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The CEO Series with Jennifer Drake

Strategy Focused Group · 2026-06-24 · 52 min

0:00--:--

Key moments - from our scoring

Substance score

37 / 100

Five dimensions, 20 points each

Insight Density7 / 20
Originality6 / 20
Guest Caliber11 / 20
Specificity & Evidence9 / 20
Conversational Craft4 / 20

Jennifer Drake, founding principal of Avenel Field Group and 25-year retail veteran, shares her unconventional path from pre-med student to C-suite leader across Nordstrom, Saks Fifth Avenue, and Banana Republic. She traces how a chance encounter with Pete Nordstrom during college sparked a retail career spanning flagship stores, off-price operations, and field leadership of 400-store fleets. Drake credits mentors like Paige Thomas (former CEO of Saks Off Fifth) with recognizing her potential before she saw it in herself, and describes how a personal crisis - her mother's cancer battle during a critical transformation project - fundamentally reshaped her understanding of culture, trust, and human-centered leadership. She now advises mid-size to enterprise retailers through Avenel Field Group, focusing on how corporate strategy actually manifests on the sales floor and in customer interactions. This conversation will resonate with retail executives, store operations leaders, and anyone building consulting practices who want to understand how ground-level credibility and authentic field experience drive advisory impact.

Key takeaways

  • →Starting on the sales floor and maintaining hands-on store involvement is critical for leaders to understand how strategy translates to customer experience in practice.
  • →Employee experience directly drives customer experience and organizational health, requiring leaders to build genuine trust and culture rather than just performance metrics.
  • →Mentorship and sponsorship from senior leaders who see potential in people before they see it in themselves can catalyze career growth and confidence at scale.
  • →The retail industry demands agility and willingness to pivot from traditional career paths, requiring leaders to balance passion with discipline when facing uncertain terrain.
  • →Investing in people closest to the customer unlocks performance, strong culture, and brand consistency more effectively than desk-based strategic planning.

In this episode

  1. 1Early Career Path: From Pre-Med to Retail
  2. 2The Nordstrom Foundation and Leadership Philosophy
  3. 3Career Progression: Sales Floor to Store Manager
  4. 4The Defining Moment with Paige Thomas at Saks Off 5th
  5. 5Personal Crisis and Lessons in Empathetic Leadership
  6. 6Transitioning to Entrepreneurship and Avenel Field Group
  7. 7Paternal Influence: Resilience and Pursuing Passion Over Practicality

Mentioned

NordstromSaks Fifth AvenueBanana RepublicSaks Off 5thAvenel Field GroupSouthwest AirlinesLinkedInJennifer DrakePete NordstromPaige ThomasBlake NordstromHerb Kelleher

Guests

Jennifer Drake

Topics in this episode

Southwest AirlinesHerb KelleherNordstromSaks Fifth AvenueBanana RepublicAvenel Field GroupSaks Off FifthPaige ThomasBlake NordstromPete Nordstrom

Questions this episode answers

What experience does Jennifer Drake bring to retail consulting?

Drake has 25 years of retail leadership experience, having worked as a salesperson, department manager, district manager, store manager, and head of stores across Nordstrom, Saks Fifth Avenue (managing 100+ stores during the off-price business split), and Banana Republic, culminating in field leadership of 400-store fleets of off-price and designer flagship stores on the East Coast.

What pivotal career moment shifted Jennifer Drake's approach to leadership?

A LinkedIn message from Paige Thomas, then CEO of Saks Off Fifth, invited Drake to lead 100+ stores - a scale jump that taught her sponsorship, mentorship, and the power of having confidence in people before they have it in themselves. This opportunity transformed her understanding of leading at scale and transforming business through influence.

How did a family crisis shape Jennifer Drake's leadership philosophy?

When her mother was battling breast cancer, Drake had to step away from a critical transformation project on Black Friday and leave the business for six weeks. She watched her team step up, which shifted her perspective to prioritize trust, culture, and humanity as foundations for sustained performance, not just high performance metrics.

What is Avenel Field Group and what does Jennifer Drake advise on?

Avenel Field Group is Drake's consulting practice that advises retail organizations (starting from mid-size) on how to keep strategy simple and authentic by focusing on field realities - how customer experience is actually won or lost on the sales floor through salesperson interactions and the customer experience in stores.

What family inspiration drove Jennifer Drake to start her own company?

Drake's father, a veterinarian who left law school mid-way through his second year to pursue his true calling, taught her that the right path is sometimes the hard path, pairing passion with discipline. This lesson of resilience, courage, and willingness to bet on yourself even when the path is uncertain inspired her to build Avenel Field Group.

What our scoring noted

Our reviewer’s read on each dimension, with quotes from the episode.

Insight Density

7 / 20

The episode contains a handful of memorable principles (the kite analogy, communicating the 'why' of hard decisions, trust as the engine of sustainable performance), but the 52 minutes are heavily diluted by the host narrating his own anecdotes, audience shout-outs, and mutual affirmation. The ratio of usable insight per minute is low for an operator audience.

are you flying the kite or is the kite flying you?
labor is not just a workforce management tool like you described. It's people, it's somebody's job, it's their family, it's their routine, it's their sense of security

Originality

6 / 20

The strategic content recycles well-worn retail and leadership frameworks - inverted pyramid, 'stay close to the customer,' 'if everything matters nothing matters,' culture-performance link - without adding new angles. The kite analogy is the only genuinely memorable and distinctively framed idea.

clarity drives execution. Um, teams really need to understand priorities. Um, if everything matters, nothing matters
experience can give you a pattern recognition. Like, you can identify it. But curiosity, I think, keeps you from getting stuck

Guest Caliber

11 / 20

Drake is a genuine field-operations practitioner who ran 100+ store fleets at Saks Off 5th and held senior roles at Nordstrom and Gap Inc., giving her real at-scale credibility. However, she is currently a solo consultant in early-stage formation rather than an active operating executive, and the episode's title ('CEO Series') overstates her role.

Paige had the confidence in me before I had the confidence in myself at scale
asking myself, can I really go from running one flagship store to a hundred stores?

