Meet Jennifer DiPasquale, a seasoned B-to-B executive and trailblazer in the retail industry, with a robust career spanning over 20, president and co-founder of Women in Retail Leadership Circle (WIRLC), president and chief revenue officer of Total Retail, she won the esteemed Women in Publishing Award in the Entrepreneur category.
Who is Jennifer DiPasquale? Define yourself
First and foremost, I am a loving, dedicated mother and wife who has a demanding job but never loses sight of which family (home or work) takes priority. At home, I am lucky enough to be chasing after three amazing kiddos and their hectic schedules. At work, I am a driven, creative, passionate leader who loves to create new products and services that provide the most value for our members and community.
How were you as a kid?
I think I’ve always been a genuinely curious person. I want to understand what makes people tick and what drives great leaders. I am also a naturally social person. I listen closely, especially when people who are much smarter than me are speaking!
“I try to surround myself with the best talent internally and find great mentors externally to help me grow. I strive to be transparent, speak my mind, and do what’s right”
You hold a bachelor’s degree from Penn State University. What did you study and why?
I studied communications. Looking back, although I probably did not realize it at the time, that was a perfect fit for me. I started my career in radio, moved to television, and then on to media and live/virtual events, where I have found my home.
You are President and Co-Founder, Women in Retail Leadership Circle, publisher, and pioneer of the retail marketing world, you have worked with Total Retail (TR) and the Target Marketing Group for over 18 years. With experience in print, online, e-learning, and event media, you won the esteemed Women in Publishing Award in the Entrepreneur category. What´s the recipe for your success?
The secret is there’s no one exact path to success — it is an individual journey. I think no matter how you define it; it takes grit and continual problem solving along the way. I think it’s also important to surround yourself with an amazing team that has strengths you may lack. I think a big part of how I define success is making sure we’re secure for the long run and executing on our mission — to champion women upward in their companies and give them a solid foundational community to rely on during their professional and personal journeys. Perhaps the biggest measurement of success this year is that I didn’t have to lay off a single teammate, and I know a lot of leaders can’t say that. And for that, I am truly grateful.
You launched the Women in Retail Leadership Circle, an exclusive community of women executives at leading retailers and brands, where this idea came from? And how have the results been?
We founded Women in Retail Leadership Circle and Summit, our marquee event, in 2014 to fill a void in the retail industry and serve needs that these executive women were simply not getting. Years ago, when we started to look at the numbers, there were not nearly enough women on boards or in executive seats at enterprise retailers and brands. We have created a platform and community designed to champion women forward. In truth, it was profitable from Day 1, which I know is unusual for a startup. That speaks to the need in the market. And it’s been growing steadily ever since. I’m proud to say we’ve 10x’d in five years, so clearly, we’ve hit a nerve and are serving a need. It also means there’s so much room for expansion and we have so much more work to do.
“I don’t think you can ever underestimate the importance of active listening. We’re constantly listening to our community of women leaders to see what will help them most in their roles and how we can create useful content for them”
We know there are a lot retail events in the USA, you organize Women in Retail Leadership Summit, what makes it unique?
I think what is unique is our content mix of retail strategy and leadership development. The event provides a place where executives can connect in person and then through the Circle (the association itself). They can connect year-round. Each year we offer a mix of content around retail trends and strategy, including highlighting leaders in the space, as well as executive professional development. That seems to be the magic combination for us. The content is private — we do not even cover it as press. We want to have a safe space for the speakers to feel comfortable sharing their wins as well as their challenges. The women who speak are super authentic and willing to share not only their successes, but their challenges as well and what they have learned along the way. When we launched, I was really blown away to see how transparent, honest, and even vulnerable these executives were about sharing their personal experiences. To me, that does not exist elsewhere; it’s unique to this environment.
Do you have any philosophy that guides your career decisions?
I am a demanding but fair leader. I try to surround myself with the best talent internally and find great mentors externally to help me grow. I strive to be transparent, speak my mind, and do what’s right (even if it’s not the consensus). I am always a big proponent of continuous learning and growth, and I’m always looking for white space. When launching new product lines, I consider how can I launch something that is meaningful, educational and long-standing for both retailers and partners/vendors?
“I am continually networking and learning. You need to follow key leaders within your own industry as well as outside of it to have a well-rounded vision”
What is the biggest the lesson you have learned over the years in your career?
The biggest lesson I have learned is to pay it forward. Our community is built on helping women succeed and thrive. If I can make a helpful introduction for a job opportunity, make a referral, offer career or business advise, etc., I am happy to do it. It is all about paying it forward. And the good karma does not hurt either!
What does a normal workday look like for you?
A normal workday consists of getting the kids ready for school, hopefully successfully and in good moods! I typically check LinkedIn and media channels for pertinent news, etc. And then it usually is a series of nonstop meetings and action items post-meetings. Right now, of course, they’re all on Zoom, but they typically would be in person or on the road. It’s typically a mix of team meetings and partner meetings.
What do you love most about your job? & what is the most difficult part?
