Finding the Fire: Shannon Flanagan on Retail, Resilience and Career Purpose

A resume can look flawless while the real story stays hidden. We sit down with Shannon Flanagan, a retail and retail tech leader and the founder of Retail Women in Tech, to talk about what actually shapes a career: the messy pivots, the painful exits, the values you violate when you start performing for other people’s scorecards, and the small decisions that quietly change everything.

Shannon shares the moment in her mid-20s when organizational change work helped her find a clear purpose: creating the conditions for people to love what they do every day. From there, we unpack three pivotal turns, including a “what did I just do?” detour that later became essential, plus the reality of going through four layoffs and learning to pause instead of sprinting into the next job. We also dig into comparison syndrome, how boundaries can disappear when you become a founder, and why “fit and fire” is a practical test for whether a role is still right.

We go deeper on what makes great leaders and great hires in today’s market, especially as AI recruiting filters and endless interview loops reshape the job search. We talk mentorship vs sponsorship, transferable skills, career mobility across retail merchandising, planning, and technology, and why learning isn’t measured by a grade or a title. We close with a powerful perspective reset from a service trip to Honduras and what it teaches about gratitude, joy, and impact.

If you care about career growth, leadership, women in tech, and the future of retail technology, listen now, then subscribe, share with a friend, and leave a review with the biggest choice you’re making in your career right now.

Shannon's Bio

Shannon Flanagan is a retail leader, connector, author, speaker, and founder and CEO of Retail Women in Tech. Her career began in retail stores at 18 and has since spanned merchandising, consulting, sales leadership, general management, technology, and executive roles across some of the industry’s most recognized organizations.

She has led strategic initiatives as a senior executive at Gap Inc., Lands’ End, and Macy’s, and has partnered with hyper-growth startups and Fortune 500 companies through her work with Accenture, Slalom, Talkdesk, Writer, and retailconnected. Across each chapter, Shannon has stayed close to the human side of retail - the people, teams, customers, and communities that make the industry dynamic.

Today, through Retail Women in Tech, Shannon is focused on creating stronger pathways for women across the intersection of retail and technology. Her work centers on connection, career mobility, parity, and helping people build careers with greater intention and purpose.

She is also a RETHINK Retail Top Expert, NRF Top 50 Retail Voice, RetailWire BrainTrust member, advisor, and soon-to-be-published author of Choose, Don’t Chase, Your Career. At the heart of her work is a clear belief: when people are supported in doing work they love, the impact reaches far beyond the workplace.

Transcript

The Why Behind The Resume

Ben 0:46

Some careers look linear only after we edit out the messy parts. Shannon Flanagan has built the kind of career that reads impressively on paper. A career originally heading in another direction after college, she found her way into retail where she moved through merchandising and buying, worked in consulting, led strategic initiatives and transformation work inside major retailers, built go-to-market motions and technology companies, and now leads retail women in tech, a global nonprofit movement dedicated to driving parity and strengthening career mobility across retail and technology. She has held leadership roles with Gap Inc., Land's End, Macy's Accenture, Slalom, Talk Desk, Writer, and Retail Connected. She is a Rethink Retail Top Expert, a Top 50 NRF retail voice, a retail wire brain trust member, an advisor, speaker, and soon-to-be published author of Choose, Don't Chase, Your Career. That is the resume. But the more important part of Shannon's story is the why behind it. At twenty-five, while working through major organizational and technology change, Shannon found the through line that would shape the rest of her career, to create the conditions for people to love what they do every day. Not in a soft, abstract way, in a practical, deeply human way. Because when people are fulfilled at work, that energy does not stay inside a company. It ripples into families, communities, and the broader world. That idea sits at the center of this conversation. What follows is not a polished career highlight reel. It is a real conversation about fit, fire, failure, layoffs, comparison, purpose, boundaries, technology, opportunity, and why the most important career decisions are often not about chasing the next title, but choosing the work that allows us to become more fully who we are.

Rich H. 2:50

Welcome back to another episode of Retail Relates. Judy, I appreciate you joining us on a short notice today.

Judy S. 2:58

Of course, I'm always glad to join.

Rich H. 3:00

I appreciate it. See, that's why you were a star student in my first class. And I'm excited to be able to introduce you to Shannon Flanagan. She is a person that I've gotten to know. Of course, you get to know somebody when you're in the back of the van driving through the hills of Honduras doing good things. And you are finally here.

Shannon F. 3:20

Finally. It's about time.

Rich H. 3:22

Yes. Uh well, you have a few things going on, so you can be forgiven.

Shannon F. 3:27

Well, I'm thrilled to be here. Can't wait to chat with you, Judy, and get to know you more. Um, and so yeah, let's let's get it going, Rich. Where hard question are you gonna start with?

Rich H. 3:36

Well, we've read your bio. It is impressive. We would expect no less. So, what we're gonna do is we're gonna have you curate that down. That's my word of the month. And see if you can isolate three pivotal moments, and they can be personal, professional, but three pivotal moments in in your lifetime that have brought you to where you are at this point in your life.

