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Jason
Should you accept mediocrity?
Jenna Habayeb
People are more motivated and excited when their leader is motivated and excited and hungry.
Sherene Aubert
Because when you're driving a team up a mountain, it's not easy. And you want them to not get distracted. You want them to stay focused.
Jenna Habayeb
And then I spent five years at Ipsy, grew the business from 300 million to a billion. I've now moved into my first president role. Now at Posh Peanuts.
Jason
Everyone talks about community, but do they really do anything with it? Welcome to the Operators podcast. My name is Mike Beckham and we are proudly brought to you by Fulfill. Aftercell Rich Panel North Theme Sarah's analytics and Postscript without further ado, onto the pod. Dealing with big box retailers means EDI connections. And that's often a trigger for needing an ERP system. We've been using EDI connections to Costco forever and the only way that we've really solved that problem to make it seamless is through Fulfill. EDI adds complexity to everything you do and Fulfill solves that complexity with their connections to their systems. You need Fulfill to move from being just a D2C brand to being a true multi channel brand. Because big box retailers are going to require you to connect to their systems using edi. Let me tell you, it's way easier if you do it with Fulfill. Hey everyone. Welcome to the Operators podcast. We have an awesome episode for you today. I am sitting here with two of the coolest women in e commerce, incredible marketers. I'm psyched to learn a lot. Today I have the one and only Sherene Aubert, a woman who actually turned down a job at Hexclad. Can you believe that? And then we have none other than Jenna Habayeb, who is the president of Posh Peanut. She is a CMO that has gone to president and we are stoked to have her on the Operators podcast. What's up, women? How you doing?
Jenna Habayeb
Doing amazing.
Sherene Aubert
So, so glad to be here.
Jason
Shereen, you've been on a few times already. How is this your second, third? How many times you been on?
Sherene Aubert
This is my third and I'm actually very excited to be here as your honorary co host because Jenna and I actually work together in a, in a capacity. I have the privilege of being able to support her at Posh Peanut and she is one of the, like you said, coolest, smartest, most accomplished e comm marketers, presidents, business leaders. So yeah, I, I have a behind the scenes look at what it's like to work with Jenna. And yeah, I'm, I'm excited to dig into to her background.
Jenna Habayeb
I don't know. I don't know if you want to see behind the scenes of that,
Jason
Jenna. I mean, your story is. Is awesome. Why don't you just give us a couple minutes on that and then I'm going to pop into a couple questions that we have for you today.
Jenna Habayeb
Yeah, I mean, yeah, likewise. So thrilled to be here. Love being surrounded by such great leaders and marketers. So I'm fangirling on this side as well. Yeah, I have a little bit of an interesting career background and excited to kind of chat with you guys because you guys are also in the thick of marketing. I actually came from an agency background. Spent years at some of the bigger agencies like Ogilvy and some smaller boutique agencies. Made the leap in house, went to fashion brand Splendid 7 for all mankind. Really was focused on building those brands, building out the creative, that emotional resonance with the. The customer. And then I took a brief stint into cannabis. If anybody ever wants to hear about the wild, wild world of cannabis, I can give you a million crazy stories. And then I spent five years at ipsy, which was probably the most incredible component of my career. I stepped in first as chief brand officer, expanded my role into full stack CMO, grew the business from 300 million to a billion. It was a wild ride. Super, super exciting and fun. Loved being in beau. And then I made a move into what we call like a CMO plus role. So almost like a chief revenue officer role at Ruggable. So washable rug brand. 500 to 600 million in revenue. E com first business. And most recently, I've now moved into my first president role now at posh Peanuts. So children's apparel again, E Com first business. So, yeah, it's been a. It's been an interesting arc. Not something I necessarily expected, but a wild ride so far.
Jason
And those are some pretty big businesses which, like, selfishly, I love talking to people who have worked at other big businesses because that's, that's the way to learn. Right. You've seen various stages in the life cycle. One of the things that you've talked about, which I think is interesting that people would. Would care about is this concept of the forgotten community Flywheel. Right. And everyone talks about community, but do they really do anything with it? You know, tell me about the forgotten community Flywheel.
