Ally Shoes’ CEO & Founder Samantha Dong shares a powerful story of male allyship, women’s leadership and effective product design.

I am passionate about empowering women to be their best selves through fashion, making luxury footwear more accessible for women on the move.  Our brand, Ally Shoes designs pain-free heels for power women.

Our own Ally story illustrates the amazing outcomes that come from diverse, female-led teams, while showing how men can play an important role in developing a revolutionary product for women. It’s a powerful story of empathy, product design, inclusion, and allyship.

The Beginning

I was never an insider to the retail or fashion industries. I started my career in management consulting, and later moved into tech. As a consultant, I had always considered heels a welcome part of my work uniform. I was aware that a few extra inches somehow elevated my presence and confidence in a very emotional and personal way. I always considered myself a shoe person, as I’m sure a lot of women do.

Therefore it may not be a surprise to read how I regularly put up with whatever pain came from my heels. Often that pain included pinched toes accompanied by the daily inconveniences of changing heels in the bathroom after arriving at my office from a pavement-heavy commute.

Shortly before I started studying at Stanford Business School, I trekked Mt. Kilimanjaro with friends for 7 days. I came down with severe tendon injuries in both of my feet, which took me awhile to recover from. I found myself unable to wear heels.

I tried shoe inserts, comfort brands and nothing looked quite right on me.  I realized that I would need to decide whether or not to wear stylish shoes and suffer or wear comfortable shoes and compromise the confidence and fulfillment I had come to appreciate in my heels.

Neither option seemed right to me.  We are in an era where women are told that we can “do everything and have it all,” but the simplicity of combining style and comfort had not yet made it to my own modern lifestyle.  There had to be a better way.

Vision and Prototype

At Stanford, I decided I would test ideas for a better heel for women. I decided to take a shoemaking class and I shadowed shoemakers every time I went back to my home country of Shanghai. I wanted to learn the craft directly from them.

My first prototype was, in fact, a pair of heels from a shoemaker in Shanghai.  I sent an email to all the women in my class and said, “If you want a pair of heels that are comfortable, Venmo me and I’ll get a pair made for you.”  I sold about 20 pairs that way, and it’s when I realized my research validated my hunch. Women needed comfortable, stylish heels that were better than what was currently offered.  I decided to raise capital and dedicate my time to developing this product.

Meeting Jeff

When I moved to New York to pursue my idea full-time, I knew I now needed experts to help me. 

I started looking for seasoned veterans in the industry, who had worked for brands I respected, and were experts in areas such as design and engineering.  

Number one on my “wish list” was Jeff Henderson.

Jeff has a background in mechanical engineering and industrial design. He worked at Nike for 20 years and later as Innovation Director of Cole Haan. He had everything I was looking for, including starting his own creative and product design agency in NYC.

I didn’t think he would meet with me and there was no way I could afford him – but I reached out anyway. He responded and we met at a restaurant on the Lower East Side.  

I told him about my idea and what I wanted to do. I admitted that I wasn’t sure  how to do it, that I need help and shared that I couldn’t afford him. I asked if he would help me and he said ‘yes’.

Jeff’s Support… And Our Woman-Led Team

As I look back on that first meeting with Jeff, I realize it was a similar to other big moments where people have taken a chance on me. Whether Jeff, my early adopters, or the early investors who gave us capital, they all believed in my vision.

I told Jeff that I really wanted to have a woman-led team.

I was surprised by how male-dominated the industry was. Almost all of the shoemakers I encountered, plus the majority of designers, were men.  I had developed my own prototype and vision through a deep understanding of the customer experience, which was so vital to developing the right product.  

I knew that male designers simply hadn’t walked in women’s high heels and therefore couldn’t understand the literal pain a woman endures. But it was just my hypothesis at the time, and I mentioned this to Jeff.

A few weeks later, Jeff said, “There is someone I want you to meet.”

He introduced me to Dr. Roxann Clarke, an accomplished female podiatric surgeon. Dr. Clarke had treated many women on Wall Street – her practice was situated in Manhattan’s financial district. Often by the time women came to see her, it was too late for surgery.  As luck had it, Dr. Clarke had been looking to get into shoemaking. We met at a diner in Manhattan and she became my first business partner.

Jeff also told me I needed a good designer, and he knew a woman designer would be so important to our product.  He introduced me to Sara Jaramillo, who had worked on the Adidas collaboration with him. Sara had been an industry veteran who was willing and excited to work with me on a shoe that could be both beautiful and comfortable.  

And that was our original founding team: Roxann, Sara and me.

Jeff, who had introduced us all, was our coach.

The Power of Inclusive Design

Having a diverse industry skillset as a female leadership team (Roxann, a podiatric surgeon, Sara, a designer, and me from Silicon Valley) encouraged us to deeply look at the woman’s experience and what she needed in a shoe. Our team hosted many afternoon salons and events, where we heard from women directly about their pain points and what they would like in their heels.  

This empathy for women’s experiences remains a critical way we design for our female customers, and proved important when we launched our first nude line of shoes. Immediately following the successful launch of our black heels, in both suede and leather, we knew we needed to expand. Naturally, the next color would be nude.

Roxann, Sara and I looked at each other and said, “What exactly is a shade of nude?”  

Roxann is African-American, Sara is Latina and I am Asian.  So when it came to nude shades, we knew we needed at least 3 – and decided to do 5.

It was risky at the time; but that’s what having a diverse team, and being an outsider to the industry offered me. Nude in fashion had always been one shade of beige, and I trusted there was likely a business reason for that. We wanted to do what was right by our customers. 

Lessons from Jeff … and the Industry

I’ve said it a few times, but it bears repeating that I have learned a lot as an “outsider” in this industry.  

Jeff mentioned early on that he appreciated I didn’t come as an insider, because I have a fresh perspective – almost a naivete – about how to realize my vision. This enabled me to push boundaries. He will say things like, “Do you want to try a new material?” or “Do you want to test out something that has never been done before?” and usually I will say, “Yes!”. I know I have a strong team of experts who can help realize a seemingly-crazy idea in the most effective way.

As a male ally, Jeff took a chance on me but that’s why his support was so instrumental. He is a male ally who was willing to share his knowledge and network with me. His belief in my vision has been the catalyst for our all-women leadership team coming together to create a product that truly impacts and empowers women.

On Becoming Ally Shoes

It took us a long time to get to the name Ally, but once we did, it made a lot of sense.  We want to be part of a woman’s every day life and a part of her big moments.

We hear from women every day – with photos and stories about how they wear their Ally heels. It is a wedding shoe. It’s also a power heel for when women go to conferences, present on stage or argue cases in court. Ally shoes are trusted comfort on a date night or spending time with loved ones.

It’s been incredible to see how this one little product can have so much impact on someone’s life.  We cherish the feedback we get from customers because it helps us continuously improve. 

That’s the core of our work at Ally. What unites our entire team is we all want to do something meaningful for women’s empowerment, and meaningful in general. We are all creators, and we take joy from creating something useful for people.

– Samantha Dong, Founder and CEO, Ally Shoes, New York, NY
Visit Ally Shoes: www.ally.nyc