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Hi, fintech fam! 💜

On Saturday, I had the privilege of speaking at the 34th Annual Women in Business Conference hosted by the Harvard Business School Women’s Association.

I’ve always believed growth happens through content, community, and connection. Hearing powerhouse speakers share their journeys and strategies for success just reinforced everything we’re building at Fintech Is Femme.

We stand on business. And nothing beats the power of community-sharing tactics that work. That’s precisely the value we’re bringing to the table at the Fintech Is Femme Leadership Summit.

There’s nothing more powerful than learning from the women who’ve paved the way.

Their blueprints for success—especially in areas like longevity, sustainability, and consistency—mirror our work at Fintech Is Femme.

That’s the vision for our Leadership Summit, coming up on April 23 during NY Fintech Week. Trust me, you won’t want to miss it. Grab your tickets here.

Now, let’s dive into today’s column.

INNOVATION

Two Tech Trailblazers Share Blueprints for Success in Entrepreneurship and the C-Suite

When navigating the upper echelons of entrepreneurship and the C-suite, Jennifer Hyman and Amy Weaver have become trailblazers. 

One leads a billion-dollar fashion disruptor; the other transforms how sales and finance meet technology. 

If you’re wondering how to scale your company, develop an authentic leadership style, and navigate adversity, look no further than Hyman and Weaver. 

These two women share the playbook—no secrets, just raw truths—from their keynote interviews at the 34th Annual Women in Business Conference, hosted by the Harvard Business School Women’s Association.

I had the honor of speaking on a panel myself, but I made sure to arrive early to catch some of the other sessions. And let me tell you—their leadership tactics resonated with me the most.

Jennifer Hyman, CEO of Rent the Runway, founded the company that revolutionized how women think about fashion and rental services. 

When Hyman and her co-founder launched Rent the Runway, neither had experience in fashion, tech, or logistics. 

In fact, they didn’t have a formal business plan in place—they just dove in.

 As she recalls, “We didn’t think we needed a strategy. We just needed action. You don’t know what will work until you start, so we jumped in and figured it out along the way.” 

She quickly learned that success isn’t about the idea—it’s about execution. 

For Hyman, it’s all about pace. 

“How quickly can you learn? 

How fast can you innovate and get your product to market? 

And most importantly, how humble are you to pivot when things don’t go as planned?”

For Hyman, what makes a business successful isn’t just having a big idea, but the ability to constantly adapt and iterate. 

“We were acting fast, without any money, without any experience. We made mistakes, but we learned. And that pace of learning and innovating is what convinced Bain to invest.”

But no one could have predicted what would happen next.

Pandemic Hits Hard, Yet Her Belief Stays Strong

When the pandemic hit, Rent the Runway’s business went from skyrocketing to nearly zero. 

“People weren’t buying clothes anymore. They were living in pajamas,” she remembers. “It was a huge blow.” 

But even as the company faced its most challenging year, Hyman knew that rental fashion was here to stay. The timing was just too right. It’s a similar intuition that guided her to build Rent the Runway in the first place. 

“I had this gut feeling that the behavior of renting clothes was already in people’s lives, whether they realized it or not,” she said. “We borrow from friends, we rent vacation clothes—we’re already doing it.”

With Instagram pushing the notion of curating personal brands, Hyman saw a market on the brink of change. But back in 2008, there was no proof that Rent the Runway would work. It was just a belief in her vision—and in timing.

Looking back, Hyman’s confidence in the company’s future hasn’t wavered.

 “The fact that today millions of women rent clothes, buy secondhand clothes, and the whole ‘sharing economy’ has exploded—this was exactly what I envisioned 15 years ago.” 

Yet, the road to success hasn’t been easy. 

“There were days when I thought we might not make it, but now, 15 years in, I’m more passionate than ever about what we’re doing.”

Despite the pandemic’s hit to revenue and the countless hurdles Rent the Runway has faced, Hyman has stayed resilient. 

“I’ve seen our company go from peak to valley, but our mission hasn’t changed. I believe rental fashion is a core part of the closet of the future, and we’re building that future.”

IPO: A Historic Moment

One of the most historic moments of Hyman’s career came when Rent the Runway went public. 