Jenna Habayeb
Yeah, it's. We had a panel this week and we only had five minutes. I was like, what do I want to talk about that could be remotely relevant, especially with some phenomenal growth marketers? I'm like, I'm going to go with a little bit of a different angle. When I think about community, I feel like it's one of those levers that when I say forgotten, it's just sometimes untapped because we get into this world of growth marketing where we are just growth hackers at times. Right. And I am absolutely can be blamed here as well. Like you live in spreadsheets, you're building out forecasts, you're looking at attribution modeling, you're looking at CAC and how it's changing every day. You're thinking about, you know, channel diversity. And sometimes you just get so heads down in the minutia of performance marketing that you kind of forget to take a step back and say, okay, well what is it that's actually driving my business? And when I talk about the community flywheel, I really think of it in four facets. I mean, you obviously have your customers, which I'm sure we'll talk a lot about today. You have ambassadors, you have influencers and you have celeb and it's really about how you activate across each of those that then feed back into in. Great brands are highly engaging with their direct customers and community. They have really robust ambassador programs to get that awareness out there, to get the diversity of creative and content out there. And as you kind of like work up to then influencer and celebrity, each of these things attracts the next. And so it becomes this really nice flywheel where each of them is helping each grow. And so I talk about it a lot because, you know, I'm guilty of it at times too where it's, you're like, okay, how do I spend the next dollar in meta and make sure that it's, it's performing. But there's so much richness to leveraging your community to drive the business.
Sherene Aubert
And you've been at so many different sizes of business. I mean from Ipsy to ruggable to now posh. Talk about how that community flywheel scales at, at those different sizes.
Jenna Habayeb
Yeah, I mean, I think what I always think about is there's a very similar playbook in how you activate the community. It just really is at a different scale and also at different budgets. Right. Like I, I think about with smaller scale businesses you really have to start. I, again, I think of it like an upside down pyramid a little bit. You have to start with the customer and your community and then like ambassador and kind of go down. If you try and do it all, you're not gonna have enough resources or Budget to do it right. Smaller businesses, tighter resources, tighter budgets. What I see with smaller businesses and I think what really attracted me to posh and what I see now firsthand, sitting in this seat is really engaging with your community. Figuring out ways that you can grow your community and customer base helps drive the business and it helps attract that next ilk of customers and ambassadors to come in. And I find that some of the things that we've been doing that are really working is deeply connecting with our customers on our Facebook group. Shereen I mean, you see this firsthand. We'll have weeks where I'm like, oh, it's a little softer than we expected. Her and I go back and forth and like, should we spend one more dollar in meta? Should we push into another channel? And we're like, wait, let's pause, let's do something with our community. A good example of this is last week we had a couple soft days and we're like, all right, how do we get back on track for from a forecast perspective? And we decided to do digital Easter eggs on our site, which every other hour we were dropping clues on our site that we only fed into our Facebook VIP community. We saw almost a double digit growth in that day from a forecast perspective. And so it's like that's one example of how we're engaging our community. And so I think that how big
Jason
is that Facebook community?
Jenna Habayeb
250,000 people. So it's not, I mean, I'm used to ipsy. We had 20 million people in our community. Like, it's like such a different scale. But the reality of being able to engage and have your customers react in real time, it's pretty unbelievable. You also have to think about how engaged this community is. This is. These are moms, right? These moms are, they're on it. Yes. They're in love with certain brands. They know when there's going to be a deal. They know when something new is going to drop. They know, like we, we always joke about, we know if we're going to have a really successful launch, we drop every, every week. We know we're going to have a successful launch because we see gift card sales go up because people buy gift cards because they can preload their, they can preload it in Shopify so they can order right away. So it's really interesting to see like how engaged this community can be. And so, yeah, I guess to answer your question, shree and like, for me it's about, you know, you have to know what you can actually activate in the organization and not bite off more than you can chew. It kind of goes to even paid media. Like don't do every single channel in the world. Like if you only have so much budget, like focus really, really narrow and, and go go deep in those, those channels. And so for me I, I think about starting with community, ambassador and smaller scale businesses and then you can start ramping up as you have like resources and budget to go into other avenues.