Specificity & Evidence

9 / 20

The episode earns credit for named executives (Paige Thomas, Richard Dixon, Blake Nordstrom), specific stores (White Plains, Tyson's), and a rough timeline (customer letter circa 2003), but there are virtually no hard metrics, revenue figures, or quantified outcomes - the specificity is anecdotal rather than evidential.

my first employee leadership job was three employees. Then it was seven, 10, um, and I was, you know, up to 85 employees
this is back probably in 2003, um, they wrote to Blake Nordstrom

Conversational Craft

4 / 20

The host repeatedly inserts lengthy personal anecdotes (Dubai, Mongolia, Pakistan, his wife's retail stories) that consume guest airtime, asks only broad biographical prompts, and never challenges or probes an unsubstantiated claim. Questions are formulaic career-interview fare with no meaningful follow-up.

I wake up in the morning and I log in and they said, uh, the project we're working on that was supposed to start in two weeks, we're going to put that on hold
So what do I do now? How did you guide that?

Conversation analysis

Computed from the transcript - who did the talking, and the words that came up most.

Share of words spoken

  • Jennifer Drakeguest65%
  • Host35%

Most-used words

back31customer30retail26career22store20nordstrom18leadership15journey14experience14life14today13field13worked13story13manager12school12

Episode notes

Last week Friday, our guest was Jennifer Drake, the Founder and Principal of Avenel Field Group and a 25-year retail leader who’s run stores and field organizations at Banana Republic, Saks OFF 5TH, and Nordstrom - a 400-store fleet, off-price business, and the designer flagship on the East Coast. She now advises retailers on how to operate better and elevate the customer experience.In this episode, Jennifer reflects on a career built from the sales floor up, the turns she didn’t see coming, the decisions that tested her, and what she’s learned about leading people through change.If you missed it, be sure to watch the episode!For previous episodes of The CEO Series, please visit / strategyfocusedgroup . #sfgtheceoseries #livestream #podcast #entrepreneur #motivation #dubai

Full transcript

52 min

Transcribed and scored by The B2B Podcast Index.

Jennifer Drake: I actually started off college as pre med, but I learned really quickly being in the labs wasn't for me. I took a retail class my junior year. I then attended a lecture series where we had Pete Nordstrom visiting M. I just fell in love with the company with the idea of such a fast paced career. That was it. I was hooked. What I like most about working in retail is people. I'm out in store a lot. You know, I'm never in office, which is the best part of my job. And have an opportunity to really get to do things with customers. Whether it's talk about fashion, go in the fitting room, see what a customer's trying on. My career at Nordstrom actually began as a salesperson six days after graduating college. Then I went through our future Nordstrom leaders program and became a department manager. And I've held various regional merchandiser roles as well as store manager roles. And everything that I've learned in those different jobs has prepared me for the job I have today. You get this feeling knowing you can make a difference in people's lives. Customers that I've been friends with for 15 years, employees that, that I've hired as interns and now they're store managers. Retail is a team sport. It takes a whole bunch of people to run the store. A piece of advice that I would give is really be a student of the business, seek out a mentor. This is her five year flat. It's really good to have somebody as a sounding board. Really listen, you're gonna learn so much from the people that do it every single day. This person started with us back in 1990 and she's celebrating 20 plus years of service with us. People might think this is a job at the mall. It's just so more than that. We create 30, 40 year careers for people. I started as a salesperson and didn't know I was going to be a store manager and certainly did a lot of different jobs along the way. And I'm so lucky that I did. I absolutely love it.

Host: Good morning, good evening. Depending upon what part of the world you're in, if it's Friday, it is the CEO series where we explore career journey journeys, the trajectory, the detours, right, left, turns u turns along the way to shape extraordinary leaders. Our guest today is Jennifer Drake, founding principal of uh, Avenel Field Group. She's a she, she has 25 years retail as a retail leader who's run stores and field organizations. At banana Republic Saks Fifth Avenue where we met Nordstrom's, a 400 store fleet of off price business and designer flagships on the East Coast. She now advises retail retailers on how to operate better and elevate the customer experience. How are you? I am.

Jennifer Drake: It's really, really great to see you. Um, you know, I was telling, um, you that I can't believe how long it's been and how quick time passes, you know, since we first met back in 2022.

Host: Yes, yes. It flies by, it flies by. Fantastic journey. Um, I met you when you were at off sacks as sacks of fitness. The correct way to use that. Um, walk us through that journey. You know, your video kind of showed a lot of that, but walk us through kind of the ins and outs, high points, low points, kind of give us a snap.

Jennifer Drake: Yeah, yeah, I appreciate that. In kind of thinking about this conversation, it's been a little bit of a fun look back in history, I would say, to look at my career and think about kind of all the pivots and the twists and the turns. And one thing that's really common that I thought about a lot of, um, is it's definitely not linear. Um, you know, it's not one of those things that you expect. Um, my first dream was actually to be on Broadway. That didn't really work out. So I think, you know, you know, intersecting with and learning about retail as a career was the best thing that could have ever happened to me. And as I said years ago in that video, um, I had this great opportunity to sit at a roundtable with Pete Nordstrom, you know, in a small group, which was, you know, as a, as a 20 something, um, a great introduction. And, you know, what I learned in that conversation was all about the Nordstrom way and the inverted pyramid and the idea that the customer is the front line and the top of the company. Um, from there, I really kind of was drawn into retail for a lot of reasons. I mean, I like shopping, let's start there. Uh, fashion, but business, people, psychology, leadership, the pace, um, performance pressure. I felt that I could be kind of creative and strategic at the same time. And I was excited to start my journey on the sales floor. I think the common thread as I think back on my retail journey is all the roles and the people in the field. Um, and I became really passionate about how the strategy that the company puts forward presents every day in real life. And I think that's probably what's led me to where I am today, which I know we'll get into, which is the word entrepreneurship, which I can't ever believe is in kind of my dictionary. These Days. But I think after years of transformation and being in large companies, I saw this opportunity where I would keep coming up against people asking for my advice about the customer, about the field, about integrity of the brand. And this is kind of where this idea of Avenel Field Group came from. Simply that the customer experience, experience is truly won or lost in the field. Um, and when you invest in people closest to the customer, you unlock really great performance, real strong culture and consistency for the brand. So it's been an exciting journey, for sure.

