EPISODE 021 : 07/30/2021

Jennifer DiPasquale, Total Retail + Women in Retail Leadership Circle

Apple : Amazon : Spotify : Stitcher : TuneIn : Pandora

Jennifer DiPasquale is the President and Co-Founder of Women in Retail Leadership Circle, an association for executive females at leading retailers and brands, as well as the Co-Founder of Total Retail, a premier digital publication. In working with her retail clients, Jennifer helps leading brands find their unique proposition in the omnichannel retail market.

Host: Ned Hayes and Ashley Coates
Guest: Jennifer DiPasquale

Topics Discussed in this Episode

  • Detailed small business insights from Olympia, Washington
  • Small business resiliency and adaptation during COVID
  • Doubling community outreach during the pandemic
  • Opportunities for small business loyalty programs

Subscribe to our newsletter

Audio Transcript

Ned Hayes [00:00:01] Welcome to Spark Plug, where we talk to smart people working at the intersection of business and technology. Brought to you by SnowShoe making mobile location smarter.

Ashley Coates [00:00:15] Jennifer DiPasquale is the president and co-founder of Women in Retail Leadership Circle an Association for Executive Females at Leading Retailers and Brands, as well as the co-founder of Total Retail, a premier digital publication in working with her retail clients. Jennifer helps leading brands find their unique position in the market and on the solutions side, she helps her tech clients to deliver on measurable business goals for retailers and brands. Welcome Jennifer to Spark Plug 

Jennifer DiPasquale [00:00:44] Hi Ashley! Thanks so much for having me. 

Ashley Coates [00:00:46] We’re so glad to have you here. So, Jennifer, I’m wondering if you can start by telling us a little bit about yourself and what led you to your career in retail and retail solutions? 

Jennifer DiPasquale [00:00:56] Sure. So I am, as you mentioned, the president and co-founder of Total Retail Women in Retail and now newly formed Women Leading Travel and Hospitality. And so I’ve been in the retail space for 20 plus years now. When we originally when I originally started, I was part of Total Retail, which is a digital publication in the space. And since we have launched, we’re eight years old now and we’ve launched Women in Retail, which is actually in association in the space for all of the executives at leading retailers. And we recently launched Women Leading Travel and Hospitality catering to all of the travel hospitality verticals. So under all of those umbrellas, we have events that are really our sweet spot. Of course, we pivoted to digital with COVID, and now we’re hoping to come back to live events in the fall. We have research, we have a lot of podcasts, webinars kind of you name it, in terms of the channels reaching all of the retailers and travel and hospitality companies. 

Ashley Coates [00:02:01] Congratulations on your newest venture. 

Jennifer DiPasquale [00:02:04] Thank you, it’s been fun. 

Ashley Coates [00:02:06] Will want to talk a little bit more about the mission focused around helping women succeed at all levels? 

Jennifer DiPasquale [00:02:11] Sure. So when we were running total retail events, our events are invitation only director level and higher. So really pure networking functions where retailers can get in there and talk about their pain points and all of the issues that they’re dealing with and bounce ideas off of each other and those kinds of functions. We noticed that women were sort of organically and naturally congregating together. And so my co-founder and I kind of had the idea for women in retail and we did sort of a sample poll and said, you know, Hey, what do you guys think about this? You know what, if we launch this association, where are you getting your professional development and female networking? And they were like, Yeah, this does not exist for us. So we had found some white space. And then we basically put together a board of really killer females who just were leading the charge at the time in retail and said, What do you guys want? We will create whatever you want. We’re from the media side of things, but tell us what kind of content tell us what kind of event, what kind of support do you want? And so what they really wanted was a community of executives. They could hobnob with and bounce ideas off with and really kind of have like a year long relationship with the mission for us is really to champion these women, give them their community, bounce ideas off of, like I said, and really grow with and give them all kinds of content in the professional development leadership development space to help them become the best leaders that they can be. So when we launched, we launched our marquee event in the association at the same time because we didn’t want to just launch this great event and have all of this energy and have all these executives together for a couple of days. And then, you know, you go back to your day job and your real life and kind of the community and the fostering of the community sort of fizzles. So we we launched the association side of it in conjunction with the marquee event so they could connect all year long. And that’s really what we built as a community of women who support each other. 

Ned Hayes [00:04:33] Right. I know that your mission is to foster leadership development for all members. Yeah. And so I’m really curious, you said that it’s the director level or higher, but many of the most successful retail people I’ve met grew up from the show floor. They actually started as a frontline customer facing position. And so how do you foster leadership at that level so that you can grow a team to grow into those executive roles? 