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Sherene Aubert
This Posh peanut business is, I don't think I've seen anything like it. Like the rabid fandom that this business has is like bonkers. Like these people go insane. There's like a resale market. People will like buy up the stock, they will sell it out. They will, they'll have these massive like seven figure days when they drop a product. Yeah, like how, how did the business, how did that happen? Like how did they get to that point?
Jenna Habayeb
I mean all of this is Fiona, our founder. Like she should be the one that's talking on this, not me. Like she's the one that, that made Posh Peanut incredible. I think one amazing product market fit. Right. It's all about quality, having a very specific, unique position in the market. You know, our brand is all about bold, maximalist, whimsical, playful prints. And it's in a sea of a lot of minimalist brands and so very distinct. But she is the type of person that has really cared about engaging with the community and everyone she hires, she is obsessed with making sure that they're engaging. And so she's in there, I mean, you know Shereen, she's in there every single day. She's sending us stuff. Oh my God, did you see this person just followed us. Oh my God. Did you see, this person just posted us and it's like, okay, like, how do we feed that into ads? How do we feed that into our site? How do we get more awareness of it? And so I think it kind of like, stems from the founder being so obsessed with engaging with her community. I remember she showed me a video where they made her dress up as a bunny rabbit, and she just, like, showed up to someone's Easter party and surprised and delighted them. Like, she does that kind of, like, fun, quirky stuff. And I think it authentically resonates with the community.
Jason
So I want to get into a couple topics. First, I want to talk about this transition that you've had from, you know, being an agency person to an operator and a cmo, because I think there's a lot of people out there probably in your. In your shoes, that. Where you were. And then I want to get into some data analytics, AI, because that's an area that I'm really focused on. It's funny, like, you mentioned community, and a year and a half ago and two years ago, I was all over community, and like, different things come up and you wind up, like, just going down, you know, like your focus changes. And I'm just. I just made a note that I need to go harass some people about community here, here at Hexclad, but there are so many people that, that care about the pod, who are agency people and learning from great operators. Like, the two of you. Let's just like, backtrack a little bit into, you know, your agency work. Like that transition, how that prepared you. Let's just, let's dig into that a little bit.
Jenna Habayeb
Yeah. You know, I think the beauty of being on the agency side and anybody who's in an agency or has been in an agency really prepares you because you just put a lot of sweat equity into it. Like, I mean, I think about young years and agency, you have to be on top of every single trend. Like, you are the group that is bringing new ideas, innovation, pushing the boundaries for your client. And so I feel like you have to be ahead of all those things. And so you deeply immerse yourself in all the new things that are. That are coming about. And you have to dig in and really understand the customer. And so for me, I think the two things that the agency world really prepared me for were, one, being able to understand, spot the trends and do the. Do the homework to understand, like, where should you participate? How can you kind of push the boundaries from an innovation perspective? And the second thing for me is really the art of brand storytelling. Right. Like, I think being at an agency and having to have the most crisp, brief, right. Who is your customer? What are we articulating? I mean, these are millions and millions of dollars of your clients money that you're spending. How are you creating really sharp messages that resonate deeply for me, that really helped me as I moved to the brand side to be able to articulate and build out crisp brand identities and brand architectures. And so I think, I think those are the two things I would take away. The other thing I would say is I do feel like I had a front row seat in the craziest time ever. I got out of college, went right into agency world. And this is when E commerce. I don't even know if you could actually buy products on e comm. Like, it was like just starting. It was funny. I was talking to somebody at my company last week and she was like, I didn't realize. She's young. I didn't realize that you. That Facebook, you had to be in a college. I was like, yeah, in the beginning you had to be in a college to get Facebook and then they open it up to the public. My first year in agency was the year Facebook opened to the public, where you didn't have to have a college email.
Sherene Aubert
Right?
Jenna Habayeb
And so think about that Facebook. Like, there's like no other social platforms. So it's like so interesting to have been in an agency where your remit is about finding, trend, finding, innovation, bringing that to the customer. And it's just in the rise of digital and social. Right. It was such an interesting thing.
