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Employee Spotlight: How Stephanie Bentley’s Fashion Background brought her to True Fit

From personal shopper to digital fit expert, Stephanie Bentley tells us why she joined True Fit and how she utilizes her fashion background to help brands grow digitally.

From personal shopper to digital fit expert, Stephanie Bentley tells us why she joined True Fit and how she utilizes her fashion background to help brands grow digitally.

Stephanie Bentley is a digital fit expert on True Fit’s account team. She has brought ten years of unique industry experience to True Fit, working for brands like Lafayette 148 New York, 11 Honoré and Adam Lippes.

We recently sat down with Stephanie to discuss her impact at True Fit, the challenges in ecommerce retail in 2023, her mission to connect fashion with shoppers and what most excites her about being part of True Fit's dynamic team.


Can you explain your role at True Fit?

I am an Account Executive and was brought on to start building out our offering with mid-market brands. I am responsible for driving new business by educating retailers and brands on the impact and value True Fit can bring to their business.

What is something that has surprised you as you get deeper into your role at True Fit?

Learning about the history of how we built our connected dataset has surprised and impressed me. Our size recommendations are produced from the connection between 82 million active shoppers and hundreds of retailers.

Having a best-in-class product behind me makes me proud to represent True Fit in market.  As I’m researching customers, I can see the potential and the gap in their PDP experience and provide recommendations for how to leverage AI to grow conversion, impact traffic and drive ecommerce return reduction

Tell us about your background in fashion. What drew you to True Fit?

I was on a plane to New York City two days after graduating from college just knowing I wanted to be in the fashion industry. I did not know what realm of the industry I wanted to be in but I knew fashion was where I belonged.

I landed in sales, and I think it was the best thing that ever happened to me because I love helping people. I started my career at a small women's boutique retailer doing sales and marketing. From there, I transitioned into personal shopping at Lafayette 148 New York. I did that for five years, dressing women from 0 Petite to 24W. I helped women across a very broad range of sizes and it was extremely challenging at times but that is what also made it so rewarding.


"While personal shopping at Lafayette 148 New York, I dressed women from size 0 petite to 24W. I helped women across a very broad range of sizes and it was extremely challenging but that is what also made it so rewarding."



I think sizing and fit is in my blood, and I love to help people figure out what fits them, and what makes them feel good. A great fitting garment can really create a long term connection with a consumer because it can be so challenging and overwhelming to find what flatters different body shapes and preferences. Working directly with shoppers to steer them toward a wardrobe that suits them was a great FIT for me. My New York fashion chapter continued with my work at two other womenswear companies and where I helped to build out their direct to consumer businesses. 

Once Covid hit, I decided I wanted to take my fashion and retail experience and move into the tech space where I could help retailers leverage technology to expand their brand and business. I worked for a payments company called Verifone where I sold payment solutions to enterprise customers - from retail to hospitality. I loved helping retailers but ultimately I was looking to marry my fashion background with technology, and in doing my research, I decided that my background in fit and ecommerce experience could really lend itself to what True Fit solves for both brands and consumers so I reached out for an informational interview and said, “I really want to work here!”

When the position for Account Executive was posted, I reached out right away. It was a wonderful interview process and I’m excited to be here!

What do you think is the biggest challenge retailers and brands are facing today?

It is an interesting time in the market and it is quite challenging to build consumer confidence and turn new traffic into loyal customers.  In the mid market, it is all about relationship building, whether I am connecting with the founder of the brand or the head of ecommerce. It has been important to show them what long term value and impact we can bring to their business.

Every brand is different and faces unique challenges so it has been important to listen to their needs to match our platform's capabilities to their business challenges. 

Returns have long been a hot topic in retail, particularly for sized goods like apparel and footwear. With your experience both in stores and with digital technology, what are your thoughts on how brands can solution around retail returns?

Ecommerce returns are inevitable and businesses are always strategizing on how to reduce returns. I have seen a shift in returns as a shopper. Many brands are adding a return fee to their offer or selling final sale merchandise. There is a strong desire to solve for returns but brands also want to make the customer happy and get them into the right merchandise for them.  

True Fit is creating seamless experiences for shoppers and by doing that, we are helping retailers build quality relationships with high value shoppers. It is that moment of confidence for that customer to think, “I love this item, I know this brand has great quality, and I know it's going to fit me perfectly.” True Fit is removing the shopper hesitation, building loyalty, and lifting conversion for brands.

What excites you most about what lies ahead for you and your True Fit team?

The number one thing that excites me is that I'm making shopping fun for the consumers. And in return, I am helping to improve the major challenges the mid-market faces. I genuinely like when the customer is so excited when they receive their item and say, “Thank goodness it fits, it's awesome!”. I am so excited to build a trusted and consultative relationship with these mid market brands.  Knowing it will form a stronger bond between the consumer and the brand is the icing on the cake.

Fun Facts, Getting To Know Stephanie:

When was the first time you used True Fit?

Five years ago.

What is your favorite technology product from the past five years?

I'm going to have to say the new iphone. I realize it's kind of a lifeline now.

What is your favorite footwear brand? 


What was the last clothing item you purchased online? Did it fit you?

I purchased a denim blouse by Made in Tomboy, and it did fit me. And because of that, it is my go-to top!

How would you characterize your personal style in one word?

Probably French with a tomboy twist.

Favorite Season of Clothing?

Fall, I love outerwear. The outfit becomes more interesting with layers and accessories, and it is more fun.

What retailer do you want True Fit to partner with the most?

My favorite denim brand is AGOLDE, but I would say in general, any kind of up and coming contemporary brand.