Jennifer DiPasquale [00:05:00] Yeah, it’s such a good question Ned, so we when we launched, we launched with the intentionality of highlighting these women in these roles, director level and higher so that managers and folks under them could see them as champions in the space and that they could take our findings and leadership and development and really permeate that throughout their organization, right? And is there an iteration down the road for us of manager level and a mid-tier? For sure. Absolutely. But we wanted to start with these directors and kind of give them the tools that they could take back to their own team and train them and use our learning and development for their own teams as well. 

Ashley Coates [00:05:46] Jennifer, you mentioned that last year you pivoted to virtual events. How has your group changed since pivoting to virtual events last year and now that things are opening back up? Are you planning to do more in-person events? 

Jennifer DiPasquale [00:06:00] We took a huge hit, as everybody did in the pandemic. The bulk of our business is live events, so we had to pivot is kind of the magic word of 2020, right? Like, everybody had to pivot their business, as did we. So we took a deep dIve into virtual events. I think we launched every virtual type of event and tested every platform on the planet out of there. And we did find huge value and sweet spots within the virtual world. We ran a couple of events that were called women retail leadership days. And we basically since we’re catering to a high level audience, we knew they couldn’t sit in front of a screen for two and three days on end as much as they would love to connect with the community. So we peppered. We took a 30 long day event and peppered different things throughout the month. For them, keynote sessions, activations, coaching, kind of all of the all of the things. But over a 30 day period, we did that twice in COVID. Those were super successful. And then we also launched Pure Groups, which, to be honest, was super meaningful, particularly in COVID. We broke up our membership by title and levels so that CMO’s were connecting with CMO CEOs were connecting with CEOs so that they to allow them to talk through like, what is everybody doing in our sourcing wise and shipping and logistics sourcing issues and all kinds of things like that. So we spun those up so that these women could have like minded conversations and share discussions and figure out what the solutions are. So but yeah, it’s I mean, it was a challenge. Now we’re going back to live, so we are super, super excited for the fall we’re going to typically are women reach a leadership summit, which is our our big market that takes place every April. We’ve moved to October in Miami to be live this year and then we’ll move back to April in 2022. And then we have a slew of other events happening in the fall and then a ton planned for 2022. So fingers crossed. 

Ned Hayes [00:08:12] So is there a criteria that people have to meet other than having a title in order to to join the retail leadership circle? 

Jennifer DiPasquale [00:08:20] I will say our sweet spot is is really in the marketing and e-commerce space digital titles, but really it’s catering to any female in in that position, director level and higher. The content that we’re producing is much more title and even industry agnostic. We’re looking at the holistic development of the leader and bringing their best selves to work and what kind of tools and tips and tricks and all of that fun stuff can we feed these women to bring their whole selves to work? 

Ashley Coates [00:08:53] And speaking of all these amazing female retail leaders, I’m curious if you have any that you really admire or any leaders that have really made a difference in your career along the way. 

Jennifer DiPasquale [00:09:04] Oh my gosh Ashley, how long is the show? I could rattle off a dozen! There are so many leaders that I look up to personally that have mentored and spoken for our group. You know, Sara Blakely of Spanx? I don’t know if you’re familiar with her really amazing season. She’s just an amazing entrepreneur and she has four little kids, which is fantastic in its own right. But she’s amazing. I actually have the honor of interviewing Arianna Huffington this past March and Shelley Ibok of Sleep Number. We did an interview together. I mean, just fantastic leaders, great human, you know, giving back to not only females, but just in general to mankind and just really inspirational folks. I mean, honestly, we’ve had so many that that has been one of the silver linings of COVID. I will say, is that we were able to get hold of and top speakers that are typically on the road. Their schedules are crazy. So, you know, to bring in someone like Arianna and Shelley is phenomenal. And we will have folks like that on stage, live and in person in October, so as much as I love virtual, there is nothing like being in-person and having the energy of the room. 

Ned Hayes [00:10:26] What lessons, especially for retail success, have you derived from talking to these female leaders? 