She learned she was the 30th woman in history to IPO her business—and the first to do so with an all-female leadership team. 

“It was a surreal moment. My family, my team, our board—it felt like everyone who helped build Rent the Runway was there celebrating.

We were able to raise the capital we needed to stabilize the business post-COVID and set the stage for the next chapter. The IPO was truly one of the most special days of my life.”

However, the joy of the IPO quickly collided with a harsh reality: the stock price plummeted. 

“We had to raise debt to survive COVID, and a week after our IPO, the market crashed. Our valuation dropped from $2 billion to $600 million,” she said. 

That’s the reality of the market.

But even as the company’s financial standing took a hit, Hyman remained focused on the long-term vision. 

“What I realized is that when the financial world has forgotten about you, you focus on doing the right things for your customers. And that’s exactly what we’ve been doing. We’ve been transforming everything.”

Leadership: Building the Right Team

When Hyman reflects on the company’s success, she credits her team’s commitment to Rent the Runway’s vision. 

“The most important quality I look for in someone is belief,” she shared. “You can teach skills, but you can’t teach passion. And negativity? That’s the last thing you need.” 

Instead, hire the people who inspire others, lift the team, and can see the potential in others that they don’t yet see in themselves.

Hyman knows you can weather any storm when you have the right people. 

“It’s about surrounding yourself with those who are just as passionate and committed as you. They’ll push you to keep going, and you’ll do the same for them. That’s the secret to a great team—and a great company.”

Sales: The Ultimate Skill

As she’s learned through her journey, sales is one of the most essential skills to master. 

“Whether you’re convincing someone to work for you, to join your team, or even to marry you—sales is everywhere. It’s about understanding people, building relationships, and inspiring those around you. I can’t stress it enough—sales is the foundation of success.”

For Hyman, it all comes down to loving what you do.

“I’m privileged that three-quarters of my board has been with me for over 13 years. Half of my executive team has been here for over 12 years. We’ve built something incredible together. And even though the business has faced setbacks, I’m more committed to Rent the Runway than ever.”

Ultimately, Hyman believes that a passion for what you do can carry you through even the most challenging times. 

“The glory fades, the money doesn’t matter as much, but when you love the work, your team, and have a bigger vision—everything else falls into place.”

Amy Weaver: The Unlikely CFO Who Embraces Risk and Redefines Leadership

When Amy Weaver stepped into the CFO role at Salesforce, she was anything but the typical candidate. 

Having previously served as the company’s Chief Legal Officer, she was, by her own admission, “not qualified” for the role. 

But, in a moment of candid conversation with a colleague, that lack of qualification turned into an empowering challenge. 

“You’re right,” her colleague said, “You’re not qualified to do the CFO role we have right now.”

A wonderful CFO who was very traditional filled the role.

“But that’s not what I’m looking for. I want someone who can be a strategic partner and help set out the financial strategy for the company. I want you to take the role and make it yours.”

It was advice that would change everything for Weaver. “It suddenly took away all of the comparisons about why I couldn’t do it, or why I didn’t fit, or why I didn’t have the skills,” she said. 

“It made me realize that whatever the job was, I needed to grab it and make it my own.”

And that’s exactly what she did. The role of CFO in the 21st century has evolved beyond its traditional financial duties, and Weaver’s transition from legal to financial leadership exemplifies that shift. 

As she put it, “CFOs now are strategic partners, and the role has changed more than any other in the C-suite.” 

Her legal background, which might have been seen as a non-traditional path to the role, gave her a fresh perspective and allowed her to bring a unique blend of strategic thinking and legal expertise to Salesforce’s financial operations.

Take Risks, Embrace Terrifying Opportunities

Throughout her career, Amy has leaned into discomfort and fear. One piece of advice she gives to the next generation of women rising in their careers is simple but powerful: 

“You’ve got to lean in. You’ve got to take risks, do terrifying things.” 

But she acknowledges that it’s easier to give advice than to follow it herself.

“I realized it’s a lot easier to tell other people to do that than to do it yourself,” she confessed. “And I thought about coming back to my college or my law school, and I asked myself, ‘What kind of credibility do I have to tell you to take those risks if I walked away from what was the biggest opportunity, just because I was scared?’”