Host: Yeah. You know, I, I was intrigued when you talked about. When you talked about, uh, uh, m. Mr. Nordstrom. Um, I had a. A chance to hang out with Herb Keller, who started, uh, Southwest Airlines in New York, uh, one evening over adult beverages and amazing, uh, stories that tell. And I think you picked the same thing up from, from, from Mr. M. Nordstrom is the fact that sometimes he'd say he'd come there and he'd go outside and he'd have him load, Load baggage on the plane, stand at customer service to see how, what he could do to help. He'd talk to customers that were waiting to board a flight. So when you look at that employee experience, and one of the things that video showed to me from my side was the ability to connect with the people that work in the stores. The. This is what I always tell CEOs at C Suites and boards is that the employee experience translates to the customer experience translates to the health of the organization.

Jennifer Drake: It really does. I'll tell you one of the, you know, the stories that sits with me is after, you know, meeting, um, Mr. Nordstrom and telling my parents that I was going to choose a journey in retail after going to the new house school and studying communications and advertising, I'm going to move to Manhattan, I tell them, and I'm going to take the job offer right at Nordstrom. And they're like, what's the title? What's the salary? And I'm like, I don't know, it's commission and, you know, starting on the floor and having to, like, put the stock away and count the inventory, you know, and answer the phone. And it really teaches you, um, about dealing with the customer. So I'm really glad that I had the great fortune of starting kind of on the sales floor.

Host: Yeah, that's building. Building from the ground up.

Jennifer Drake: Yes.

Host: So looking back on your journey, was there a defining moment? M. Where to shape your leadership path? You know, your video, you said I was going to do pre med, but now I'm in retail and I'm going from here.

Jennifer Drake: Yeah.

Host: Another ladder.

Jennifer Drake: I was reading so many moments, but one, that, one that stands out. You know, I remember when LinkedIn kind of started and you know, I was like, I'm going to get into this and I think it's a great way to have access to people you wouldn't normally have a conversation with. So, you know, I had been kind ofactive on LinkedIn. I was working at Nordstrom, I was a store manager. I was kind of had my head down doing my job. And I get a LinkedIn message from, um, Paige Thomas. She was at the time the CEO of Saks off fifth. And you know, I'm thinking about my. Oh my gosh, Paige Thomas, she was the Nordstrom Rack chief merchant. And honestly I thought, what does Paige Thomas want with me? You know, I'm like, okay. So, you know, I'm like, I send them note back right away like, uh, I'm available anytime you're available. Um, we get on a call and, you know, we spoke about the fact that Saks Off 5th was going to split apart the businesses and, you know, they needed somebody, a stores expert and someone with deep stores experience. And Paige and I had intersected, um, early in my career as a district manager for the market that I, you know, was in. And she had visited the market and we identified, identified a growth opportunity in the D.C. market. And she took it back and worked with the merchants and it really grew into an incredible, like, growth story. And I didn't realize she actually remembered that years later. And you know, she remembered the work, she remembered the reputation that I was building and how I showed up. And that conversation then took me from running one store, um, to asking myself, can I really go from running one flagship store to a hundred stores? It felt like a leap that I couldn't take. And Paige had the confidence in me before I had the confidence in myself at scale. And I think that opportunity taught me how to lead or begin to think about leading at scale and having influence to transform business. Um, but more importantly, it taught me sponsorship and mentorship and the importance of seeing potential in the people before. Sometimes people can see it in themselves. So that was a very defining moment for me.

Host: Yeah, she saw something there. It. I always advise people, advise students or people that whoever they are in their career, you never know the impact that you're going to have on people.

Jennifer Drake: It's so true.

Host: So always be on your best behavior because you never know where something's going to come from. I got, I did a project last, uh, week With a big client. And, um, they said that they heard you speak in Pakistan three years ago. I didn't even remember I'm Pakistan quite a bit, but I remember which one. And we want you to work on this project. So the same story behind that is that you never know.

Jennifer Drake: No, you really don't. And you know, you know, when you said that, it. It kind of spills over into a memory that I. Stands out to me that I just want to mention. You know, um, the late Blake Nordstrom, you know, he used to visit stores a lot. And I'll never forget one of my first store manager gigs. He visits. And I'm so nervous, right. So we're walking the sales floor and I pause and I let him walk ahead. And I'm watching him literally take every opportunity to interact. And he would never, like, not have a m moment where he would walk over and have, uh, a moment to engage with a salesperson, a stock person. And in that moment, you know, I recognized that you don't realize or recognize your influence potentially until much, much later. And people remember those moments. They might be 10 seconds, you know, and that interaction sticks with people. So I couldn't agree more with you, Ron.

Host: Yeah, it's important that people that are rising on the so called career ladder, if you want to call it that now understand that, because those are. They don't teach you that in undergrad. They don't teach you that in business school or, uh, DVA programs. They don't teach you those kinds of things. The interaction, the small things that you do for people. And I love the fact that. And Herb told the same stories about how he would go out and stand at the counter. He would go out and talk to the people who were putting luggage on a plane in all that heat. But he would spend time with it and it made a difference. So as we talked through your journey, was there periods that were particularly difficult period?

Jennifer Drake: Oh, yes.

Host: That probably could take another couple hours because we all have gone through those. Uh, so what do I do now? How did you guide that?

