Leadership development is essential for business success and elevating women in the workplace, but many retailers stop investing in training once employees reach a certain level, warns Jennifer DiPasquale, president and co-founder of Women in Retail Leadership Circle.

“At some point in your career, you get to a place where there’s no more training,” DiPasquale says. “You’re supposed to walk through this magical door of leadership, have all the answers, and know how to solve all the problems. And that’s just not the case.”

Founded 11 years ago, Women in Retail provides executive women in retail and brand leadership with networking opportunities through virtual and live events. In a conversation with Inside Retail’s Amie Larter for the Retail Untangled podcast, recorded during Shoptalk Las Vegas, DiPasquale emphasised the need for businesses to continue supporting leaders at all levels.

“Whether you are a manager making your way up or the CEO of a Fortune 500 company, you still need leadership development.”

Women, in particular, should advocate for their growth – attend events, find coaches, join leadership groups – and clearly communicate the business value of doing so with superiors.

“Explain [to your superiors] how those activities will help you further your career and be more valuable to the business. It is so important to invest in your employees.”

DiPasquale recalls an era when inspirational achievement was defined by individual success – what your title was, what you were making, how large the company was – but she believes times have changed. 

“It has morphed over time to, ‘Okay, you’re sitting in the seat that you’re in: How are we going to reach back and help those that are coming after us?’ ‘What are we going to put in place now that is going to help our future leaders?’ That movement and that momentum have become a point of inspiration. 

The need for flexibility

“It’s not about the individual anymore, particularly for women. It is about the collective, and what we are doing is building community.” 

So, too, companies have to be flexible. “You have working parents, and you have women who are wearing many hats. How can you be flexible to help them? There are all these fantastic women out there who are raising the next generation, and they need some flexibility in their time and work schedule to do it all and to have any kind of a balance.”

She stresses that companies that lean into this strategy will win because they will have more loyalty and buy-in from their employees. “And, they’re going to do kick ass work because they want to be there. They see that you’re meeting them where they are at the time in their life when they need it most.” 

Resilience and adaptability

In the current uncertain business environment, great leaders need to adopt resilience and adaptability, says DiPasquale. 

“They have a gazillion things coming at them, whether it’s economic challenges, trying to navigate tariffs, climate change and weather unpredictability, the geopolitical climate, are all at the forefront of everybody’s mind. Forecasting is really, really hard right now, and I think these leaders are in a position where they have to pivot and adapt to what is coming at them. 

“Every year, I feel like we say we’re in unprecedented times, then the calendar flips and everybody goes, my god, it’s another unprecedented time.”

The importance of community for women in leadership

Women in Retail was created to give leaders a safe, supportive space to share openly – and honestly. Careers aren’t linear, she explains. There are failures along the way and talking about that matters. 

Women are wearing many hats. “We’re not just business leaders. We’re parents, caregivers, pet owners, and volunteers. So when a leader can talk about their authentic journey, that’s where the magic happens. It gives permission for people coming up the ranks to see that journey and understand the challenges along the way.

“Women have to be their own change advocates. No one is coming to help us but ourselves. And that is why you’ve got to become part of a community. You’ve got to build your own network,” she continues. 

“Typically, women want to help other women, so the worst that is going to happen is they are going to say, I don’t have time at this moment, but here’s another great person that you might be able to connect with. You just have to continue to build your network, put yourself out there, and make it part of your job.” 

Diversity boosts the bottom line

She says multiple studies show that companies with diversity and gender parity at the board and C-suite levels have better bottom lines. “It is factual. Companies with greater gender diversity have a 48 per cent higher operating margin than companies without. It is imperative we keep working towards that.”

Some of the companies seeking to improve their diversity approach Women in Retail for referrals. “We have oodles of talent who are looking for these board roles, and we’ve worked with all kinds of organisations that are helping women get on boards because it is so impactful. If we persist down that path, by 2030, we can reach gender parity in board and C-suite positions. That’s kind of the North Star to keep at the forefront of your mind: It is possible,” she asserts.

“The changes that we’re going to make for women are not going to be made by an individual, but by the collective community, by raising their voice, highlighting and amplifying these leaders so that they have a platform and the leaders that are coming after them have a platform as well. It’s the collective movement and positioning forward.” 

• Listen to the podcast to hear DiPasquale discuss what makes a great leader, highlight some of the standout examples of women succeeding in retail careers … and explain why your network can be your net worth.