In the end, Weaver jumped in, taking on the role four years ago, and has since had an “incredible experience.” 

Her journey is a testament to the power of embracing risks that scare you.

The Unexpected Challenge

Investor relations was one of the toughest aspects of Weaver’s transition into the CFO role. Being a woman in a traditionally male-dominated space, she navigated challenges she hadn’t encountered before.

“I had walked into a lot of jobs in my life where I was the only woman, and lots where I was the youngest in the room. But I never walked into a role where people fundamentally questioned, ‘Could I do it?’” she recalled.

Her first earnings call was a humbling experience, as she wasn’t asked a single question and wasn’t even acknowledged. 

“I felt very alone,” Weaver said. “It was humiliating, but also a moment that pushed me to prove myself.” 

In the following months, she dedicated herself to building credibility and learning the ropes, eventually turning that difficult moment into a success. When it came time for Salesforce’s investor day, she was ready. 

“I was on stage for an hour, taking questions and leading the conversation. One of our top analysts, who had initially criticized my appointment, sent me an email afterward that simply said, ‘Pitch perfect.’”

Leading with Kindness

Weaver is also a passionate advocate for a leadership style that may seem counterintuitive to some: 

Leading with kindness. 

Her belief in this approach was solidified after an experience with a young woman at a previous company. Despite being incredibly smart and skilled at her job, this woman was frequently underestimated because of her soft-spoken, polite demeanor. 

“People confuse kindness with weakness,” Weaver explained. “And not only is that dead wrong, but in her case, it was her greatest strength. She got me to do more things than anyone else, simply because she was kind.”

Weaver has been vocal about her commitment to kindness in leadership, even facing criticism for it in a male-dominated space. 

“When I gave a graduation speech a few years ago, I spoke about kindness as the most important leadership trait. 

Some people came up to me afterward and said it was ‘brave.’ It made me realize that they thought kindness was soft—and that it took courage to embrace it, especially as a woman.” 

For Weaver, however, kindness isn’t a weakness; it’s an essential strength that inspires loyalty and respect.

What’s Ahead?

Looking back at her 11-year tenure as CFO of Salesforce, Weaver is proud of the legacy she’s built, but she’s equally excited for the next phase. 

“I have some exciting things ahead of me, but I can’t talk about them just yet,” she teased. While her exact next steps remain a mystery, one thing is clear: Amy Weaver is not one to shy away from a new challenge, and she’ll continue to redefine leadership in whatever role she steps into next.

Weaver has proven that leadership is not about fitting a mold—it’s about breaking it, taking risks, and owning your journey. In doing so, she’s become a trailblazer, showing that sometimes, the most unconventional paths lead to the most extraordinary successes.

Learning from women like Jennifer and Amy is exactly what we’re doing at the Fintech Is Femme Leadership Summit on April 23. 

This summit will bring together bold leaders, innovators, and entrepreneurs to share their stories, strategies, and lessons. 

It’s an opportunity to hear firsthand from leaders who’ve carved their own paths, proving that leadership is not a one-size-fits-all formula. See you there.

_{WTF ELSE?}

• Argentina’s $4.6 billion crypto scandal, largest-ever crypto theft

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• Fintech Brex eyes $500 million in 2025 revenue as IPO is mulled

• Crypto trading volumes reportedly reached $18 trillion last year

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• 📰 Today’s Read: Last week, I wrote a profile on Congresswoman Maxine Waters, exploring how we can all embody her inspiring Auntie Maxine energy. Check it out here.

• 🍿 Today’s Food: Enjoyed a coffee and a very good Lox bagel at a charming spot in Boston known as Pavement Coffeehouse.

• 🌍 Today’s Watch: Loving this Big Think video, which offers a refreshing perspective on why being “on top of everything” is an unrealistic goal in work and productivity.

• 🎤 Today’s Event: Adding a special event to kick off Women’s History Month next week at Brex HQ. I’m hosting. Join us by RSVP here.

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That’s all for now! See you Thursday!

Love,

Nicole 💜