Jennifer Drake: You know, when I think back, I mean, there's definitely been the typical challenges, but one of the most, I would say, difficult periods in my own career was when my mom was battling breast cancer and I had just gotten into this very big leadership job I was trying to transform. We were remodeling a store. You know, I was in it. I had moved away from home. I was down in Florida. Um, and I had always been a very hands on person in my career and very involved and Present. But during that time, you know, I had to step away on and off. And I'll never forget, it was Black Friday morning. I'm ready to go out on the floor and cheer the team on. And I get the phone call, um, that it's, you know, towards kind of the end of my mom's life. And I'm thinking in my head, oh, my God, it's Black Friday. I, um, know that sounds kind of crazy, but when you're in it and you're really young in your career, you're trying to prove something. Um, and I had to step away. I had to step away. You know, I got on a flight, I left Black Friday morning. I had to lean on my team. Um, and I would say in that particularly challenging moment, I had to trust. Um, this idea of being a good leader meant, um, you know, not being involved in every single thing. And honestly, it really changed me. Um, you know, I watched people really step up in a meaningful way. Yeah. Um, my team carried the business. I was out of the business for, like, six weeks.

Host: Yeah.

Jennifer Drake: The way people showed up and supported me, it made me recognize that the word culture isn't just something you say. Um, it's really a lot about what people feel, you know, when they're going through something hard. And I think that experience really shifted perspective for me to not only develop people, but trust people and create a culture where the support you're giving them is real. And not only that, it made me more of a human leader. Um, I think everybody has something going on outside of work. Um, everyone's going to face something. And when a business environment creates an opportunity to make people feel supported, they become more committed, not less committed. And that lesson has really stuck with me, that while high performance matters, of course, culture, trust and humanity, I think, are really what sustain performance over a period of time. So that taught me a tremendous amount in leadership.

Host: That's an amazing, amazing story. Um, and I think that needs to be talked about more, especially for younger people that are graduating from universities and looking for the next step. Reality has to set in.

Jennifer Drake: Yes.

Host: Because it's a totally different environment than probably we can't. I finished school a lot longer than you did, but over a period of time, all that's changed. This journey that we sold people on.

Jennifer Drake: Yeah.

Host: Is not there anymore because everything is being disrupted. So it is.

Jennifer Drake: It's an environment that you have to really be more agile in. I mean, I thought this exact journey in a box was going to look a certain way. And then in that moment, I Think I recognize pivots and all of those things that you're describing.

Host: Yeah, the pivots, you know, they described as pivots. But a person is sitting there dealing with that. And I said, well, they may call it something else that a little bit. It could be a little, uh, word that could be used as a result of that. So as you gave us insight on that and that was brilliant the way, by the way that you framed that and talking through that, you know, um, having to deal with, you know, your mother and all of those kind of things and walking that through. So, so the learnings from that, you were able to the small bits and you were able to build that into your brand and caring for people, talking to people on the sales floor, even though you started on the sales floor, you know, and doing that, um, do you see that's important for leaders today too?

Jennifer Drake: No, I think there's nothing more important. I mean, I always, you know, get energy from going to stores. I mean, in my more recent jobs over the last couple of years where I've been the head of stores, you know, whatever the title might be, really, I think the time that I spent in the store trying to solve the problems was much more productive than sitting at a desk, staring at a screen, a meeting. Yeah. So I think that, you know, especially given all the change that we're seeing in retail.

Host: Yeah, yeah. So you're, you tell us about your new company.

Jennifer Drake: Oh, my goodness. Avenel Field Group. Okay. Well, it's a little bit of, uh, you know, consulting, but I, I don't even really love that word. Um, I think part of it is just really offering advice and learnings. I also just wanted to challenge myself to see if I could build something like that. I mean, I'd always worked for big, large companies and you know, it's interesting with the changes in technology, um, and I think I wanted to challenge myself and ask myself. I had watched my father build, um, a software company outside of his business and I thought an LLC my dad had that I could do this. And what's been interesting is trying to take the ideas that are sitting with you or the experiences you've had and making something that's, you know, about you but for others. And you know, I really wanted to, um, be able to help organizations, people, you know, starting out mid size, you know. And so I created this idea where I'm just going to start my own thing and I built my own website. I mean, I'm, I'm doing it all. I think part of it's the journey and wanting to learn what's possible and what I can do. And it's something I had never thought about doing. But I kept kind of bumping up and confronting this idea that people wanted some input or advice, and maybe I had enough experience at this point in my career to offer something. So it's an eventual.

Host: Hold on. You said maybe, maybe. M. Maybe. Nah, maybe it doesn't work in that phrase. No, you had it. So as a result of that, you're now advising companies as to how you can move through, uh, navigate through all the changes you've talked about. You're talking about the technology, you've talked, and you're, you know, brand, uh, off brand. You know, I say off brand with those level of stores. In doing that, you've been there, done that. So why would you would be the perfect person to talk to. You gone through the complete transformation?

Jennifer Drake: Yeah, I mean, I think having drawn on experiences and lessons and, you know, even thinking back and, you know, hearing mentors in my head, I want to be able to help companies keep it simple.

Host: Yeah.

Jennifer Drake: I think one thing that I always stout in the. I use the word consult cautiously because it's really just a little bit more about drawing on the experiences and guiding, um, and the realities. I think the piece that's so important is all the time in the field. It's the realities of how it faces the customer and how the salesperson interacts. Those are things I've lived. I've walked in those shoes and being able to work side by side. There's many, many challenges right now happening in retail. And I think being able to come at it from an angle of, I've done that, I've operated the business. Let me help you. It. It just feels authentic to me. Like, let me help. That kind of is really why, you know, I wanted to do it.

Host: Yeah. My wife, I. I hear these stories because my wife is in retail, and that's what you and I connected to that. And she tells me these stories, and I'm thinking from a. From a different level kind of a thing. So what? Couldn't we do this? Couldn't we do this? She's. They don't want to hear that.

Jennifer Drake: They don't.

Host: It's the blockage is there in a lot of cases, you know, in doing that. So, um, you talked about your father starting that business, and that was kind of a inspiration to say, not at that point, but later in life said, you know what? I could do the same thing. I can go online and create an LLC in 20 minutes. That's when it could be done. And you start from there.

