Jennifer Hyman, founder and CEO of Rent the Runway, reflects the lessons she learned in the first 15 years of building and leading her company.
US fashion-tech company Rent the Runway was founded in 2009 and pioneered the ‘closet in the cloud’ by renting out designer clothes at affordable prices.
Under the leadership of Jennifer Hyman, the company has been named in CNBC’s Disruptor 50 list five times in 10 years, and has been placed on Fast Company’s Most Innovative Companies list four times.
In 2019, 10 years after the company was first founded, it opened a software and technology office in Galway – its first office outside the US – creating 150 jobs in the process.
Here, Hyman discusses the lessons she has learned through her 15 years of running the fashion-tech company and shares her advice for other leaders and founders.
Don’t stop believing
15 years ago, I co-founded Rent the Runway as a 27-year-old business school student with a bold vision to revolutionise the way women engage with fashion.
Over the years, I have led the company through exhilarating highs, such as being the first company to go public with a female founder/CEO, COO and CFO (a distinction I am extremely proud of) and crushing lows, including the dramatic impact of Covid-19 on the business. But my steadfast belief in the company’s mission has kept me going through it all.
Ask yourself regularly “Do I still believe?”. It’s this question that matters the most. Belief in your vision is the fuel that powers innovation, resilience, and reinvention.
Trust your instincts
In 2009, there was no data suggesting that within 15 years, millions of women would regularly rent clothing. Back then, women didn’t rent clothes and designers didn’t engage with the second-hand market.
Yet, I believed rental would become mainstream and I believed that because I trusted my instincts. As Rent the Runway grew and we gained access to vast amounts of data, I often felt pressured to prioritise data over intuition when shaping our strategy.
That was a mistake. True innovation for us couldn’t come from historical data because, by definition, we were creating something entirely new. When your instincts clash with the numbers, lean into your gut. Have faith in your ability to see a vision that data cannot yet quantify.
Speed is everything
Even the smartest ideas fail more than half the time. That’s why speed matters more than perfection. At Rent the Runway, our greatest successes have come when cross-functional teams are empowered to pursue goals, build their own roadmaps, and launch new ideas every week.
Yet, as organisations grow, agility often gets replaced by bureaucracy. Strip away processes, meetings and even metrics that don’t directly drive value. Everything you do should focus on increasing the speed of execution.
Stay in the game
The person who plays the game the longest wins. It doesn’t matter who wants to take you out of the game, keep on moving and keep on playing. If you stick around, you’ll be successful.
Continuous learning, continuous humility
You’re going to make a million mistakes; there’s no avoiding that. The objective should be to see how quickly you can recognise those mistakes, learn from them and make the changes needed.
For me, it’s been a decade and a half of bobbing and weaving, making some mistakes and figuring out how to grow from there.
Re-hire yourself
Every few years, I challenge myself to approach my role at Rent the Runway as if I’m stepping in as a brand-new CEO. Fresh leadership naturally questions the status quo and pushes for change.
After 15 years at Rent the Runway, I know every metric and decision inside out and this familiarity helps ensure we stay true to our vision. But it also poses a risk: the tendency to stop asking “Why?” Why are we still doing this and why haven’t we fixed that pain point yet?
This year, I treated my role as if I was just starting out. The result was one of the boldest growth and innovation strategies we’ve ever pursued. By the end of 2024, our 15th in business, I’m incredibly proud of all that the team has achieved and how deeply Rent the Runway resonates with our customers and community.
By Jennifer Hyman
Jennifer Hyman is the founder and CEO of fashion tech company, Rent the Runway.
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