When hiking Mount Kilimanjaro (casual), Samantha Dong injured her toes — and changed her life forever. After sustaining an injury, she realized she couldn't bear to wear her favorite shoes: her workday high heels. She started to wonder why heels couldn't be more comfortable — not just for the injured, but for everyday women. Then, Ally Shoes was born. Dong's company produces pain-free heels for today's power women. 

Dong would know a thing or two about being a power woman. She started her footwear business with no experience in the field; She credits her success to her management consultant experience, agility and the driven women who make up the Ally Shoes team. 

We spoke to Dong about her career and how she managed to launch a company in a cut-throat industry she'd never stepped foot in. We learned about her path to success — and a thing or two a day in her shoes. 

Fairygodboss of the Week: Samantha Dong

Founder and CEO, Ally Shoes

New York, NY

Tell us a little about your career. How did you get to where you are now?

I started my career as a management consultant. It was the best first job because it exposed me to various industries and business units. My strategy role taught me to learn how entire businesses and industries work in a very short period of time. Then, I joined a 15-person tech start up in San Francisco called OrderAhead, which was acquired by Square. I started out in operations and product management but assumed many different business roles in the company. Wearing many different hats, I perfected being nimble and creative to deliver results quickly with limited resources. 

After a few years in the workforce, I went to Stanford’s Graduate School of Business. During my MBA, I climbed Mount Kilimanjaro and injured my toes. That was a life-changing moment for me because heels have always been part of my work uniform. After that hiking injury, I couldn’t bear the pain of wearing my heels even though I wanted to. That’s when I started to ask myself: Why do heels have to hurt in the first place? I watched comfort become a major trend in sneakers and flats and decided that it’s about time we bring that trend to high heels. So, a little over a year ago, I started Ally Shoes — pain-free heels for power women on the move.

What is an accomplishment that you are proud of?

Founding Ally Shoes has been the most rewarding professional accomplishment of my life. To build a brand for women by women that addresses an important fashion need gives our team great pride. As a brand, Ally is reimagining how fashion supports and empowers women every day, and we’re just getting started. Since launching our online store last year, we’ve received overwhelmingly positive feedback from our customers and have been featured in top fashion outlets. This year, we’re accelerating our growth with new product launches, including our first-ever bridal line.

What is a challenge that you've faced and overcome?

It hasn’t been easy starting Ally Shoes with no experience in footwear and aiming to solve a problem that has existed in women’s shoes for so long. It was actually helpful that I didn’t come from the footwear industry, because it empowered me to ask the obvious questions, challenge the status quo and push to figure out how to make heels fit better.

Who is YOUR Fairygodboss? and Why?

I couldn’t build this brand alone and it wasn’t easy to assemble the right team — but we did. I partnered with two leading women experts in the space: Dr. Roxann Clarke, a podiatric surgeon, and Sara Jaramillo, an accomplished footwear designer. We involved real women every step of the way, from designing to sampling to real-life wear tests. With their feedback and support, we successfully re-engineered the statement heel with long-lasting comfort. Overcoming the challenges led to our innovative, patent-pending design.

I’m fortunate to have a lot of Fairygodbosses in my life. I would love to acknowledge Anu Penmentcha as a powerful influence on my career. We met when she showcased some omnichannel strategy projects for retail clients. She quickly took me under her wing when I expressed my interest in the area, and looped me in on client projects, relevant white papers and events. She has been an advocate and mentor for me every step of the way, from business school applications to giving me sound advice when launching Ally. 

What do you do when you're not working?

I love yoga, reading, hiking, puzzles and making and drinking tea.

If you could have dinner with one famous person - dead or alive - who would it be?

Michelle Obama.

Lightning Round: What is your karaoke song?

"Any Man of Mine" by Shania Twain.

Lightning Round: What is your favorite movie?

"The Shawshank Redemption."

Lightning Round: What book would you bring with you on a desert island?

"A Global History" by L.S. Stavrianos.

Lightning Round: What is your shopping vice? What would you buy if you won the lottery?

I love shopping for shoes (obviously). I also have a weakness for tea sets. If I won the lottery, I would buy a house.

What is the #1 career tip you'd like to share with other women who want to have successful careers like you? 

I would advise you to take calculated risks. You should always take on roles that give you the capacity to learn and the opportunity to learn from the best people. It’s vital to surround yourself with a strong and supportive team.

Why do you love where you work?

I love the process of creating something new and useful that benefits a lot of people. It’s a joy to lead a mission-driven brand and to experience customer reactions when they first step into our shoes. Our customers are real women who love heels and style but also appreciate comfort. They inspire us as they take on the world and stride through life in our shoes.  Ally is never just about the shoes. We want to be the brand that represents the qualities of a modern woman — beautiful, strong and uncompromising.

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