Jennifer Drake: Exactly. Um, you know, I think you. You often look back in your journey and you think about the things that have shaped you, um, you know, and the values of who you are. Um, and I know that, you know, companies put values on the wall and, you know, therefore, real reason, all that. But when you think about the people that have shaped you. If we go back to kind of the lesson of my dad, um, my dad was the person who kind of inspired me to have resilience. He was a veterinarian, um, and his path, like we talk about not being straightforward was not straightforward. Um, he wanted to be a veterinarian, but he couldn't get into vet school. And he applied year over year, so he had to do something. So he decided, after going to college, I'm going to go to law school instead. So he starts law school, and he goes and he completes two years while in the backdrop, still applying for vet school. And he says, you know, finally, he gets accepted. He gets accepted to vet school. He's just completed his second year of law school, and, you know, you're nearly two years in. What do you do? You know, it's logical to just finish law school. Yeah. But his heart said, that's not what I want to do. So he took the hard path and he moved to Georgia. Um, and I think my mom threatened to leave him, although she didn't, thankfully. But they took a big leap of faith. And that taught me. And that story sits with me, uh, you know, about resilience and tenacity and courage. Um, I always, you know, look at that, and I think I can pursue the things that are truly meant for me, even when the path is not practical. And I think I inherited, in trying to do this business, a lot of that from him. My. My career, like I said, hasn't been linear. And I've had these moments where you got to say, am I going to take a risk? Am I going to bet on myself? Or, you know, am I going to be traditional? And I think that lesson that my father taught me, sometimes the right path is the hard path, is a lot about pairing passion and discipline. Uh, and so, you know, when I think about building Avenel Field Group, um, I think about, you know, resilience, the courage, the service, and the willingness to keep moving forward even when the path is uncertain.

Host: Yeah, it's amazing how these small things happen when you're growing up and going through these challenges that you look back on life and say, oh, that was a building block. That was a building block to make me think a little deeper than what I was doing. So as you were talking through that, I. We've had people on the show that were lawyers that are no longer lawyering. We have. We've had doctors who were no longer doctoring. They're doing other things because they felt the passion was someplace else. And for someone that was in law school, second year, and you came up with this brilliant idea, you tell your family, say, you know what? I'm going to quit. Quit school, and I'm going to go become a vet. Yeah, I can imagine the look on that. Because, you know, when you talk to your family about things, is he crazy now that we need to call someone in? Because something is happening? But it was a lesson learned that you were able to build on, um, from so small moments.

Jennifer Drake: Yes, yes. That one. That one was definitely, you know, would stick with me. And I think my dad thought that was no big deal. Um, you know, when I. When I recently kind of shared that story with him about starting my company, he kind of was like, oh, you remember that? You know, kind of thing. And I was like, dad, like, I don't think everyone has the courage to have the pivot, you know, and not to mention financially, let's be like, you know, you know, life is expensive. And so I think learning how to navigate, you know, I have two young, young children that, you know, you try to figure out, well, can I really go do this? Um, so, yeah, I think it's. It's. It's intentional risk taking, as my dad described. Um, but, you know, it's. It's exciting and it's energizing.

Host: Yeah, it is. And so. So what do you do for those moments? I mean, you feel good, you're moving towards it. Avenue Group is starting, business is coming in. But you still have those moments when you're thinking, uh, you know, I. I just got back from Dubai a few weeks back because of what's going on there, a lot of things on hold. And, yeah, I wake up in the morning and I log in and they said, uh, the project we're working on that was supposed to start in two weeks, we're going to put that on hold. Another project, I had a project I was working on in Mongolia, and I said, oh, I've never been to Mongolia. I can go to Mongolia. We're going to put that on hold because we're not quite ready yet because of. So how do you deal with those? I don't want to say Setbacks. But how do you deal with those stumbling blocks?

Jennifer Drake: Yeah. So, you know, I think what turned into. And, you know, people look at my resume and have a lot of questions about, you know, why this, why that. Um, you know, for me, it kind of. The more recent days, I took a more intentional pause. And, you know, I think I thought that intentional pause would pivot back quickly into a traditional role. And, you know, what I learned quickly was the job market and the world like you're describing isn't necessarily recognizable, even from three weeks ago.

Host: Yeah.

Jennifer Drake: And so I think that's where you begin to dig into the resilience or kind of the grit that you build. And you kind of have to decide, okay, this path is kind of could go left or right. What am I going to do? Did I expect not to be working in a formal. Formal role in this moment in my career? Mid career? No way.

Host: Yeah.

Jennifer Drake: And so those building blocks, you know, I think you keep putting them up and taking them down and moving them and shifting them. And I think all of that. I know I've said the word resilience four times, but it defines you.

Host: Yeah. You know, I. What you're talking about is life.

Jennifer Drake: Yes. Life is life thing.

Host: Uh, life is like. Life is like. I love that. I'll send you a residual check when I use that. Life is life because, you know, especially for young people today, and every time I see these notices that, because of AI, they're going to lay off so many.

Jennifer Drake: Yeah.

Host: And I respond to it. And I respond to it. Uh, and I don't want to say a negative way, but I respond. These are people's lives. So you say 2, 000 people are going to be. You've affected 4,000 people. You've got wives, husbands, families, mother, father, taking care of all these kinds of things. Could we give a little more thought to this as opposed to showing a headline that says 4,000 people? Yeah. Because eventually you're going to get back on track and say, no, I don't like the way you did whatever you did.

Jennifer Drake: Yep.

Host: So sometimes when I'm in these so, uh, called board meetings with these so, uh, called big shots, the key about being independent is I can say exactly what I want to say. Within reason.

Jennifer Drake: Yes.

Host: But I want you to understand from our side, the discussions that we're having.

