Episode 27: Investing in women leaders: Why ongoing development is non-negotiable

From Shoptalk Las Vegas, Amie sits down with Jennifer DiPasquale, president and co-founder of Women in Retail Leadership Circle. They discuss the need for businesses to continue supporting leaders at all levels and how companies that lean into this strategy will have more loyalty and buy-in from their employees.

Transcript

Amie:

Welcome to Retail Untangled. My name is Amie Larter and this is the podcast where we speak to retail industry experts and find out business hacks that help them succeed. You won’t find these gems anywhere else, and we have some superb stories from the coalface as well as helicopter insights from retail industry leaders.

It’s not often you get to see Times Square taken over by 25 inspirational women in business and retail, but that’s exactly what happened earlier this month, when the Women in Retail Leadership Circle, alongside The Z Suite, The DealmakeHers and the Retail Influencer Network announced the 2025 Most Inspirational Women Leaders. Today, I am joined by Jennifer DiPasquale, the president and cofounder of Women in Retail Leadership Circle to discuss these influential women, their impact on retail and her advice for the next generation of leaders. 

There's some amazing leaders on this list who work at or own phenomenal brands and businesses. So can you start by letting us know what are some of the most common characteristics you've observed among these powerful women?

Jennifer:

Yeah, for sure. So that was such a fun list. So we put that together with the fabulous Stacey Burns and the Dealmakers. And we also launched our own top women in retail list this month as well. So we're trying to take advantage of the Women's History Month and amplify and highlight all of these fabulous leaders. back to your question of characteristics, I mean, we just talked about it. The only constant is change, right?

So I would say, you know when you look at any great leader that's running and navigating these businesses as such, resilience and adaptability is key, right? They have a gazillion things coming at them, whether it's economic challenges and, you know, trying to navigate the tariffs or, you know, climate change and weather unpredictability, geopolitical climate, you know, is at the forefront of everybody's mind. So forecasting is really, really hard right now and I think these leaders are you know in a position where they have to pivot and adapt to what is coming at them and it seems to you know every every year I feel like we say we're in unprecedented times well then the calendar flips and everybody goes my god it's another unprecedented time.

Amie:

And here we are again.

Jennifer:

Exactly so I think you know really the resilience and adaptability is just key for all of their, their leadership.

Amie:

Yeah, no, I can imagine. so there's one list and then there's the more retail specific list. So can you give me some two examples of, you know, tell me the stories or stand out examples of women who are really challenging the status quo and pushing boundaries in retail?

Jennifer:

Yeah, I mean my gosh they are and whether they're on these lists or not we have so many, I mean every leader has a story right their own personal journey is pushing the boundary okay whether. 

Amie:

I know and we've heard so much in the last couple of days about storytelling.

Jennifer:

Yes. 

Amie:

It's so true. 

Jennifer:

I mean, they are every leader that steps on our stage and we've had, you know, some phenomenal ones. You know, I'm thinking of Jamie Kern Lima, who is the founder of It Cosmetics and, you know, sold her billion dollar brand. And she, you know, she got on stage and just told her personal journey of just failure after again and again and again. And, you know, how do you, you know, keep that mental mindset strong if you believe in your business and you know that you can push forward. I mean she's an incredible just story you know in and of herself. 

I mean you think of we've had Indra Nooey on our stage you know former CEO of PepsiCo and she just talked she just you know, talked about her vulnerability, you know, and just her how she poured into her people and her team. Just again, in unprecedented times and really changed the culture of that company. You look at Claudia Cividino, she's the head of Jared and on the list of Signet Jewelers. And she had the privilege of having her on our stage and she stepped on stage and, the best leaders that you can see are on stage and they're telling the vulnerable side. 

You people don't want the shiny new version of, my career was linear and by the way, I was able to have a family and everything's rosy and the business rose from the minute I stepped in the door and just off we went. That's not the real deal. It is freaking hard, right? And you zigzag on your path and there are failures and it's okay to talk about that.

And by the way, women are wearing all of these other hats, right? We're not just, you know, leaders in business, but we're, you know, raising generations. We're caring for parents. We're pet owners. We're volunteers. We're wearing all the hats, right? So I think when a leader can, you know, really talk about their authentic journey, that's where kind of the magic happens. And it opens and gives permission for, you know, people coming up the ranks to see that journey and really understand the challenges along the way. And it's okay to talk about.

Amie:

I love your platform and the fact that you've got this platform for just sharing these amazing authentic stories. 

Jennifer:

Exactly.

Amie:

Because without it, people don't, you don't see yourself. You don't need to hear these perfect narratives. It's very much about seeing yourself, seeing someone, you know, drive change, do really well, know that it wasn't easy. It didn't come easy.