Speaker 3 3:57

Well, I'm old, so there are more than three, but I do have a couple. So one happened at the age of 20 font. I started in stores at 18. I um went through May Company's executive training program. I was a merchant, I was a buyer. And while I was at Sephora, I realized that I loved all of the special projects I was working on. And I had a lot of people around me who were in consulting at the time. Prior to that, the Anderson Consultants of the World, et cetera, didn't hire for experienced talent, but they'd opened up the aperture. So I went to work for Accenture. I'm trying to find purpose in being in corporate America. At the same time, we're implementing, you know, transformational integrated planning systems like tops down planning, bottoms-up. Nobody was adopting it. So a couple of things happened at that moment. I got really interested in organizational design and change management and leadership. And I was also trying to find purpose in corporate America. And it's there I discovered my why, which is to create the conditions for people to love what they do every day. It's been my through line, certainly getting to materialize it in spades, I hope, today. Um, but I believed in the ripple effect that if people were thriving in the jobs that they had, they'd carry that energy home to their family and their friends and the community around them. So that's the first pivotal moment is that it inspired me to become a change practitioner. So the rest of my career, I think, has followed suit with that drive and passion and frankly skills. Now, fast forward to another pivotal moment, which is more a WTF moment, which is I had been in retail. So I'd gone into consulting, I went back into retail. I was with Gap Bank, then I was with Land Zend and Macy's, and then back to Gap Bank. And frankly, I got tired of solving the retail problems like vendor managed inventory, which just didn't seem to die as an initiative. So I decided to try my hand at sales because I wanted um business development, I wanted technology experience, failed miserably. Um, and ended that year with the what did I just do to my career? Now, if you're smart, so lessons to you students that you can have these times in your career that you're like, that was a waste, or I didn't learn anything. I could not have done the jobs I did later without that experience. Uh and then the big pivotal moment was to um accelerate my retirement plan to run a nonprofit and and share stories of of people in the world that we live in. So decided to go all in last year and uh build the nonprofit that is retail women in tech and write a um book about the stories of women in our industry and those of us who are choosing, not chasing our career and doing the work that we love.

Judy S. 6:48

Is retail something you always wanted to do?

Speaker 3 6:51

Oh no, no, no. So I was gonna be a lawyer. Uh thank God that was not the path I took. So I got into stores working at a department store at age 18. I do have a moment that I was merchandising a gooseneck. Do you know what a gooseneck is? Does anybody know G Rich? Do you remember that language? I don't even know. Like piece of a tea stand or a forestand. Yeah, for tea stand or a four-way, and it's the thing that sticks up on top of it and you put an outfit on top. And I remembered that moment, I was like, oh my God, I love merchandising product. And I was in the juniors department. I had the opportunity to go into corporate while I was in college in a part-time executive role where I was working with the luggage department and getting to go out into stores. And I was a history major. So again, law was my path, but I was offered the opportunity to go into their executive training program. And thank goodness I did. I can't imagine loving another industry um better or actually thriving.

The Hidden Value Of History

Rich H. 7:48

You mentioned history. Did you get a major in history? I did. Like for reason.

Four Layoffs And What They Taught

Speaker 3 7:54

Well, and I will tell you, Rich, I did not know the value of that. It was not until, I don't know, maybe maybe 10, 12 years ago, how much I realized it played into the work that I did. So as somebody who's led strategic transformations, right, that's kind of my like core space that I've done is that it's about building uh a narrative. And I hate using that word, it's kind of overused, but telling the story as to why the change matters and to inspire people to do that. Well, what do historians do? They go and they take all of these different data points, right, and create a point of view and kind of a recommendation of um where the world is and where it needs to go. So I think the degree has been very beneficial to me and and my career and wouldn't change a fruit tea in China. So my advice to students study what you love. Don't study to get a job. Study to do what you what you're passionate about. Cause then your grades go up, dude. Well, that is true. For a semester, failure. But did history and graduated Magna Fumel. What's the challenge or setback that taught you something lasting? You guys are giving me all questions that were not on the sheet. My layoffs. So I recognized um about a year ago that I was like, oh my goodness, after having an incredibly successful career for almost 20 years, that I had four layoffs in a row. Two of which made total sense. One was the sales role, one was due to COVID, right? There was no business and retail. But two were heart-wrenching, in particular the first. But I would not be doing what I'm doing today. The book would not have happened without that experience. The personal life that I chose to lead as a result of that would not have happened without that challenge of rejection.

Rich H. 9:39

All right. So I want to lean in on that a little bit because in five minutes, what we discovered is the degree you got wasn't necessarily structured around the career you have, but that's okay. You are openly talking about four layoffs, which our generation was trained not to talk about those things. We are not supposed to show our emotions on our sleeves. We're not supposed to show fallibility and anything that may be perceived as weakness, but you're talking about it in a very positive way. What was that moment and how is that fueling you now? And you you answered it, but I guess I want to dive into a little bit deeper because I've I've had a similar journey. So I'm very curious to hear yours.

The Power Of Sitting In Between

Speaker 3 10:29

This is something that with our interns we talk a lot about because it is perceived in our society as failure. I would argue it's our greatest times of growth. And because what ends up, you're forced to change. And you have to think hard around why were the reasons that were maybe valid, but you also, I think it made me dug deep to believe in the things that I could bring to the table and why it was about fit, not skills and capabilities necessarily, right? So you will have times, and there's somebody who told me many years ago about leadership is that you know, you can't, it's oh God, let's see if I can come up with it. I'm not gonna remember his formula, but as great as you are, it doesn't matter if it's not the right fit. It could be the wrong leader, it could be the wrong time. And so I think those moments had made me pause. Like two of them, like, yeah, no-brainer, didn't hurt my feelings at all. And the ones that did, I had to dig deep as to why that was the case. And it often came down because I had a personal relationship with somebody that I felt like there was a violation of trust. Uh, digging deep into both and separating what were my capabilities that I still know and I believe to be true, and then what was maybe the personal aspect. And then I will close, and it's something that's a big part of the book is we don't honor these transitional moments in our life where we have a disruption, an unexpected one, and we want to rush through to solving for that moment versus pausing and going, What did I learn? Let me sit with this and let me grow in this space in between the moments.