Jennifer Drake: Yeah. I think that, you know, when you say the headlines about the layoffs and everything, um, I really kind of carry that with me very, very closely personally. Um, you know, I think one of the things that I think about in my career, with retail having gone through so much change, one of, I think the toughest lessons comes in the staffing changes or the organizational design that you have to own. And I've sat in that seat where you're in a room thinking about what to do and how to evolve. And so, you know, as you're talking about leadership lessons, right, they come in all shapes and sizes. M. Um, you know, so, you know, I'll share, you know, in terms of leadership lessons, I think, you know, when I think about a small leadership lesson, um, and a big leadership lesson, you know, something that early on in my career, I'll never forget, I had worked super duper hard. I was a department manager, um, and growing through the ranks of leading bigger departments than, you know, more employees. My first employee leadership job was three employees. Then it was seven, 10, um, and I was, you know, up to 85 employees. My biggest department manager job I had had in the beauty division. And I remember thinking, I'm so prepared for this job and, you know, getting there and it not going quite as I expected. And I'll never forget, you know, my store manager sat me down at her kind of round conference table and said to me, you know, very directly, are you flying the kite or is the kite flying you? And I was like, that was this moment, this dagger of, like this tough conversation. And, you know, I had to kind of digest that. Um, and, you know, some of these tough conversations aren't always bad. They can be tremendously helpful. Um, but back to what we were saying around layoffs, the big. The big lessons. You know, one of the large lessons I've learned is having to lead staffing reductions or organizational changes, especially post Covid. And when you're sitting in that job where you own the P and L, and you have to look with honesty at the business and say, what model are we looking at to build in the future? Customer behavior's changing, digital's accelerating, cost pressures are increasing. Those economics are real. And I think decisions that you're describing require a lot of discipline. And I think you can sit and look at the data, and I appreciate the data, and you can look at the labor models and all of that. But when you ask yourself, where are we going to invest, what bets are we going to make, and how are we going to get a return? The hardest part of that is labor is not just a workforce management tool like you described. It's people, it's somebody's job, it's their family, it's their routine, it's their sense of security. And, um, what I've learned is the balancing between those two things. And you have to be willing to operate differently when business requires it. I would say being scrappy or agile and trying different things is important, but sometimes the answer isn't as simply less payroll. Um, you know, and I think people also appreciate when you have to make tough choices. One thing that sticks with me is that telling people why. If you can't stand up and look people in the eye and describe why you've made the decision, then don't make the decision. If you can describe why, then they'll trust you. Okay. And those moments really require courage and humanity. And I really believe the health of any business is about communicating with honesty, you know, treating people with dignity and helping people move forward. It's not just a headline.

Host: That's, that's powerful that you talked about that. Um, I love the kite. That's another one. I'll send you a residual check when I use that. Ah. Um, I gave, I had a perfect audience because I mentioned I was in Europe a, uh, few weeks back and I had about 500 people, people in attendance. They were CEOs, they were government officials, and they were educators as well as workers. And when I understood the audience, I said, what is my why statement? I call it my why statement. Why would I talk to these people and what do they need to know from my side? And I talked about this intersection is coming, the technology people's impact that you're having, schools that are, uh, graduating people that they paid 100,000 plus for a degree. That's basically, and I'm saying this in a nice way for educators, that's basically useless because I can find someone else to do it as a startup, is that you're in charge of all of this and how are you going to make all this work? And everything you said tied back into that. So if I use the kite analogy, who's flying the kite? You're supposed to be the big shots in this country that's flying the kite. But the kite's kind of flying you. I love that.

Jennifer Drake: Yes. Yeah, that one stuck with me. I thought, am, um, I going to lose my job or am I going to go pivot and figure this out?

Host: Yeah, I love that. I love that. So how would you describe your leadership style today? So you've gone through from the Nordstrom says, first, getting into this understanding from your parents and the pivot your father made to do, followed his dream and doing that, and then getting inside of the so called elevator, Elevator goes One floor, two floors, and there's promotions and all those kind of things. Exit, get off to this floor, and then you got to figure out which elevator to get on for the next side. So you think, when you think of that, how is that change your leadership style?

Jennifer Drake: Yeah, I think, you know, early in my career, um, I was very hands on, very execution focused, very close to the work. I think people probably call that a micromanager. Um, and you know, I wanted to solve problems and make sure every detail was right and prove I could drive results. The keyword early in my career was probably. I, um, and I learned very quickly that success doesn't come through. I, it literally comes through. We, um, and there's a lot of value in doing the work, don't get me wrong. Being close to the work, it taught me, Pace taught me standards, accountability. Um, it taught me what great execution looks like. So I still believe in staying close to the business and the customer. But my leadership style has definitely, definitely evolved. Um, today I would probably describe myself more as a strategic, empowering and people centered. Um, I still have very high standards and you can ask anyone who I've worked with, but I'm more focused, I think at this point in my career and building clarity, um, alignment and I think people being around me with great capabilities, um, I've learned big time that the goal is not to have all the answers. Um, the goal is to create an environment where leaders can make good decisions, teams understand why, and everyone's moving in the same direction. So earlier in my career I probably led more through energy and execution. Um, but today I would describe it more as clarity, you know, building trust, giving context and empowerment. But the core, I would say of who I am hasn't changed. I still care deeply about people. I still move with urgency. I still believe in high standards. But I've learned that sustainable performance comes with building leaders, not just driving activities. And I think that is a very, very different way that my early twenties

Host: leadership all bright idea bushes.

Jennifer Drake: Oh, yeah, I was in it.

Host: Okay, step back, step back. Um, the impact that you had, and we mentioned this offline, was the fact that when we did our marketing piece a, uh, day did the marketing piece, I saw a lot of people that I know from off Sacks through where my wife worked until they did what they did and were commenting on this particular show. I see Michael Calderon is. Michael lives right up one town above me. He's listening in morning to you both. Patrick McAvoy, um, I assume probably in the retail business and then normally Gary Bland Is here from Atlanta, who listens in every week. And Peter Piccinini started out in. Well, started out in Broadway and is now wealth manager. He manages all these wealthy, wealthy, wealthy people. So I'm not in that group, but he's. That's. This is what he does. So we all take these kind of things that happened in doing this, but it showed the impact because normally when we do the pre market, who's coming on? I see all the clicks, and I look at the clicks, I look at the background, and all of our people were in redo. So you made some impact. And people said, well, let me listen to this to see what, how she's been doing and what is, what's going on, you know, so it shows that. So the question I was getting to was about coaching and mentoring future leaders. And you're working with people that you've worked with years before. I told you the story of the young lady who'd made vice president and how we had gone through, and this was 20 plus years ago, and we still kind of connect in doing that. So walk us through the importance of giving back and pulling the next generation of retail innovators.

