back and continue to learn, to become a better writer and storyteller for business.
It’s an invaluable skill for connecting with customers, your board, employees, and investors. Far more so than just being able to put together bullet points and slides for a PowerPoint. It’s the writing that compels results.
Determined to be self-sufficient as soon as possible, she paid her way through college by waiting tables at Birk’s in Santa Clara.
There she met the team from 8×8. They offered her an internship in their Silicon Valley voice over IP technology company. Then a full-time gig after university.
These connections led to her meeting Jim Clark (Netscape and Silicon Graphics), who recommended she joined a new company called Shutterfly. A small team of just around 50 people at the time.
Then falling in love with rock climbing and finding a husband, Jill made the big leap to go out to Park City, UT. She found a gig at a small eCommerce company in a ski resort. They ended up being BackCountry.
She stayed with them, growing the company from $20M to $500M and moving up to COO, President, and CEO and an acquisition.
It’s competitive out there. No business can just rest on their laurels today.
It’s something Jill Layfield quickly found out as CEO of BackCountry. They were doing great at attracting online traffic. The conversions just weren’t coming through. Then they were hit with one of the warmest and driest winters on record. Not a great scenario for a winter-weather dependent business.
Backcountry had also benefited from bringing an industry online. But, now Amazon and others were aggressively pursuing the category as well. Needless to say, there were night sweats and tough decisions to make.
Jill lead the company through three things:
- Differentiation: Finding what they could uniquely own in the market and delivering what matters most to the customer
- Telling New Stories: Bringing new customer and product stories to life in digital
- Overhauling the Team: Bringing in a whole new tech, product, marketing and management team to be the company they needed to be to win
Finding A Foothold In Fashion
As with most true entrepreneurs, there comes a time when the company hits a certain level of maturity where you just don’t feel the shoe fits anymore. Jill had already been CEO, so she couldn’t move somewhere else as a CMO, CTO, or CFO.
It was then NEA suggested she would be a good fit for an early-stage company. She met Mark at Jet and Gwyneth at Goop. Then she was introduced to Tamara Mellon, former co-founder of Jimmy Choo.
Tamara was on a mission to disrupt the luxury footwear industry. She needed tech and eCommerce, savvy co-founder. They met. They hit it off. Jill moved her family to LA so they could work together.
They set out to build a fast-growth brand that went direct to the consumer. They created a disruptive force that made shoes in the same Italian factories as Jimmy Choo, Manolo, and Louboutin, without the 6x markup for retailers. They broke the fashion calendar and deliver new product weekly instead of twice a year.
They discovered a big innovation opportunity on the backend of the business in an antiquated supply chain.
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