Jason
So, Jenna, that's, that's like prepaid ads, right? So you're, you're very much like traditional creative side of agency, you know. And now, you know, the agencies are, I mean, they do a lot of things, but a big focus. You know, you hire an agency when you want to run paid ads, right? And, and then if it's a full service agency, they'll, they'll, they'll get you, you know, they'll do a creative for you too. Just it's, it's interesting how agencies have, have evolved and what I find it's almost like you need now you need two agencies. You need someone that's like a super creative side and then you need like implementation. Does that seem right to you?
Jenna Habayeb
I think long gone are the days of like one agency being able to do everything really well because of how bifurcated the channels are. Not only the platforms that we advertise in, but Also the channels. So like your wholesale business versus your Amazon business versus your TikTok shop versus your D2C business. And I also think a lot of those specialists aren't great at the creative side. But I will say some of the creative agencies need to get with it because you really have to think about the range of creative that will feed the channels you are driving. Like we all talk about, creative is the new form of targeting the amount of volume you need to be putting into these channels to drive the business. And I think sometimes I see some creative shops aren't able to really catch up to that. It's like, let's look at this big, beautiful, glossy campaign. I'm like, six images do nothing for me. I need 6,000 videos, images. They need to be with an iPhone, you know, So I do think you're. You're right in that. I just think it's like finding that right balance of what kind of creative really supports the business. I don't know, Shereen, you're. You're in the thick of it too.
Sherene Aubert
Yeah. And the bifurcation that you're talking about, like, people either come up in growth or they come up in brand. And I think that's what's so amazing about, you know, a CMO to CRO to president, like the ability to, you know, you know, like the future of the CMO role and the future of the really good operator. You have to be able to do all of it. You have to be able to understand the impact of paid and digital and you have to be able to understand the P and L impact and the inventory impact and like how creative works and how it brings people in and how to build a community. So that is like truly what it means to be a good full funnel operator and cmo. And I think, yeah, what, what we're seeing is that people are coming up in one side or another and it's really hard for the majority of people to kind of like stretch into the other side of things. And that's what's happening with, you know, agencies or like external vendors is, yeah, they can only be good at one thing. But I do think that's what separates the sheep from the goats, is like the people who can stretch into all of those things.
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Jason
Well, let's get it. Let's get into that. You know, the part of Jenna's career that I think is really, you know, interesting on, on that career arc where you sort of gone went from a CMO to CRO and all these different acronyms, whatever, like, it's just about doing the job. Right. But you know, at Ruggable, your. Your role changed and I think that this helps us pivot more into just like getting into data analytics. Let's talk about that.
Jenna Habayeb
Yeah, I mean, I, you know, started out agency, went into more of like the brand side of what a CMO was, right? Because we all know CMO means a lot of different things in a lot of different companies, right? You have cmo, cgo, CRO, all the acronyms. Like you said, I think moving into more of a Croat revenue ownership role. Where I got prepared for that really was at ipsy, because ipsy, I was really brought in to help them on the brand side. And I had an amazing, amazing founder and president who really helped me open up my aperture and start taking on more of the analytical components of the business and more of the growth elements. So I feel like that really prepared me moving into the role at Ruggable. On the Ruggable side, again, you know, majority of our business was E Comm. We hadn't even been in wholesale at that point. We expanded in wholesale by the time I left. And majority of our business was North America. And that fell under marketing. Right. And so taking that on, I think, you know, yes, there was the creative component of the business, but it was really about how do we drive profitable growth. And so I had to turn on another whole part of my brain and really focus on what we're going to be the levers for us to drive. How do we think about channels? What is the most effective way to drive this business and still maintain profitability. Right. And so I feel like that jump really stretched me.
Sherene Aubert
Right.
Jenna Habayeb
Because it's like Your creative brain and your analytical brain are very different. And so I spent, I'd say probably 80, 90% of my time really thinking about the growth side of the business, still keeping, you know, keeping involved in terms of the brand side. And so I felt like I was like over indexing on that side at Ruggable.