Jennifer Drake: Yeah, no, I think that's the most special part about what we do. Um, giving back through coaching, I think, has always been one of the most meaningful pieces for me, whether it's formal or informal. You know, there's great examples of formality. You know, I, you know, in the video you saw that was for actually the, the National Retail Federation. And I looked forward every year to going to that big show in Manhattan, but not to see all the people at the big show was to see the executive students.

Host: Yeah.

Jennifer Drake: So I used to go and do the, you know, executive mentoring program for about five years in a row on a Saturday. And I loved that, you know, had the opportunity to meet all sorts of people. So.

Host: But.

Jennifer Drake: But that's a formal mentoring. I think a lot of what you're describing is staying connected and available. And sometimes I think people, um, really need you in those moments. Um, they have someone that they need to talk to about something. You listen, you help them make sense of maybe what's happening with them. Remind, um, them about their strengths. I think everybody needs a reminder, but it's a big part of how I try to give back and help people see kind of the bigger picture is kind of understanding what might be coming down the road for them. Um, I think this is actually a very positive part of technology. You know, the text or the call. I mean, just this morning, you know, really early in the morning, um, I got a text from um, somebody I worked with in the industry and it was, I hadn't heard from him in a long time. It was one simple emoji, it was a muscle emoji. And you know, he says to me, you know, go get it. And just that moment of connectivity and encouragement. What moves you? Um, and really in this next chapter, you know, as I'm working on Avenel Field group, it gives me another way to do that. You know, it gives me more reach to do that to more, with more people that they can succeed. So I think mentoring is everything.

Host: Yeah, I'm glad to hear you say that because the old model of I have all the answers, you know, come to me because I solve everything as opposed to going to them and saying this is what we need to do. Help me as so called leaders solve that. If you were. So I'm going to flip this and I'm going to give you a keynote session that you're keynoting a group of retail leaders. So you've got all the big shot leaders of all the retail groups. What would be a couple, two, three bullet points that you would give to them as about this new world of work, this new world of retail?

Jennifer Drake: Mhm.

Host: You could share a couple of key points that you don't want to leave them with.

Jennifer Drake: Yeah, I think there's a couple of things that I think about in terms of just basic principles I think is what you're describing. Um, and they're probably more simple, you know, so you know, you're not going to need a lot of paper to write these things down. But I would say if I was, you know, out there speaking, you know, to a broader audience about kind of what's guided me, um, part of it would be, I say number one would be like stay close to the customer. And that could be in any format. You know, retail, of course the customer is easily defined, but whatever business you're in. But like, you know, as I draw from retail, the customer tells you the truth and they tell it to painfully quickly, immediately. Um, and a strategy that you build only matters or translates into a better experience. Experience if in fact you are, you know, it's showing up with the customer. Um, so I think staying close to the customer would be the first thing. I think the second thing would be staying close to the field or the people. Um, I think it goes back to, you know, what drew me into Nordstrom initially, you know, in college, was this idea of the inverted pyramid and the fact that you Know, the customer is top of the organization, and the CEO's the. The bottom. And the people closest to the customer know what works, um, and what isn't. Um, and the store teams and the field teams are going to tell you where there's friction, where there's opportunity. So just, you know, be close to them. Uh, I'd say the third thing I would tell a more broad audience is clarity drives execution. Um, teams really need to understand priorities. Um, if everything matters, nothing matters. I think lots of people say that, but it's really true. And a big part of, you know, leading or, you know, being successful is simplifying complexity. Um, you know, so the teams can focus on what moves the business. And I think advice early on would be, you know, keep it simple. And then finally, I think one of the biggest lessons I would want, you know, broadcasted out there to just people starting out would be that performance and culture, those two things are connected.

Host: Yes.

Jennifer Drake: Um, you know, you can drive results for a period of time through pressure, but it's not sustainable. Um, and, you know, performance comes out of trust, it comes out of accountability, it comes out of development. So for me, I think, you know, thinking about operational excellence and customer experience, they're not separate. They create consistency, you know, to allow great customer experiences to happen. Um, and great customer experiences give operations purpose. So, you know, I think while those things sound, you know, simple, you know, customer field, um, you know, simplicity and clarity, I really think it is. If I could start off in my career now, like, then and know those things, I think it would save me a lot of heartache.

Host: Yeah. My wife told me a story the other week. Uh, this is back during the time that she was with off sacks. A customer came in. She knew the customer worked at another store, was looking for a certain size. She couldn't find it. But over the period of the day, my wife found it. And over her lunch, she walked over to this store and told the woman. And the woman never forgot she worked for a competitor, I'm gonna put it this way. And she never forgot that. And when this whole thing started about whatever it is, she was the first person to call, because she made that impact.

Jennifer Drake: Yeah. I gotta tell you, as I was thinking about being on your show, one of the first things I pulled out were a stack of all these customer service letters that I got from, like, what you're describing. And I read them all, and, you know, I think one of. I'm laughing because your story about Janetta, your wife, on finding the item one of the customer Service letters was sent to remember the brand. Brand Fasanab.

Host: Yes.

Jennifer Drake: Yeah. So I helped launch in, in the store. I was the manager of that department and you know, it had its own boutique, so it drew in people that, you know, oh, wow, Nordstrom's gonna carry that. I mean, Nordstrom was one of the early, um, retailers to carry, you know, coveted brands that, you know, had their own business. And so I'll never forget I had a customer who came in wanting this very specific item, just like your, your wife is describing. And I worked for days with the buyers trying to track this item down. And the letter that, that, that individual customer wrote, and this is back probably in 2003, um, they wrote to Blake Nordstrom and said, I want you to know that this individual salesperson in your store in White Plains tracked this item down for my wife. And those are simple things. So as you just described, the same thing with Janetta. It's absolutely kind of about that.