Jennifer DiPasquale [00:10:32] Yeah, I mean, I think it’s it’s so individual and depends on your business, right? I think everyone is trying to meet consumers where they are in the moment right now. So obviously, personalization is huge. Experiential retail is huge. Figuring your your focus strategy buy online pickup in store is major. Dealing with your supply chain issues, like all of that, is being figured out in the moment. And truthfully, what we’ve seen in this industry is quite amazing. The digital acceleration that’s taken place typically may have taken years, and it shrunk down into a period of six to 12 months for these retailers. So what they’ve done is nothing short of amazing in terms of lessons learned, I think again, one of the silver linings is that these companies are really, really taking a good hard look at who they want to be in the world. And is there a nonprofit that they’re aligning with that is meaningful to them? Is there a sustainability angle that they can take or are they a profit for purpose driven brand like a Toms or a Bombas that is going to give back? Because I really think that consumers meaning consumers where they are right now means putting your brand out there and figuring out who you are and what you want to be in the world so that the consumers understand who they’re buying from millennials and Gen X Gen Z, like it’s all very purpose driven purchasing right now. So I think that has been one of the silver linings. Is these companies really coming forward and figuring out who their brand wants to be and what they want to support and what they believe in.

Ned Hayes [00:12:15] Any kind of cautionary tales? 

Jennifer DiPasquale [00:12:17] Cautionary tales, I don’t know if they’re cautionary tales, but I think every retailer is sort of trying to figure out their digital strategy going forward, looking at consumer insight. Are people going to be in store or are they going to continue with the e-commerce trend? So just sort of monitoring your data very carefully and sort of doing predictive analytics with all of your consumer data is going to be key to moving forward because it’s a tricky environment right now. I think all these retailers are super mindful of all of their data points and analysis in this moment and trying to bring out that crystal ball for what holidays look like and all of that good stuff. 

Ashley Coates [00:13:05] So going back to 2016 that year really marks the beginning of the #MeToo movement, and I would be so curious to hear your perspective on in the years since the #MeToo movement and other other progressive change, have you noticed any difference in the retail industry for women in leadership positions? Have you noticed any barriers that have come down or any other noticeable shifts that you’ve seen over the past few years? 

Jennifer DiPasquale [00:13:33] The it’s a difficult environment because women have been decimated in the workforce overall, particularly in retail, particularly women of color. So I know that we have forty one women leading Fortune 500 at the helm right now, which is the highest number that we’ve ever had, but it’s still only eight percent. So when you look at it from that umbrella, I mean, it kind of shines a light on on everything that’s going on. And that, I can say is is one of our missions is to put these women back to work. I mean, you talk to any retailer out there and they have open positions from floor managers all the way up to executive level. And you know, I think we’re still in a place where we’re fighting gender pay inequalities. You know, the pandemic really put the domestic responsibilities on the majority of the females. And so the workforce is now going to have to rebuild that. And I think retailers and all businesses really are going to have to look at how do we get women back into the workforce looking at their child care services and health plans and things like that and of course, looking at pay inequalities. And women really need to advocate for themselves to unapologetically negotiate in this moment. As far as we have come and we have come far, unfortunately, the pandemic really put us in a tough spot and we’re in a rebuild moment of time. I will say companies are looking at diverse employees, right? Boards are looking for for women to be. On the boards, they’re looking to put women in higher level positions so that there are champions within the company and that females can see themself reflective of where they want to be in the workforce. That is all part of the positive movement, right, is that people are looking for diverse candidates, right? 

Ned Hayes [00:15:34] Well, it’s been over 10 years since Sheryl Sandberg gave her her talk at TED Talk that led to the book Lean In. 

Jennifer DiPasquale [00:15:42] Yeah. 

Ned Hayes [00:15:42] And there have been some critiques of the book over time, but I’m curious if your perspective has shifted on that point or the points that Sheryl made. 

Jennifer DiPasquale [00:15:49] Look, you know, Sheryl is a brilliant female and I’m in no position to criticize her book. I think what she did at the time was again highlight gender and pay inequalities and try and start a movement of women really advocating for themselves. So in that respect, it’s fantastic. I mean, do we have a long way to go? Absolutely. Can women have it all? Absolutely. Can they have it all at the same time? Maybe not. And I think that that is part of what pandemic has highlighted is that domestic responsibilities, of course, falling to the women is hugely challenging in and of itself, let alone. If you’re going to pick a person in the household to take over the domestic duties, it’s going to be the person that makes less. So of course, you know, in a lot of cases, that is going to be the female. We have a ways to go, to be quite honest. 

Ned Hayes [00:16:47] So one of the interesting things about reading the story of technology history is that technology is often taken domestic tasks off of women in the household. If you think of washers and dryers, dishwashers, all of these and not that this should not be shared tasks, but all too often that has landed on female members of the household. Right? And so do you see technology also changing in retail and taking some of the mundane tasks off of the plates of people, men or women so that they can be a more effective customer facing advocates? 