Jason
I think this is the key here to, to being an exceptional professional, right? You understood the brand side and you're like, whoa, I need to get, I need to get on the numbers, right? I need to become, I need to become a performance marketer too. And that's like, I think anyone out there that wants to be great, that wants to achieve greatness, it's, it's like when I was an investment banker. Investment banking is a combination of sales and marketing and execution. And like, investment bankers are the most elite B2B marketers on the planet. But it's a really hard job and most people sucked at it because they can only do one side of it, right? So you, what you did is you managed to go and like learn the other side, right? And you know, that was a lot of work. And, and you get into, you get into from like storytelling and what's cool and what's trendy or what's going to resonate with a person to like raw numbers. Like, how does this, you know, I don't care what the brand people say if my numbers don't make sense, right? If my numbers aren't working. And you, and like, you need the foundation as a, as a business to, to be able to make those decisions. And like on our side, I, coming from a finance background, I always understood the value of data. That's, I think, why, for me, the transition to D2C was actually pretty easy. But having the data that you need to make good decisions, whether it's like, you know, MTA information, mma. Mmm. Information. Just, just understanding all your metrics, your financials, like this is, I think this is an area that people need to take more seriously. And with like, with AI layered on top of like really good data, I mean, I think where the way we run our businesses is, is like being transformed right before our eyes, you know? What, what, what do you think?
Jenna Habayeb
I mean, it's like I feel like I'm back in that. When I was telling you, like I'm in the front row seat, I feel like I'm like back there again, right where it's, I think this is going to give people a much bigger advantage. Like the pace at which AI is helping people extrapolate Insights from the data, I think is going to make it easier for a lot of people that maybe are more nervous and, and, and concerned about getting into that realm. Um, look, the analytical side, it's daunting if you're somebody who comes from a creative. I remember the first time someone walked me through an acquisition spreadsheet and I was like, I'm good. Like, I think I want to go back to the photo shoot. Like, what? I have to look at this every single day. And then, and then you start seeing patterns, and there is, like, art to it, right? Like, you start seeing patterns, you start understanding, you know, what metrics to really look for. And I feel like, if anything, it makes you a stronger marketer. So, like, no matter either side that you come, come up, it's. It's like these light bulbs start turning on, right? I was like, okay. On the brand side, I'm like, okay. And then a light bulb turned on, I'm like, oh, wait. But I can make this brand side even more powerful by driving it through this. And now as I've even expanded my role more, like, more light bulbs are going off. I'm like, oh. But then if I had the inventory and the assortment at the right price, like, it all, like, I feel like I'm a cartoon character. Like, 100 light bulbs above my head that I feel like it's like, helps connect the dots. And I think the, the place that we are right now with layering AI on top of it is just going to fast track that. And I actually think it's going to help some people leapfrog it. You do need to know and understand the numbers, but I think it's going to make it a lot simpler. I mean, Shereen, Jason, think about, like, the spreadsheets you had to look at and now how easy. Even today, it's easier to really look at things than, I don't know, a year ago.
Jason
How are you guys set up to make all these decisions? Because that's the thing. The first thing you have to do is like, you've got to create the setup. You've got to set everything up so that you can actually do it. Right.
Sherene Aubert
I have so many thoughts on this because I, you know, I ran data at Bobby, and as a growth marketer, there's like, you can't do your job without access to data. And my exposure to different companies was, like, mind blowing how far behind they were at building their data infrastructure. The data infrastructure, they needed to actually make the decisions. Because like you said, Jenna, it's all Interconnected. And, like, yeah, maybe the growth marketers are looking at the data more closely because their job relies on it. But once you have all the data coming into your database and you're able to create dashboards and see how interconnected it all is, that's when you're really able to unlock real insights and drive the future. Because what data gives you is access to the past and access to what's currently happening. And if you can become really good at harnessing that data, you can actually not only predict the future, but create the future, which is, like, insane. And so Posh Peanut works with Saris Analytics. They're the ones that implemented the data infrastructure for the business. And that, like, you know, I almost want to explain it, like, everyone's five, because I truly think so many businesses are behind on, like, setting up their data infrastructure. But essentially what a good data infrastructure is is you bring all of your data sources through a process called ETL into a data warehouse, and then you can model that data and surface it in dashboards. And that's what Posh has. And it's. I mean, we were in a meeting the other day together, and there's a new dashboard that was built that basically, like, you know, we were.
Jenna Habayeb
We were.