Jennifer:

It's exactly it. And we, you know, there are conferences for that, right? Like we're at one right now at Shop Talk. I mean, you get on the stage and you talk about the business strategy and there are places to do that. We wanted to create at Women in Retail an opportunity for these leaders to talk about their holistic leadership, right? And not just the business side of what they do, but, you know, everything else that pours into their full leadership.

Amie:

And I love that because it goes back to the why, yours is obviously talking to that point and you know, everyone has a different why and the space for different kinds of stories, but I just love that you're the why for the women in retail leadership circle is really to bring those voices to life and have those conversations because it's it's the way to make change, isn't it? 

Jennifer:

It is. 

Amie:

It is,  OK, so looking at the list, we see people from diverse backgrounds representing different parts of the industry, often serving overlooked consumer demographics or groups. How do you define inspirational? Because if we're talking to inspirational. I'm sure the definitions changed over the last, you know, four years particularly since you guys have started 11 years ago.

Jennifer:

Yeah, I think this is such an interesting question. I think inspiration, you know, once upon a time was, the individual achievement, right? You know, what your title was and what you were making, how large the company was and kind of, you know, the original roadmap of what we saw as success. And I think it's 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, right? 

What are we going to put in place now that is going to help our future leaders? And I think that that movement and that momentum has really become, you know, a point of inspiration. You know, I also think and you and I have chatted about this, it's not about the individual anymore, you know particularly for women. OK, it is about the collective, you know, and that's what we're doing is really building community. 

You know, these changes that we're going to make for women, it's not going to be by an individual, it's going to be the collective community, you know, raising their voice, giving them a platform, highlighting and amplifying these leaders so that they have a platform and the leaders that are coming after them have a platform as well. So it's the collective, you know, movement and positioning forward. 

Amie:

Yeah and have you seen and I'm keen to get your perspective on this because I'm obviously seeing this over time as well. Have you seen there, it's not that there's a hesitance but has there been struggles getting that collective momentum? 

Jennifer:

You know, it's funny, we, so we're 11 years old, right? This is before, you know, DE and I even was, you know, a phrase in this space. When we launched, it was so interesting because we were doing work and events in the retail industry. And we, you know, women naturally congregate together. And so we kind of went to the women and said, hey, we have this idea bubbling in our head, you know, we want to put together a community that is retail strategy and executive leadership development. Where are you getting that on the female side of things for women? And they were like, OK, that doesn't exist. You even know what you're saying, right? And so honestly, we put together a board of retailers. And it took off from the minute that we had zero idea what we were doing. 

We were in the event space but in terms of membership and in terms of building a community for women, we were just kind of winging it. And the board has really helped us to, we say every year and we iterate on it every year. Okay, what do you need now in this moment? Right? 

Amie:

I love that.

Jennifer:

Coming out of COVID, it was, hey, we need some wellness. We need to pour into our own cups. We were a little mentally frazzled, right? So we poured into the wellness side of it. Now it's okay, hey, we're trying to get to the economic challenges that we're dealing with and those headwinds coming out. So we're leaning more into the business strategy side of it for them. So truthfully, I feel like when you give people the community and you build it and you allow them to be part of that, you know, path forward and what they want, it just kind of, you know, becomes a movement in and of itself.

Amie:

And I think you guys have done such a good job with that because you can just see, you know, the powerful conversations that are being had and it's so important. It's so, so important. So well done there. From our own conversations with women in retail, there are some clear steps we can take to better support and empower women leaders. Based on your insights, what are some practical strategies that we can create here? Because you've done this great job of building a community, but how do we make sure that people are empowered to take this back to their businesses and that type of thing?

Jennifer:

Yeah, I think it's a really important question. So I think the first thing is keep developing and investing in your leaders, right? I don’t care if you’re a manager making your way up or your the CEO of a Fortune 500 company, you still need leadership development. So investing in that for your leaders, whatever that means for your company and women advocating that for whatever position they're going for hey, I need some leadership development I want to coach or I want to join this organisation or I want to attend this event. 

You know, that's going to help me, further my career and be more valuable to you. You know, it's so important for the retention and acquisition of your own employees to invest in them. So I think that is very key, you know for businesses to continue that you know at some point in your career you get to a place where there's no more training, right? And you're supposed to walk through this magical door of leadership and have all the answers and know how to solve all of the problems. And that's just not the case, right? 