Jennifer DiPasquale [00:17:23] Yes. I mean, my gosh, the technology that is coming to market is incredible in this moment, and you’re going to, you know, you’re going to see it evolve, of course, over the next five to 10 years. But I do think that there is still something to connectivity in store and customer connection in store. Right. Especially especially now more than ever, the technology is going to lend itself to streamline and help these retailers with all of the A.I. innovations and everything in that world. However, it still is going to be a connection point for the consumer. You have to kind of figure out as a retailer, what do we want that connection to look like in-store mobile, online social media wise? Like, what is our connectivity of all of these channels? How do we make sure that everything is in alignment and we’re serving the best needs of the customer, regardless of the technology that we have in place? 

Ned Hayes [00:18:19] So some of the technology changes that have happened influence what kind of information we can get about people and how readily people will share their information. So when you’re kind of creepily in the background understanding some of these preferences and location, that kind of data is being challenged. Retailers who are paying attention are starting to ask people for their actual preferences. Do you like ice cream? Do you want us to know your location? You want us to send you things. So when people are more proactively volunteering information, they tend to respond more happily because they know what’s happening. You see this trend continuing? 

Jennifer DiPasquale [00:18:54] I do. I mean, you know, there’s always going to be privacy issues and data breaches and things like that. But fraud prevention has come such a long way that I do think that there are, you know, especially with the loyalty piece of it, right? If you’re loyal to a brand, then it’s only going to build over time with offers like that and allowing kind of that door to open up for consumer insight and a little more familiarity with the brands. 

Ashley Coates [00:19:24] Can you actually talk further about loyalty, Jennifer? How important is loyalty right now? Does it still matter? What role does it play for retailers in today’s world? 

Jennifer DiPasquale [00:19:35] Loyalty is obviously wildly important, especially in this moment. If you can really craft and hone your loyalty programs, it creates a lifetime customer lifetime value that is huge for these retailers. I think what’s really interesting in this moment is that people are really looking at where they’re buying from. And what I mean by that is what do these brands, as we talked about before? What do these brands stand for? 

Ned Hayes [00:20:08] Right? Well, at SnowShoe we’ve seen some interesting things happen with loyalty before COVID people were more willing to to trade actual physical cards back and forth. And now post-COVID, people are saying, Oh wait, you have a hands free device that can actually allow loyalty. Great, we’ll go hands free. Do you see different things staying after COVID? Do you think retailers have changed practices that will remain post-COVID? 

Jennifer DiPasquale [00:20:34] I do. I mean, I think a lot of the touchless and contactless technology that is in place, you know, you see it really everywhere now. Restaurants and hotels kind of cross-industry in this moment, and I don’t think that that’s going away anytime soon. I think there’s probably going to be different iterations of that down the road and new and exciting things. I think probably with the technology that is coming up, you’re going to be able to walk up to someone and scan their sweater and say, Hey, I love that sweater. Do you mind if I scan your tag, pop a click and you’ll have it in your mailbox the next day? So I think all of that is to come. It’s where the industry was headed. It was just the digital acceleration of everything. 

Ashley Coates [00:21:14] Well, thank you so much, Jennifer. We do have one more question for you. Yeah. Which is what is your personal mission and what do you want to be remembered for? 

Jennifer DiPasquale [00:21:23] My personal mission, while I have three children, I have two boys and a daughter, 15, 13 and nine. And if you ask them literally any day of the week, I will say if you say, like, what is your what does your mom want for you? I want them to be happy and healthy, and I want them to be good people. So that is really if I am raising good humans, then I feel like I’ve done a good job. Part two of that is, of course, the work that we’re doing. I mean, I really want to help as many females as we can in this space, give back to them and get them back into the workforce, champion them up through their organizations, help them find their dream job, whatever that may look like, right? Maybe a part time job, it may be the CEO of the next Fortune 500 company, whatever that looks like to them and give them a community who will support them along the way. 

Ned Hayes [00:22:22] Great to talk to you today. Thank you so much for your time, Jennifer. 

Jennifer DiPasquale [00:22:25] Yeah, of course. 

Ned Hayes [00:22:49] Thanks for listening today to the Spark Plug podcast hosted by me, Ned Hayes, and brought to you by SnowShoe Snow.sh for smarter mobile location, Spark Plug is a wholly owned property of SnowShoe all content. Copyright 2021 Spark Plug Media.