Sherene Aubert
It's like we're all kind of explorers digging around in a cave with a flashlight. And then we build this new dashboard, and we're like, oh, my gosh. Like, this is. This is, like, what we've been searching for. Like, this is the answer. We all kind of knew what it was, but to see it here validated is, like, insane. And now we can make, like, real decisions, business decisions, to answer that question. And that's through. Through the work that the team has been doing with Saris.
Jenna Habayeb
Yeah. I think when I first came on, Posh had brought on Saris analytics, and we had worked really closely with them on, like, what were the priorities? How do we need to clean everything up? How do we also make sure that we could really validate all the data? Because we had a big mess happening behind the scenes, and they've done some incredible work to now get all the piping set up. And then I think that next step was really about how are we shaping it into either dashboards or specific models and projects that helped us make big business decisions. One of the first ones when I first came in that I think was at least groundbreaking for us to actually make very quick actions was we did not have a good handle on our inventory. And when. I mean, not a good handle. I mean, what Channels had what. What was old versus new. And we were sitting on a pretty big inventory problem. And it was the first thing that we worked with Saris on. And they were able to help us bucket and cut all of our data so that every week. And poor Shereen had to sit through this. But the first three months, I was like, we're pulling up the dashboard. We're pulling. Looking at every single cut. We are reading and reacting the business. Why is this piece not moving? Why is this not moving? What do we need to do? Do we need to pull things from Amazon? We put it back in, and it helped us, in three months, get into a phenomenal place with our inventory position. Because I think of inventory as capital. Right. That is dollars sitting there. That can be driving my business. How can I best use it to move the business forward?
Jason
And you have so much control over that. Like, you can't. I mean, just. Just knowing what it is and where it is. And like, there's. Controlling the buyer's purchasing decision is what marketers are trying to do, in my opinion. It's just like, it's much more difficult work than understanding and controlling your inventory. But there's a lot of dirty work behind the scenes that has to happen to get it right. But it's just. It's just very doable with the right solutions and the right effort. And that's. I think that's really one of the keys here. It's like, it should be table stakes for everyone to get this right. And it's amazing how often you hear about people having inventory problems. Your only inventory problem should be that for some reason, customers don't want to buy it. Right. And then you figure that out. But everything else, like, you should have complete control over. And that's essentially what happened for you guys, right?
Jenna Habayeb
Yeah. And I think I echo what Shereen says is, I've been in so many organizations, let's be honest, like, nobody really. I mean, maybe if you're a giant organization, but nobody really has it. Right. Like, I'm surprised to be like, you're an organization this big and, like, you still don't have your data shaped in a way that that's usable. And so I think it's really about, like, chipping away at it and not, you know, getting so nervous about the task ahead. And that's like, that's what we did. We were like, I. I came in, I was like, inventory number one. Like, we gotta get a handle on this. We need to leverage this. We need to get ourselves in a good Good position. I said number two, was working with Sherene, getting all the data we needed piped through all of her dashboards so that we could make real time decisions on everything we're doing. On the growth side, the third one that we tackled, and this is the one that she's saying we explored around in the cave, I love that analogy. Was really getting much deeper cuts on our assortment. We have a wildly complex assortment, right? We have collaborations, we have internal prints, we have all different size ranges, we have genders, we drop every single week. And so really understanding our assortment has been critical so that we don't get into inventory problems right now. We can be buying more sophisticated. We can understand how we want to design in the future. We know what drove the business. And so that's probably the third big leg that we've been working with Saris on. And yeah, we now have some really fun dashboards I've been tinking around into. I'm like, ooh, what happened here?
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Jason
So you get your data all in one place, cleaned up, which is a tremendous amount of work. Like, that's the beginning. And people don't realize that. And, and, but when you do that, it saves so much time because I just remember everyone trying to grab data from here, grab data from there, put it in a spreadsheet, manipulate a spreadsheet, the data, who knows if it's right or wrong. But there's just like so much manual effort, right? And you get this all set up and you have it all going. Then you have dashboards, right? Sherene's got got dashboards for performance marketing. You've got dashboards for all of your inventory. What I. What I want to do. And what we're doing is actually taking that to the next level with AI. And I don't want to look at a dashboard. I want to get a report. You know, I'm a, I'm a C level executive. I don't want to log in, I don't want to get it. We get a bunch of daily dashboard updates which are hugely valuable, but I want like the context to go with it. And to me, like, that's the next frontier and really fun. And I'm actually working on that with Sarah's is like I'm, I'm getting. I call it. And I shouldn't really give this away.