Host: It's about that. It is about that. And I think as we select leaders of, to move into these positions, that's one of the things going to look that. Because you could be the excellent buyer, you could be the excellent, whatever it is in retail. I don't know the job families, but, but do you have the people skills to do that? The people skills is going to impact org health. So that's my kind of new thing. And talking through that is that organizational health means that we can meet all of our KPIs as a result of that. And one of the things that I, I have been learned and talking through from my side is that I kind of envision myself as a workforce architect. And all that means is that you come to me with a plan of the house you want, the building you want, or the strategy you want. And I'll build a people strategy to that. And I think even for retail, you know, when you think of the stores you're opening, you need to make the people on the floor. Those are the people that's going to make that impact of looking for that dress and finding those things and, and putting it all together. Yeah. So, um, how do you stay ahead of what's happening today? Because, you know, I, I get up and I, I post articles to read. I'm going to read it later. I'm going to listen to a podcast later. That's just my style.

Jennifer Drake: Yeah.

Host: When I travel, I have a booklet of all the stuff that's printed.

Jennifer Drake: Yeah.

Host: I'm going to kind of flip through. How do you stay ahead of. Because retail

Jennifer Drake: yeah, Staying ahead. Wow. That's. That's something that's changed a lot over the last couple of years. Um, I would say my approach is just continuous learning and staying curious. Yeah, of course, I, you know, I read, I listen, I flip through the, you know, Instagram, all that. But I think paying attention, um, comes from, you know, going back to this idea of being close to customers. Um, I try to stay open, um, to things as pretending I'm a beginner. Um, it's not always easy when you have a lot of history in the business, but consumer behavior is changing a lot. Technology is changing a lot, and you can't assume what worked five years ago is going to work now. I tend to ask, and my teams out there, who I've worked with, know this. I ask a lot of questions. Um, you know, what is the customer responding to? Where is their friction? You know, things like, what are teams struggling to execute? You know, what. What are younger leaders seeing that I'm not seeing? And for me, I think staying relevant is about kind of combining experience with curiosity. Um, experience can give you a pattern recognition. Like, you can identify it. But curiosity, I think, keeps you from getting stuck. Um, and in one of my most recent roles, you know, working for Gap, Inc. Um, I had the great privilege to spend a decent amount of time with Richard Dixon. And he is, you know, just fascinating and intelligent and, you know, all the things. And one thing early on, and he's repeated it over and over on store visits, was what if and why not? I mean, anyone that works at Gap knows that saying, and he's right. Like, what if, why not? And, you know, I found myself repeating that over and over. And so I think it comes back to saying to your answer about. To answering your question about just being curious and challenging your own self to say, like, okay, that worked for me then, but maybe this is not going to work today.

Host: M. Well, let me just say this to you. Um, what if? Why not? And then I'm going to go back to the kite. I'm going to write an article probably this weekend on the kite. Because that clicked a lot of things with me. And my way of doing what I do is to. If I feel it, I'm gonna write about it. I'm gonna put it out there to see what it is. I will tag you because you were

Jennifer Drake: the founder of I'm passing it on. That was you said to me, you know, and I think there's. There's one point I want to make while you're saying that is stories. Um, how many times did you hear a story, then you told a story? And, you know, I think that is. Comes along with the culture of, like, people. And, you know, you know, I think about that story on the kite, right? And. And I'll tell you, it was my store manager when I was at Tyson's. And, uh, you know, she probably had somebody say that to her. Who knows? I don't know where she got it from, but I told that story to somebody else. I'm sure I used it. And so I. I think stories have a way of giving.

Host: I'm gonna give it a global context

Jennifer Drake: and make sure she knows it's her.

Host: And I'll tag you. I'll tag you. Uh, Jennifer, thank you so much for being a guest on the show. I know we're running a few minutes over because we know, we try, but it was so much. This could have gone on and on because you've dropped so many interesting nuggets of. Of. Of what life is about and what careers is about. And this was the reason behind starting the CEO series. Not to just talk about, you know, this polished version that you see here. What happened as you made that trip to that. So, to everyone who joined us today, thank you for listening. Uh, we'll be back next Friday on another journey, because behind every title is a story we're telling. And if you've listened to this conversation, what we have to offer every Friday because. Because she brought her A game to us today. The A game to us today. Jennifer gave us. Gave it all to us. I've got three or four notes that I'm going to work on a little bit later, so I need you to hang on for a second. Do you have any closing thoughts that you want to leave the audience with?

Jennifer Drake: Yeah, I mean, I would just say that, uh, my closing thought would be that careers like you described rarely unfold in a straight line. And that's not a bad thing. You know, my own journeys had twists and turns. Each part has taught me something.

Host: Yeah.

Jennifer Drake: Um, you know, I think it's taught me that leadership is deeply human. And as I move into this next chapter, you know, through my life, I feel grateful, you know, for the experiences that shaped me. And I'm still very passionate about helping people. But if there's one message I would leave people with, it's trust. Trust your path or trust the process. A good friend of mine has been telling me that more recently is trust the process. And, you know, stay curious. You know, stretch your opportunities. Remember that the most meaningful impact you leave is also to through the people who you grow along the way. And it's not just about you. And so I really appreciate you being, you know, tenacious about having me on this conversation.

Host: I wasn't going to give up. I wasn't going to give. I just want to do a quick shout out. Jody. Hey, Jody.

Jennifer Drake: Hey, Jody. It's good to see you.

Host: Scott. Hey, Scott. How are you?

Jennifer Drake: Great folks. So talented.

Host: Great folks. Great folks. Great team. And I've met all of the. I've met all of you through my wife, Janetta. She was the. The best person on the planet. So thank you, everyone. Scott says, always the A game. Always the A game. Okay, cool.

Jennifer Drake: Hey, don't apologize for a high bar. That's another one. Everyone would tell me, isn't your bar too high? And I'd say, no, no, I don't think so.

Host: Yeah, yeah, we're good. Okay. Thank you so much. On. On Wednesday. Hold it for a second. Yeah, thank you so much. We're going to close it now, and I'll talk to you offline for a couple of minutes. Take the CEO series with you anywhere, anytime. All episodes are now available on Apple podcasts, Spotify, and major streaming platforms. It's not just an interview, it's a masterclass in leadership.

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