Rich H. 12:03

I'm gonna go a little bit further, but I warned you this is going to happen. So if you want to take 20 minutes and get an espresso, and I can call uh Randy and tell him that you're the one holding up the conversation.

Shannon F. 12:16

Oh no, I mean, Rich, you and I can go. So, no, you go for it.

Rich H. 12:20

What I'm interested in is there's obviously we want to learn more about your career and the things that you've learned, but you are hitting powerful lessons right from the beginning and you're wearing those openly. Was it gradual over time that you learn to accept those things that happened and draw energy from it? Or was there an epiphany at some point where there was just that shock to the system where you said, you know what? I've got to do this differently.

Speaker 3 12:49

Both. So the epiphany was the first layoff. I mean, I was completely blindsided. Uh, and what I took from that moment, now I had the luxury to do this because I had an incredible severance package. But I decided, as somebody who was the breadwinner, mother of three kids, you know, very successful climbing the corporate ladder, who was driven by to-dos, I made a very purposeful decision when that layoff happened to not create to-do lists and to live in the moment and really explore what this idea, and and I'm not a spiritual guru, but this idea of the of Zen, right? And digging deeper and really reflecting on what it was in my life and how I wanted to show up and what I needed. So that was an epiphany. Um, and that was a huge turning point that put me on the trajectory that that finds me where I am today. Where the slower burn is, is that it's taken me now a well, I guess about eight years since then to actually have the, I don't want to say confidence. I was gonna say a dirty word, but the conviction to go after doing what I believe I was I'm supposed to do. And that's been a slower commitment, like the slower realization I'd always felt like a uh square peg and a round hole, and I don't anymore. And God, does that feel amazing?

Rich H. 14:14

I can imagine. So you're gonna tell me you were an original member of the imposter syndrome club.

Speaker 3 14:18

Oh no, oh no. So I will tell you, I wasn't even on to this thing. I've never felt like an imposter. Never. I was really confident. I knew what I was great at. Now, was I great at, was I great at reading the room and adjusting who I was for the audience and recognizing that maybe just always showing up as my true self was going to drive the the impact and outcomes I wanted. No, that's what I had to learn. So, no, it was not imposter syndrome. Somebody shared with me comparison syndrome. And that's what has plagued me. That it was because every role, not every role, 95% of my roles since the beginning of my career have been brand new. And so I did not take a traditional path in the kind of roles I played in organizations. So I was measuring my success in terms of I'm not maybe climbing fast enough. I certainly want, I mean, I was a VP at 34, so I don't know what measurement I was playing that with. But fast forward, I live in the Bay Area. I have friends that have retired at 45 who might not have had the glorious in careers in terms of impact and outcomes that those two words drive the kind of work that I that I do. Um, I also have been dealing with it uh pretty intensely, in particular this last summer, that now as a founder, I'm comparing myself to other founders and how many hours they work and what they're giving up to do that. I've compared myself financially, I've compared myself as it relates to titles, and I've compared myself now to hours equate to quality and impact. And they not don't necessarily. So that's more the thing I deal with pretty regularly still.

Rich H. 16:06

I I will admit it's the first time I I've heard that and and stripping away the the label because labels often get us into trouble. And instead just looking at the the comparison. I mean, if you look at consumerism and how it ramped up playing off history post-World War II, it was feeding off a comparison and saying, well, you don't have what the people next door have, what the Joneses have, and so you've got to keep up and take on all this debt. And I see this generation of consumers, and I think by influence, you and I buying less or buying smarter because we're realizing that comparing possessions or comparing degrees or comparing things like that isn't what's necessarily giving us happiness.

Speaker 3 16:49

And I think that comes to that point personally in this endeavor is recommitting. And we have to recommit to everything we do every day, our relationships, our choices, et cetera. But it was recommitting to values. So to the students out there in the world, I decided right out of college to prioritize balance in my life. But I grew up in a world where women were working their tissues off and the primary at home. And it's not to say we don't have that to some degree today, but it's definitely the balance is a little bit more equalized than it was. So I prioritize balance. And you know what that meant? I worked from 8 to 5, 5:30. I didn't open my laptop at night, I didn't open it on the weekends. And it's one of the big pieces of advice I give to up-and-coming rising uh stars like you, Judy, but also new parents. Because when you create boundaries, right, people do respect them. So I was able to have an incredibly successful career working 45, 50 hours a week. Now I'm a founder. And guess what? I started to do compare myself to the people who are working 15 hours a day, seven days a week. I now work from seven to six and on the weekends, I'm working the most I've ever worked. I now don't have boundaries. It's something that's caused some issues in my personal life because my family and my friends are like, you're not here, you're not present. And now I'm having to deal with figuring out the boundaries in this world. And what I realized is that by buying into the narrative that as a founder, I need to be working 15 hours a day, seven days a week, I was violating my values because my values are the diversity and the balance across all the things that drive us as a human being, which includes our family, our friends, our times for Gray's Anatomy. This is something I process and work through daily. But once I realized it was a violation of my values, it's become a lot easier to quiet that voice.

Rich H. 18:53

And it it stifles innovation, I find. For the time that I stepped out of being a corporate executive and and leaned into having my own agency and taking on projects, I found myself not able to turn it off and just step away because I felt like I always had to be gunning, especially when I'm the one driving the income. If I'm not making the call. So even if I was done by lunch and I had turned in what I needed to turn in, I still felt compelled to do something. I have a friend of mine, by contrast, Judy, we interviewed him, and he owns an agency, owns a couple of companies. And when he hit a wall, he went traveling with his son to minor league baseball uh games across uh Central and South America. What it turned out was that he developed a passion for it. He was doing market research, and now he has ownership in several minor league teams, but it was through that break and that discovery that it led to innovation that sometimes we don't have.

