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Jessica Dvorett, SVP of CaaStle on why there is no such thing as balance on a given day

“There is no such thing as balance on a given day”: When I had fewer responsibilities outside the office early in my career, I was able to devote as much time as I wanted to my job. I dedicated a lot of time and found great satisfaction in leaving the office without a To-Do list […]


“There is no such thing as balance on a given day”: When I had fewer responsibilities outside the office early in my career, I was able to devote as much time as I wanted to my job. I dedicated a lot of time and found great satisfaction in leaving the office without a To-Do list and a clean desk. However, once I had children, my time at home became more precious and I couldn’t dedicate as many hours to work as before. I struggled with how to meet the demands of a rigorous job and still make time to spend with my young son. I was chasing the concept of “work-life balance” and it completely eluded me. One day, the head of my team helped me reframe the topic of “work-life balance”. She guided me to think of balance in terms of my total life rather than a given day or week. Some days you can have amazing professional success and that means you might get home too late to see your kids. Other days you might delegate a task you would otherwise do yourself, so you can make it to an event at school. As long as you are achieving your goals in both areas across the days and weeks, you have balance.


I had the pleasure of interviewing Jessica Dvorett, SVP of CaaStle + General Manager of Gwynnie Bee. Jessica formulated and led Gwynnie Bee’s revolutionary move into size inclusivity, launching an unheard-of downward size expansion from 10–32 to 0–32 in an industry that typically starts with misses sizes and expands into plus. The size expansion falls in line with the company’s overarching mission — to provide unlimited clothing for all women. Gwynnie Bee is a size-inclusive subscription service that allows women to access an unlimited wardrobe in order to shop better, wear smarter, and rediscover the fun of fashion. Leading the Merchandising and Branding team at Gwynnie Bee, Jessica was initially drawn to Gwynnie Bee for its ambitious use of data and technology to disrupt the consumer experience in retail industry. Prior to joining Gwynnie Bee, Jessica was the Head of Global Merchandising at Cole Haan. Earlier in her career, Jessica led strategy, consumer insights, and analytics for the North America and Merchandising organizations at Coach, Inc. Jessica holds an MBA from Harvard Business School (where she was a Baker Scholar) and a BA in Economics Magna Cum Laude from Harvard College.


Thank you so much for doing this with us! What is your “backstory”?

By the time I graduated from Harvard Business School, I realized in part through professional experiences at Virgin Group and Apple, that I was passionate about working for brands that use creative innovation to drive culture and products that inspire their customers.

Later, I joined one of retail’s most powerful brands at the time: Coach. Over the course of my seven years there working in strategy and consumer insights, I learned about differing areas across the business, and built relationships with multiple cross-functional partners. In doing so, I developed a passion for merchandising and ultimately left when I had the opportunity to run Women’s Merchandising for Cole Haan.

Cole Haan had just been spun out of Nike and they were looking to reinvent their women’s line. It was a phenomenal opportunity to both drive a new strategy and own the accountability for its execution. I spent three years at Cole Haan before coming to Gwynnie Bee.

Why did you join your company?

I have always been interested in ingenuity and strategic innovation. My roles at Coach and Cole Haan provided me a front row seat to the challenges traditional retailers faced in being at the forefront of innovation given the volume of existing business they had to protect. I had also been following the evolution of “digitally native” retailers and fashion technology companies for some time.

This allowed me to get involved with accelerators like the Entrepreneurs Roundtable, New York Fashion Tech Lab and XRC. When I met the Senior Team at Gwynnie Bee, I was incredibly impressed by them personally as well as their goal to build a new model for apparel based on access rather than ownership. I ultimately joined the team because I was inspired by the vision for the company and excited about the chance to work for CEO & Co-Founder Christine Hunsicker.

What is it about the work you’re doing that’s disruptive?

At Gwynnie Bee we are trying to change the relationship women have with clothing by removing the connection between what you own and what you can wear. The sharing economy is growing, and the retail industry continues to evolve. Gwynnie Bee lives in the sweet spot where the two areas overlap. By offering women access to an unlimited closet for a fixed monthly fee, we let them experiment with pieces they might not ordinarily buy, and we enable fashion to be about the experience and not the expense.

In 2018, we expanded our size offering at Gwynnie Bee to sizes 0–32. This was a groundbreaking and exciting way to empower all women to experience fashion in a new way. While size inclusivity is a hot topic in fashion right now, many straight-sized brands are beginning to offer larger sizes. We’re shaking things up by approaching size inclusivity in the other way.

When we first launched, Gwynnie Bee served women size 10–32, who represent 80% of US Women. After hearing from more women who wanted access to our service, we expanded our size offering — and we only offering garments that are available across the size spectrum.