What I love most is being able to engage with other female executives and getting a close-up view of their leadership strategies in action. I feel so honored to be able to call them colleagues and friends. I truly believe in what we are doing, and that the women that we serve are so inspirational. The most challenging part is always resourcing and time management. We have more ideas than we do time to execute on all of them and resources to do so. I think that is true for most companies these days.
“I think you CAN have everything, but maybe not all at once. I think there are seasons of life when family becomes a priority and seasons of life when your job and career are a priority”
What is one strategy that has helped you to grow your business?
I don’t think you can ever underestimate the importance of active listening. We’re constantly listening to our community of women leaders to see what will help them most in their roles and how we can create useful content for them. We are forever tweaking our events and content based on audience feedback. We want all the feedback — good, bad, and ugly — so we can consistently improve and adapt. I need to believe in the products we créate, and won’t push anything to market I do not believe in. If we help our partners grow, so will we. I have lived by that mantra my entire career.
As an entrepreneur, what is the one thing you do over and over and recommend everyone else does?
I am continually networking and learning. You need to follow key leaders within your own industry as well as outside of it to have a well-rounded vision. I’m in a constant state of learning, whether it be from networking with other leaders, listening to podcasts, taking classes, reading books, conducting research, etc. There is a wealth of resources at your fingertips.
What are the do and don’ts in female leadership?
- Do network, always.
- Do continually step outside of your comfort zone.
- Do lead by example.
- Do know your strengths and limits.
- Do not avoid conflict and leave things unresolved.
- Do not discount others’ perspectives.
- Do not pretend to have all the answers.
“Seek out anyone who inspires you and ask for mentorship, whether it is in your own industry or not”
Everybody has had dark moments in their lives, what have you done to get out of that phase?
I think everyone has dark days and even dark seasons. It’s part of life. I think you have to surround yourself with the energy you want to ultimately receive. It takes work to build positivity and pull yourself out of dark times. And even if you’re in a good place, it still takes work to maintain that positive space. I think it helps to consume the kind of content that is valuable to you in the moment. Do you need motivational content? Meditation and reflection? A pep talk from a friend? You must surround yourself with the right people and consume content that lights your heart on fire.
What do you like to do in your spare time?
I don’t know if I know what “spare time” is! I am married and have three kids, two sons ages 15 and 13, and a daughter who is 9. So, they keep me busy (and laughing!) every day. I do try and exercise every other day and read as much as I can. I love podcasts, too. I am always consuming professional development podcasts.
Many authors say women can and must strive to have everything – a shining career, a blossoming family life and a perfectly balanced lifestyle all at once, others point out that– then women are placing unrealistic expectations on themselves if they believe they can have it all, you have 3 kids and you are married, so according to your experience, what do you think about these statements?
I think you CAN have everything, but maybe not all at once. I think there are seasons of life when family becomes a priority and seasons of life when your job and career are a priority. Sometimes it’s even day by day! I am constantly seeking the right balance, as most women juggling various aspects of business and personal lives tend to do.
What are your plans for the future?
We’re embarking on the launch of Women Leading Travel & Hospitality in January 2021. The travel and hospitality industry has been severely affected by the COVID-19 pandemic, but it’s also one of the most important industries of the future. We’re building a community of supportive executive women who will ultimately rebuild and reshape the travel industry. https://womenleadingtravelandhospitality.com/
There is still the glass ceiling for women in the world: Fewer opportunities, jobs underpaid just for that fact of being a woman, etc. Have you experimented with the glass ceiling? If yes, what are the biggest challenges you have faced and how have you overcome them?
I think part of the solution is to know your market value, and then ask for it regardless of gender, race, etc. If you are truly not being paid what you deserve, then it’s time to move on. If you’re in an organization that isn’t reflective of the diversity you’d like to see at the top, it may also be time to move on.
What tips, can you give to young girls who want to work in the retail industry like you?
Seek out anyone who inspires you and ask for mentorship, whether it is in your own industry or not. Just ask for a virtual coffee. Some will accept and some won’t, but you will need a network of women to help support you along the way no matter what industry you are in.
I think in your position, many people may have the wrong idea of who you are, and what do you (professionally), with this idea in mind, what is being Jennifer, and what´s not?
I think the term that springs to mind is a “balancing act.” I think myself, like most females, are consistently trying to juggle careers, family life, friends, personal wellness and professional growth and development. There are seasons of life for each, some seasons are for your family and some are more for your career trajectory. And I think I am always seeking the right balance in my life on a day to day and season to season basis. I do not have it all together every day, no one can. I am forever trying to create the perfect balance.
Who is the woman you admire the most and why?
I admire SO many women — too many to list! Sara Blakely of Spanx, Mary Dillon of Ulta, Angela Ahrendts, and a laundry list of so many more. I admire women who have built businesses from the ground up and have earned great respect from their teams. I love leaders that have grit and tenacity and who can inspire others.
Name: Jennifer DiPasquale
Sector: Retail, Travel & Hospitality
Company: Women in Retail Leadership Circle and Total Retail
Designation: President and Co-Founder