Speaker 3 19:51

Well, and Rich, something that I still struggle with. So as much as I say this, right? So I've been able to work through the comparison part. What I'm still struggling with to this day is it is what I wake up and go to bed thinking about every single moment of my life. Now, I'm pretty good at shutting off. So last year I had the good fortune of traveling to 14 different cities, a couple of different countries. I turned 50, there was lots of celebrations. I spent time with my daughter and Rich with retail ROI in Honduras. But it is super hard, though, to create the space. And I'm telling you, I'm failing at it, is to go take a walk. But I absolutely 100% agree that we need the space for creativity. We need the space to be in nature to fuel our souls to be able to do this incredible work. So now that's my 2026 struggle and objective is to be able to give myself the grace for the space.

Rich H. 20:51

So you have been involved with several retailers, you've been involved with consultants, you've done sales, you've worked with nonprofits in the past, you founded a nonprofit, you're writing a book. When you get involved with something, when you decide whether it's work or personal or passion or purpose, what are you looking for in that? What are you looking to achieve or get out of it before you say, you know what, I'm in?

Speaker 3 21:18

So it comes down to the why that I had at 25. I want to create the conditions for people to love what they do every day. You actually reminded me of this, which Judy, this is something to call out that I had forgotten. It's also around potential realization and actualization. Now, I I really focused in on that concept and that language earlier on. And I think then I decided it was, I didn't think I know. I decided that that's a bar that's super high. We never arrive, right? We're always on a journey. But when I look at both, if I was to tie together the personal and the professional, was how do you create the conditions for people to feel their potential, right? Lean into it. And maybe it's potential is actually, I'm gonna have to rework this. You guys have inspired me. Potential is the wrong word, right? But again, to be who you are and celebrate that and find the work that's the best fit while having fire to do that. It has been that through line throughout the course of my career. And then the decisions might make. And one of the questions you guys had posed, and it's a little bit different, but what I'm looking for when I engage with experiences or opportunities, especially ventures. And I didn't know the answer to this question. I found it really insightful when I did it. And I actually brought it up with my my president today that it's white space. And that term sounds very business focused, but there's something about I think every Space I've been in, partly because I've had all brand new roles, right? So I'm crafting something that doesn't exist. But where is there an opportunity to drive impact that's not already in motion? And I do think innovation is a completely overused word, but to innovate right in ways that people haven't done before.

Rich H. 23:05

I wrote this down impact not already or always in motion. And I think I don't know whether you've used that phrase before or whether in the conversation just came out, but I would trademark the heck out of it because I think that to the extent that I've been able to get to know you, that sounds like a defining statement.

Speaker 3 23:26

It is. And it's relative to like what we're doing here at Retail Women in Tech. There are a lot of activities and communities and initiatives that have great intentions to bring women to sitting at more seats at the table in all aspects of what we do. But is it really doing that? Is it just your networking and then what happens when you leave the room? So as we built this nonprofit, the impact is what is going to change the world. So, no, but I I I thank you for that, Rich, for calling that out. I actually have a trademark I'll share when I share some closing advice to the students out there. But Judy, your turn. Rich and I could obviously talk forever. So let's pause. We'll both shut up and give you the stage for a second.

Judy S. 24:15

I was just gonna ask to get to where we are today. Is there something that you did day to day that you think was the key to your success?

Fit And Fire As A Career Test

Speaker 3 24:22

So I'm not gonna answer that directly, but I'm gonna um answer it in a way that has inspired me that is at the core, what gets me up every day. I don't know if you ever watched Charlie Rose, but he was on PBS and he curated the most incredible interviews with people from every different aspect of um humanity, right? And really talked about their stories, their journeys, et cetera. And in my mid-20s, what I observed with those that were older in their career is that they had perseverance. They had passion. They never retired. I never wanted to retire and quit working. So I was always really inspired by these people who had passion and perseverance for what they wanted to do. So that word, one passion, like just naturally comes from who I am. So that one was an easy win. The hard one, but the one that pays off is the perseverance. So that is what gets me going through every day. And I used this phrase earlier, and I'm particularly true with the decisions I've made in the last year to go all in on the nonprofit, to write the book and write and have many more that I want to write. And I'm digging deep into my retirement, is that I have to recommit daily to being true to myself. And that ain't easy. It's sure rewarding, but it ain't easy.

Judy S. 25:49

So, following up on that, would you say that there is a trait that you see in other people that you would believe would be effective leaders in their future?

Speaker 3 25:59

So, this is gonna come back to maybe my trademark that I think I want to have that that um was uh inspired as I went through telling the stories of others and myself is this idea of fit and fire. So I recommend if I was to give the advice to all of you, always have a fire in your belly for whatever you're doing. And when the fire dies out, then you need to pause and question is it the right place? Now, that fire could go almost to nothing and then get some gas. Like it's not the second that the fire starts to die, that you go running, right? There's shit work that can turn into and terrible situations that can turn into awesome. So that fire does not need to be roaring all the time. And in fact, that's a misnomer if you think that's the case. But if the light has gone out, you don't see a fuel supply coming anytime soon. Pause. That should be the constant. The fit, though, changes over time. So there are times that something makes sense based on where you are. And the fit could be, I need to do this hard work that I don't love and I'm not totally interested in, but it is gonna help me get where I need to go. Or the fit is this is what I need to do because I have a new um child, right? Or my parent is sick. So I think the flexibility around fit and that evolves. But you have to also respect and appreciate that you might not fit in in that time and place given your life with the work that you have. And if you don't have, if the fit's not right and you don't have fire, then I think I give you carp launch to get the F out of there and figure out what is gonna work.