Amie:

It’s not a destination

Jennifer:

No, I mean, it's a forever journey, right? So I think it's really, really critical for businesses to continue investing in their leaders, particularly on the women's side. And then I think the other key is businesses have to be flexible. You know, you have working parents and you have women that are, you know, again, wearing all the hats. And how can you be flexible to help them? I mean, you know, there are all of these fantastic women out there that are raising, you know, the next generation and they need some flexibility in their time and work schedule to do it all and to, you know, to have any kind of a balance.

Amie:

And I think that flexibility piece is becoming so much more important to people.

Jennifer:

Oh my gosh, yes. And those are the companies that are going to win, you know, leaning into that because you're going to have more loyalty, you're going to have buy-in from your employees. And by the way, they're going to do kick ass work because they want to be there. And they see that you're, you know, meeting them where they are within, you know, in the time in their life when they need it most. 

Amie:

Which is good. Yeah, no, that’s so true ok, so despite potentially not being at the pace we might like, there has been sort of progress in this area so I'm keen to understand how do you see leadership in retail changing in the next few years as the number of women in leadership positions continues to rise?

Jennifer:

Yes, I mean obviously we are, you know still a work in progress right there's always change to be made. I mean if you look there is study after study after study that shows that diverse boards and gender parity on boards within companies you know at the C-suite are just better bottom lines. I mean, it's factual, you know, companies with greater gender diversity have a 48% higher operating margin. I mean, 48% more than companies without. It is imperative that we keep working towards that. And by the way, it's going to help the companies and it's going to help their bottom lines. And if we continue on that path, and I think you're seeing that trend too, that boards are seeking out females on their board.

And they'll come to us and say, who do you have that might be a great fit. And we have oodles of talent that 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. And if we persist down that path, by 2030, we can reach gender parity in board and C-suite positions. And I think that's kind of the North Star to kind of keep at the forefront of your mind. It is possible.

Amie: 

Moving towards. I love that so if you had some advice for the next generation of retail leaders about making an impact what would your top recommendations be?

Jennifer:

I think, listen, your network is your net worth. I know everybody says that, but it is true. I've seen leaders, you get so head down in your bubble, you're doing the thing, right? You're working and you're in your own world, but you've got to pop your head up and continue to make those connections. Reach out to whether it's a mentor that you, someone you just admire and ask them for a coffee.

Typically women want to help other women, right? So, you know, the worst that's going to happen is they're going to say, don't have time in this moment, but here's another, you know, great person that you might be able to connect with that kind of thing. I think you just have to continue to build your network, put yourself out there, make it part of your job. You know, I've seen leaders get caught where they're really just, you know, honing in on the business and growing the business. 

And then, you know, they're on to their next opportunity, but then they take a look around and they're like, my gosh, I haven't spent this past, you know, couple of years building my network. I'm ready for my next, but what do I do? You know, where do I even start? And you're starting from the ground up, just constantly layer it in, layered into your job, you know, go to the events, have the coffee, reach out to someone that, you know, has a skillset that you don't have and you know talk to them about that how to develop that and hone those skills and I think listen just always be curious always be learning you know I think that again you know I'm such a professional development junkie there's it's a never-ending journey.

Amie:

We never stop learning.

Jennifer:

It's always a path, exactly and you know women are naturals at that right we're always on the self-development path you know, so that would be my best advice, yeah.

Women have to be their own change advocates, right? We are, no one is coming to, you know, help us but ourselves, right? And that is why you've got to become part of a community. You've got to build your own network. 

Amie:

You have to do it collectively together.

Jennifer:

Collectively, you have to advocate for yourself. And there are, you know, whether it's our organisation or others out there, you know, just put yourself out there, right? It's part of your growth path. It might not be on your to-do list this week, but you know, again, make it part of your professional development.

Amie:

Yeah, because it's so important to have those tools because I think often we get trapped in, know, someone might support me to do this in my career and I've seen that happen a lot where there's just an expectation that, you know, it's not us coming together to push the change. It's sort of, someone's gonna come  to me and, you know, it will happen in my organisation. But it doesn't need to be, you know, it should be led, sure, but it should start at the top potentially, but we're all part of it. And we all should be coming together to really help push forward.

Jennifer:

It's very true. It's about the collective, right? And you never know, you know, when that person is going to be meaningful. I mean, I see it all the time, right? At our events, you know, someone will meet and then, you know, five years down the path, they're working together because they met at an event. 

Amie:

I love that

Jennifer:

You know, and just had a connection, right? And women can feel it, right? Like you and I have such a nice rapport, like women immediately feel it and they're like, okay, you're my people. You get it. Right. 

Amie:

Yeah, it's so true.

Jennifer:

They're out there and they want to help other people. Yeah.