We all need a little help along the journey — who have been some of your mentors?

I have been very fortunate to have worked for phenomenal people at many stages of my career — particularly for women in senior leadership positions who are key role models as well. My mentors have ranged from direct managers and my managers’ bosses who took an interest in me to cross-functional partners with whom I built relationships.

The expertise passed on from my former managers and team leaders acted as critical part of my career development that allowed me the opportunity to take on more responsibility and prove that I could further my career.

I also believe in identifying cross-functional mentors who can help broaden your perspective in a way necessary to taking on roles with larger scope. For example, my work in Strategy allowed me to meet Jody Kuss, the Chief Merchant at Coach. She created projects that enabled me to apply my analytical skill set to core merchandising challenges and this immersion ultimately enabled my transition to a Merchandising role.

How are you going to shake things up next?

As a data driven company, we are learning more each week about what works for new members as well as our core, so we can identify opportunities to serve them best. This summer, Gwynnie Bee launched a retail industry-first: a voice-activated adventure unboxing experience with Alexa, allowing members to interact with and learn about Gwynnie Bee’s size-inclusive subscription service. Gwynnie Bee is pioneering the use of voice technology to extend interactions with members as they open their box and try on their selected styles in real time. In this new program, Alexa takes the member on a choose-your-own-adventure while opening a Gwynnie Bee box. The member, acting as the main character of the story, is taken on a journey that places her into unexpected, exciting, and entertaining situations. Each scenario illustrates how and where Gwynnie Bee clothing can be put to use — from the common every day to the most unpredictable

Can you share 3 of the best words of advice you’ve gotten along your journey? Please give a story or example for each.

I am truly lucky to have received useful advice from my mentors throughout my career:

“Just get on with it”: After starting my career in consulting, I developed the very valuable skill of being able to look at a problem from many angles and understand multiple ways to approach it. However, I could suffer from analysis paralysis. As I’ve grown throughout my career, I have realized the value of rigorous analysis as well as the notion that regardless of how much you’ve learned, you just have to make the best decision you can.

“Luck is where preparation meets opportunity”: I have a very clear memory of my conversation with an early mentor who shared this advice. As I have grown in my career, this advice has stuck with me and allowed me to increasingly appreciate the concept that careers are not linear.

When I start a new role, I never know where it will take me. If I focus on learning all that I can from my role, leadership and colleagues, the groundwork will enable me to make the most of new opportunities ahead of me.

“There is no such thing as balance on a given day”: When I had fewer responsibilities outside the office early in my career, I was able to devote as much time as I wanted to my job. I dedicated a lot of time and found great satisfaction in leaving the office without a To-Do list and a clean desk. However, once I had children, my time at home became more precious and I couldn’t dedicate as many hours to work as before. I struggled with how to meet the demands of a rigorous job and still make time to spend with my young son. I was chasing the concept of “work-life balance” and it completely eluded me. One day, the head of my team helped me reframe the topic of “work-life balance”. She guided me to think of balance in terms of my total life rather than a given day or week. Some days you can have amazing professional success and that means you might get home too late to see your kids. Other days you might delegate a task you would otherwise do yourself, so you can make it to an event at school. As long as you are achieving your goals in both areas across the days and weeks, you have balance.

What’s a book/podcast/talk that’s had a deep impact on your thinking? Share a story with us.

The Innovators’ Dilemma by Clay Christensen was a very influential book for me. The book examines the evolution of industries, and how frequently the companies that grow large and successful in one stage of that evolution often miss the changes that will lead to the next generation of successful competitors.

While analysts may declare the demise of traditional retail or that we are experiencing “the retail apocalypse,” I think this book is a great testament to how all industries evolve. Fashion and retail have been around for thousands of years — the question is not whether women will continue to consume clothing, but rather how and from whom they will consume clothing.

I joined Gwynnie Bee because I believe the company is innovating the retail industry in a way that traditional retailers with well-established processes have not been able to do on their own. Given this, we are poised to recognize and seize the opportunity to meet consumers where they are today.

Some of the biggest names in Business, VC funding, Sports, and Entertainment read this column. Is there a person in the world, or in the US whom you would love to have a private breakfast or lunch with, and why? He or she might see this. 🙂

There are so many people with whom I’d love to have the ability to share a meal. However, if I had to pick one person, I think it would be Tina Fey. I loved Bossy Pants and have always admired both her success and the relevance of the advice that she gives about it. Plus, I’m pretty sure it would be hysterically funny.

How can our readers follow you on social media?

Follow Gwynnie Bee on social as we continue to innovate the retail industry!

● Instagram: @GwynnieBee

● Facebook: @GwynnieBee

● Twitter: @GwynnieBee

This was very inspiring. Thank you so much for joining us!

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