Rich H. 27:35

Yeah, because if you if you stay in a situation like that, and and I really respect the fact that you said the fire may be close to being extinguished. It's not, you don't go in every day and it's not gonna be a barrel laughs and it's gonna be no, it's gonna be challenging days. But you get to that point. I I compare it to I get up in the morning, I look in the mirror, and if today's the day that my values and goals don't align with where I am, that's a day that I have to decide that it's time to move on, not to walk in and disparage the organization or try to move it where it's immovable, but that's the moment where I have to say, and it and it may be a job I love, or it may be working for someone I love, or but it doesn't align anymore. That's the day you have to say, it's time to be uncomfortable.

Speaker 3 28:22

Well, and I think, Rich, for me, you know, I get that we're older, right? So we have learned these lessons. And but what my hope is, is that we can accelerate that for the younger generation. Be purpose-driven in what you're doing and really question the idea of the value of money and title and status in terms of fulfillment, taking care of yourself and what drives you and the values that you have in exchange for maybe some of the things that we've traditionally thought were important, like lots of money. That money can disappear in a heartbeat, right? Now, you have to balance it. Money did give me the opportunity to do this, but I've never struck it rich at all. This is a big gamble on myself. But I think those gambles, if we can encourage rich, these younger generations, to stay true to the feelings they have in their heart, I would have done what I'm doing now a lot earlier.

Money Titles And Life Trade-Offs

Judy S. 29:18

That's definitely great advice. Um, but I feel like once once you're starting your career, it's kind of hard to choose something that you feel like would feel a lot of fulfillment from, especially knowing that you have a lot of expenses you need to cover. So I feel like it's kind of like a two-way in a way.

Speaker 3 29:34

So I was gonna say though, I think as somebody who's, you know, dipping into retirement and having to get really smart about what you realize is how little you need. And what's the payoff? That comes down to the question of fit. There might be a time that the right fit is when you want to focus in on the making the money and the titles, et cetera, and you're willing to give up values and peace and fulfillment. And that's up to everybody to decide. But Rich, to your point earlier, in a consumerism-based environment, like how many pairs of shoes do we actually need? How big does the house need to be? Yes, we have bills, but the facts of the matter out there are, and I don't know who I'd quote, that as long as your everyday expenses are covered, there is not a huge increase in happiness beyond that. And I think that's part of the opportunities to break down that success.

Rich H. 30:24

And I think it's a great conversation, but you're you're almost redefining the difference between a career and a job. And it's okay to have a job that pays the bills that allows you to do things that fuel you, like go to Honduras to work with Daisy and do something really meaningful. And we will get to that a little bit later. But you kind of alluded to the fact that your first semester in college may not have been the best. And I was gonna say, hey, want to compare GPAs because Judy would probably laugh at who wins the lowest GPA.

Shannon F. 30:54

Oh, oh, oh, let's do it. Let's do it. What do you think, Judy?

Rich H. 30:57

Who goes first?

Shannon F. 30:58

So no, Judy, I want to I'm because I want to know what that she thinks is a bad GPA.

Judy S. 31:05

Mine was mine was pretty low. I was at 3.1. My false amount.

Speaker 2 31:09

Oh so the point.

Rich H. 31:13

So I was going to do that.

Shannon F. 31:15

But we could have not scripted that better. All right. So what do you think Rich and I have? I mean, because I'm talking way lower than that. 2.5?

Judy S. 31:27

Pardon me? Like a 2.6, 2.0?

Rich H. 31:30

My first semester, 1.33.

Shannon F. 31:34

Oh, he beat me. Of course he did. I had a 1.9.

Rich H. 31:37

Yeah. My first semester, 133. And but the point I was gonna make is, and there was a point in time where I would have never admitted that, but nobody's asking what your GPA is back in. Yeah. Flip side, nobody cares that I got a 3.9 when I went to William Mary and got my MBA.

Speaker 3 31:53

Yeah.

Rich H. 31:54

Exactly. Yeah, well, I graduated as a, you know, 3.9. What you do with your time and how you impact or what leads to it. And I think I didn't have that realization until I was well into my 40s that the things that I thought were of value really meant nothing, and they mean nothing to me now.

Speaker 3 32:14

And that's to the point, Rich, and what I was saying to you, Judy, is like, I and I appreciate that, you know, Rich and I are now in our 50s. And the best thing about getting older is wisdom. Right. There's a lot of things I don't love, but you do get wisdom. And I know that wisdom can't be forced upon people who have not had the experience. But the wisdom that I hope that your generation can start to internalize is don't let work destroy your life. And Rich and I have seen, and we've also experienced the impact that a crappy job has. And again, you have to do crappy work sometimes. I mean, with the interns, um, it's actually happened for somebody who is outside of this, who was at ETL last year, that had this misconception that being a CMO was going to be like walking apart. And I was like, no, like in our organization as a startup, we're still rolling up our sleeves and build, you know, doing data dumps into Google Sheets and sorting and sifting. Is that what you're working so hard for? Is to not have a life when you're an EVP? Because you're supposed to be always on and you're traveling everywhere. And I think that there's this romantization around like these titles and the access you get, et cetera. But all of it comes at a cost. And I I say to my kids, I have three teenagers, life is a series of trade-offs. And you can, and those trade-offs shift over time. And they're okay to maybe sometimes be incongruent. But I do think for your generation, it's like, why learn from us?

Judy S. 33:47

Well, going back to how you guys shared your GPAs, I think that's amazing. And I really hope you guys keep that part in the podcast because speaking of comparison and how you were mentioning it earlier, just today I was looking through LinkedIn and I saw somebody graduated with being on these lists every semester and found myself comparing to that. And being like, I was never able to do that. And I feel like um studying was never mm my strength, I think. Like I always I feel like I always put in more effort than other people, and then they'd end up getting a better grade than I would, even though I'd be stuck in the library for hours. So it's really great hearing that. And I feel like so many other students would appreciate hearing that perspective. I just thought I had to say that.

Speaker 3 34:25

So Judy, and I think Rich is gonna echo me. I don't think I'm gonna go far off on this one. Or in our third cohort of interns. I know within five minutes if I'm gonna bring them on or not. And I don't look at, you know, yes, do I see their GPA on a resume? What I look for energy, commitment, drive, curiosity, want to learn something new. And those are qualities that do not show up on a resume. And even when I would do hiring before the interns, I would tell people, I want to know who you are. And there's a lot of talk about this idea of a career narrative. And again, these like these words that we get stuck in. But it the jeunesse qua is what's going to connect you and make you special. But at the end of the day, I'm hiring based on drive and passion and commitment and the belief that anybody can learn something if they care enough. So, Rich, I'm curious in what you feel about that topic.

Rich H. 35:26

So I agree with you. And I I think that what I would say is does a GPA matter? It may or may not. Does a title matter? It may or may not. But it's what drove you to it. Like I can interview somebody who had a 3.8 GPA. I think I saw the same LinkedIn post. And if I gain an understanding as to what drove them and what they were doing with it, and it's part of their brand, and I hate to default to that, but I'm going to, then okay, I get it. Conversely, I might interview somebody who has a 2.5 GPA and they struggle to get that, but the struggle made them hungry and it made them passionate, and they have other interests, and they're just a more well-rounded person. And I know that that person is someone, if they hit a brick wall, they're going to keep going. And one of the things that I tell my daughter all the time is learning isn't measured by a grade. And success isn't measured by a salary. Now, money's important, grades are important, and you've got to, but it's it's much more than that. And I think that's one of the things that I don't think, Shannon, we teach enough is, and I don't like to, I don't want to necessarily default to how do you brand yourself? It's who are you?

Speaker 3 36:44

And it's going to say in your why, right? And what gets you out of bed every day? That's what we want to hear. That's what we're hiring for. And it's what you deserve.

Sponsorship Mentorship And AI Hiring

Rich H. 36:54

But I'm going to pivot a little bit. What is your greatest satisfaction in being a leader?

Speaker 3 37:01

Oh, seeing people thrive. It's those moments, and again, it's the creating the conditions for people to love what they do every day. But when they I don't know, when they feel good about where they are.

Rich H. 37:14

And I knew that was going to be your answer. Not because you said it before, but instinctively I knew. And because of that, and it's why relationships and networking are so important, is that I'm going to compare it to the New York Yankees. You can go out and buy all the expensive players you want. You can pay top contracts. It doesn't guarantee you a championship. Not at all. And as a coach, as a manager, as a leader, if you really love what you do, you take great pride in finding the undiscovered, finding the underdog, finding that team player who's going to gut it out day in and day out, who wasn't given a chance by other clubs, and they end up becoming your 12th person or your leader or your MVP. And so that's why degrees matter and grades matter, and but it's the total package.

Speaker 3 38:03

Well, it's the five-tool player, right? Of course, you need the person who's going to be your power hitter. But I'm going to answer it differently than I thought I would. So what I would say is that in we, we, you know, at Retail Onatech, we're so thrilled with our mentorship program. We're blowing it up this year. But this idea of sponsorship, right? And so as you're going through and you're cultivating these relationships, but for those speaking to the audience who are hearing this that are not 19, 20, 21, 22, whatever it is, how are you sponsoring someone? Because I think that's where Rich, the role of a sponsor, is cultivating the pieces of somebody that they don't maybe know that's there, but we can see. So we're not just telling them and mentoring them. We're actually sitting in the rooms on behalf of them. And we're driving and encouraging them to follow those pieces of them. And it's not easy, you guys. It's not easy to follow that. And when I decided to step outside of the box, and I hate to use that was a really overused phrase for a long time, not in my thinking, but in my actions, is when I finally found the way that I can have the greatest impact in the world.

Rich H. 39:11

The challenge today within careers, and I've I've made this joke before, that it's almost like I'll have my AI contact your AI because HR departments are using AI to filter resumes, and professionals or students are taking AI to take their resume and search for all the keywords. And you get the social media reels that are basically saying, here's how you take your resume, look at the 120 keywords and optimize it. And it's like a gentic hiring as opposed to what you're doing. Yes, it's women in retail tech, but it's about a connection and it's about meeting people and learning about people and empowering people and driving people forward and the industry forward.

Speaker 3 39:56

Well, and that inspires several points, but uh we'll see how many I get to. So, right, we believe one-to-one connections are a superpower. When you create a connection with somebody, you're not just doing it for yourself, right? It's a reciprocal, I care about you, I hear you, I want to get to know you. And so that's part of what we tried to foster. We also are fostering the skills, the upskill skilling, the transferable skills. So I talked about a perfect storm grooming. One of them is the AI recruiting models because it's going to model the cultures and the population that already exist. We've also gone, and you guys, the amount of stories I hear now, people going through, and Rich, have you been hearing this six, seven, eight interviews? I don't know how these companies have the time for it, to be quite frank. No, and we've said, Judy, to our college student interns, like, they're like, nobody's getting back to me. I always like, well, welcome to the party, because you could be as SVP and nobody's getting back to you. What's going on with that being the case? I can we can only speak for retail, or at least I can. We are hiring for unicorns and we're hiring for deep functional expertise. But our Power of We Wednesday interview series that we have done with over 60 women and a handful of allies, none of them had a linear career path. They all had spider webs. And so one of the things that we are really focused in on is how do we change the conversation and open the aperture for tech companies, retailers, media to value the diversity of life experiences and career experiences that make us the best of who we are. So we're trying to create one-to-one connections, but also the skills, the transferable skills, the upskills, the ability to tell that story to somebody, because you can't get a job without a connection and you can't get a job without the skills. You need the magic of those things coming together.

Rich H. 41:54

It's a wonderful place to be able to come into and to be able to forge those connections, whether it's the skills or whether it's the people, and be able to create opportunities that way.

Speaker 3 42:04

And that I mean, that's at the core of what we want to do, right? Is to build this workforce engine of that's driving to mobility. Yes, parity, right? That's the ambitious goal. But mobility, because we also know, Rich, within a retailer, if you want to go from merchandising into planning or planning into merchandising, that's almost impossible. Let alone I'm in merchandising and I have a passion for technology. Where do I go? I'm in technology. I have a passion for retail. I can't get in there. And we're gonna grow as an industry if you just put your business net on. It makes sense to do that.

Rich H. 42:41

It's the reason I don't like rom coms because if the two just had a communication in the first five minutes, I could have skipped the rest of the movie and gone to dinner. And you have an industry that's saying we can't find talent. You have talented people saying we can't find jobs. And it's like, okay, let's skip the popcorn and introduce you.

Speaker 2 43:00

I'm gonna borrow that. That is exactly, and that's ridiculous.

Speaker 3 43:04

In our industry right now, Judy, I don't want to scare you guys all from coming to retail. And Rich, these are the numbers I read last week in Retail Dive. Nothing to do with what happened this week. We have layoffs at 125% year over year from last year. We're the highest, I think, impacted industry with layoffs.

Rich H. 43:24

And that'll be a whole other conversation because it's one of the areas where I am maybe encouraged isn't the right word, but optimistic that with tech, with agentic AI, when used properly, that it'll open up opportunities for a wider range of talent. But we have to get through that right now.

Honduras And A Reset On Gratitude

Speaker 3 43:42

Well, and Rich, that is what we that's so a part of who we are and committed to is that we need to foster the spaces for women to fill those roles. Because I absolutely agree. AI is not necessarily going to take your job, but somebody who knows it is. And we need to redefine in our industry. So we're planning to hopefully put together a think tank that define what's the AI operating model of the future. AI is not just a technology, it's a way of life. And we need to completely rethink the way things are happening and who are at the table and where to make those things happening. So, Rich, yeah, let's pick up on another conversation. I could go another four hours on that topic.

Rich H. 44:23

We will put together a round table. So I do have to ask one question before we go to the rapid fire. Because we did have the opportunity to experience retail ROI together and to go to Honduras to the Kapan region and the importance exactly and the importance of giving back. And I think I still have a hard time expressing what that trip did. I I know you've done a better job putting it into words. What Did it mean to you and why is that important from a life learning perspective?

Speaker 3 44:52

I mean, this really came down to being a mother of three. I come back to something that's been said way before I ever existed. Children are not born with hate. Hate is learned. Trauma changes people. So I have a philosophy that I think is shared by many parents because there's the whole conversation around nature versus nurture. We come out who we are. We're like stone, we're statues, we're stone. Our genetics, our nature is really damn strong. But what nurture does is it could it could chisel out of bouquet or cut your leg off. And so when I think about what we were doing, Rich, is it's starting at the youngest levels, right? And how do we build a world and build the flywheel and the momentum that there's less hate, there's less violence, there's less trauma. Because to me, the one the most heartbreaking thing is a child in trauma. And so that's what really moved me around what we were doing. And then to see, and this comes back to what we were saying earlier about what do we really need. And I think you see the humanity and the value of somebody being thoughtful and just touching and connecting. They don't need a McMijan, they just want a meal. And so I think it comes back and it connects you to the fact that what world are we living in in America in our definition of success when we have these people that are lining up for a plate of rice. And we have these in these college kids so concerned about their 4.2. So it brings back to me the gratitude that we we have to live with. It doesn't take away from our own personal pain. But Rich, I don't know if that answered the question or not, or how you felt.

Rich H. 46:40

There's no right answer to that, but I think you you framed it very well. I and and you and I were both were there for that moment. The the moment when we were with the families that basically live next, they they live in well, I'm not saying next to it, they live in the landfill. And so basically you take a poor community and the trash the poor community gets rid of is up in this landfill, and they're living off of that. And and this tells you a lot about your your perceptions and how they can be wrong. Your daughter and Nikki's daughter had cameras and bubbles, and I'm thinking, why? This is ridiculous. And yet, when they were taking pictures of the kids and they were blowing bubbles, and the smiles and the laughs and the grins and and the father who held the his daughter and was fixing his hair for the for the picture, I'm sitting there saying, How simple is it to make somebody smile and laugh? And if I were in charge, I would have said, Don't bring that, bring more rice. And yet that probably meant more in the stickers and things like that. The stickers that's gonna come back to the stickers. Yeah, it it does put it in perspective. And I bring that back and I say, you know, within working with our associates and working with our families and working with our customers or our patrons is how do you bring those moments of joy, realizing that you know, there are tough lives out there, and it's it's our job to try and make it a little bit better.

unknown 48:01

Yeah.

Rich H. 48:02

All right, we're gonna have to lift this up, Judy. Now, you know that she's anticipating one of the questions, and let's see if you or I can hit it to start.

Speaker 3 48:08

Oh, let's see. The hardest one.

Judy S. 48:10

Let's see if you get it. I want to say it's the dinner with three people.

Speaker 3 48:15

I had to think hard about that one, and I'm not saying I've got the right answer, but I tried not to overthink it, and I didn't really think about them all together.

Judy S. 48:23

Is it the city? Go to city for a day.

Speaker 3 48:26

That's the one I struggled with.

Judy S. 48:28

I was gonna say that one, but then I was like, okay, maybe it's the dinner one. Okay, then I would love for you to answer that question.

Speaker 3 48:34

Well, I'll answer both, but that one was really hard. All right. Really hard. Because there's so many places I want to go, but if I only get to be there for 24 hours, that was the hardest part. So my initial like part was Mount Everest. And I was like, I don't know. I mean, you arrive, like, that's not a 24-hour day. I'd love to see Tibet. I mean, I've been in the mountains of Thailand, like how different would it be? So then I decided a place that, no offense, that I would love to go for 24 hours and only 24 hours is the pyramids. Because I don't think I would ever take the trip out there otherwise. And I want to see, I mean, I'm just absolutely in awe. And you made me come back to a place. Now, when I was at NRF, Rich, I don't know if you were up on the fourth or fifth floor where there was the Amex booth and you could get this cool to me luggage pad tag if you stood in line and they had a big board of all the places you were gonna go. And the one place I wanted to go was the Mel D, but I'm not going there just for 24 hours. That needs to be two weeks of decompressing.

Rich H. 49:31

All right. So I'll ask the question that uh that I know Ghee would have asked, and it isn't on the list because I haven't added it yet. But if you had the choice of traveling into the future or traveling into the past, you can't impact anything, but you can choose how far in the future, how far in the past. Where would you go?

Speaker 3 49:50

It would not be past. I mean, and maybe that's partly not to toot my own horn as a historian that I uh internalize and listen and read and feel all the things that have already happened. And things are better today than they've ever were. As much as we like to think that we're retracting, we do in some ways. I'd like to believe that life is like the cha-cha, right? Two steps, you know, all over the place. I wouldn't go too far in the future, though. Uh I think I would maybe go 50 years. I'd want to see what my grandchildren's life was going to be like. And I would hope that I would feel so your children's, Judy, that I would hope that I don't have to fear for them. But that's a deep question, Rich.

Rich H. 50:33

He's made that his signature. I I don't know whether I should have asked it if it's his signature, but it's okay. He's not on. It's okay. All right, Judy, you asked the final question.

Judy S. 50:42

So, what is something you've purchased on a trip that you regret buying? Oh, so I'm sorry.

Speaker 3 50:46

This was the question I had no answer for.

Rich H. 50:48

All right, so go in the opposite direction. What's something you bought on a trip that was on a whim that you just absolutely love?

Speaker 3 50:54

I'm very frugal. So I don't spend on things. I spend on the experiences. So I'm gonna answer it differently. It's not a thing, it was an experience. So I was in New York with my daughter this last September, and we bonded and spent countless hours of my life watching Gossip Girl together. We'd shopped all day on Friday and Saturday morning. We were gonna go hit all the Gossip Girl stuffs, and I splurged. Again, I'm living off retirement right now and I'm frugal, but I spent to have one of the bicyclist guys, Chuck Tux or whatever, take us on a Gossip Girl tour. And that was worth everything. So it wasn't a thing and it was an experience. But I'm at the Emperor's State Hotel. I look at the drinks and I was like, oh, I really want that drink. And it comes in and it's got Gossip Girl like stamped on it.

Rich H. 51:48

I really respect that answer because it's one of those a material possession. Oftentimes you're not going to remember it, and you can lose it. I mean, hey, you know, you never know what life's gonna what life's gonna happen, but nobody can take away the experience of being in New York with your daughter going through Gossip Girl and doing the the Central Park and he plays the music.

Speaker 3 52:09

And I was like, Pi, we're not like the cheesy other people. Like, we're doing Gossip Girl and getting the thumbs up everywhere. So yes. Did Judy did I answer your question? Do I get a pass fail on that one?

Judy S. 52:20

Yeah, I love that. I love gossip girls, so you definitely get the pass.

Rich H. 52:24

All right. Well, Judy, do you want to close the show? I mean, I will say thank you to Shannon. This is this has been a long time coming. We've talked about it for quite a bit. We will definitely have to do a round table and and delve into a couple of topics, but this was well worth the wait. I greatly appreciate you investing the time today.

Speaker 3 52:40

What a great way to end my friday, while my Friday is not totally over like yours. But uh at the core of what we do and what I do every day is again uh creating the conditions for people to love. And that doesn't matter. You know, we honor every season. So, Judy, it's you and your peers, it's high schoolers, it's those who are just starting out, it's those who are in the messy middle, no matter what age, it's those at later stages. We have to learn on our own. But if we can close the gap a little bit of the pain that we've gone through to do the work that we're supposed to do, um, I hope we inspire you guys to have at least a voice in your head that's saying, Is this really what I want? Those are choices you have to make.

Judy S. 53:21

That is definitely a question that I think about as well. Um, but it's great to hear your advice on that. And thank you so much for joining us today, Shannon. It was great speaking with you and learning from your experience.

Speaker 3 53:30

My pleasure.