Jenna Habayeb
You should please. Because we're doing something similar. So please, let's. Can we all three of us share the tea. We're all trying to work on this at Tandem and we're all at different phases that.
Jason
Sarah's probably going to kill me for this. But um, when you do SEC filings, there's a, a commentary around the financials called MDNA Management discussion and analysis. And it basically brings the numbers to life with context, with, with a narrative around the numbers. And I'm like, this is what I want because I don't want to look at a dashboard. You know, I mean, I don't want to let's like, you know, be peering into a spreadsheet. Tell me what's going on. Like the, the, the system, we have all the data and then you have dashboards. But dashboard 2.0 is, is like really just like a narrative report. AI leverage narrative report that. So every, so every Monday I get an MDNA report which basically goes over all of our sales performance across various channels, across various countries. Marketing metrics that underpin it, new customer versus returning customer. And like I just keep adding more to this report and it's, it's, this is what I need as, as a senior executive. But you cannot do any of this if you don't have the data. And that's why we started the, the data warehouse project couple like a couple years ago.
Jenna Habayeb
Now you're, you're definitely ahead of us, but we're coming for you over here. So yeah, we're, we're also working with Saris. We've obviously now that Claude, you can leverage with MCP on top of your data warehouse. We're starting to really explore that because similar, right. I'm, I joke about, I call it spread spreadsheet sludge, but I have like 400 tabs open and I'm like, okay, what's Happening here? What's happening here? What's happening here? Like, all of that. And I, I really want to find a way to simplify this and how can AI help, you know, surface that for me, but also allow me to very quickly dig in. Like, you know, I don't want to have to go to Shopify or look into six dashboards and be like, what were the top selling products? What were the bottom selling products? Why did this thing move? What. Where am I breaking in my ages, right? Am I acquiring more customers at a younger age? Am I. Are some of my returning customers aging out? Like, I want to be able to get those quickly so that we can react quickly. And I know Shereen, we've been doing even some work. She, she has a Slack integration that kind of does that just on the marketing side. And I'm like, okay, now if I could have that in a broader view, that would be amazing.
Sherene Aubert
Yes. This is my belief about the future, is that everyone hates using dashboards. And yeah, having. Having been in data leadership roles at, at both Bobby and Ilia, it's like pulling teeth to get people to look at a dashboard. So being where the people work, like surfacing insights in Slack or sending dashboards in email, like automated, or even allowing them to chat with the data the same way they would a data analyst, you know, like tagging them in Slack and getting insights back, I feel like that's where the future is going and that's what, what AI is going to unlock. But, you know, we've all experienced this. AI data analysis can be slop. If you don't have the data warehouse you still need, like the data coming in, it's clean, it's modeled, and then you put AI on top of it. Now you have a data analyst that can answer you in five minutes.
Jenna Habayeb
Yeah, it's crazy how fast it's happening. That's what I'm saying. I almost feel like, I feel a little jealous, like all these people are coming into this business. I'm like, man, like, you're going to be in a place where you get to leapfrog this. We got to do all this hard work to get here.
Jason
And, you know, for me, it's like Sherene just said, not wanting to get in dashboards. As a senior leader, you should be getting information that this basically, like, sets off alarm bells in your head. Like, okay, this channel's doing well. This channel's not. What do we do? Right. It gives me the information so that I can go start asking questions. You know, you, you, you all are like maybe more in the tactical side of things. Even though Jenna, you're a president, you know, I think eventually organizations get so big where you as a leader have to have this information to just to be able to go to people and ask like, and, and then, and then you develop the strat, the strategic plan to, to make the changes that you need. If one channel that, that's the way I look at it. It's like we have our channels. It's like certain, certain channels I used to get great information about. Right. Because it's just there other channels I just, I just wasn't able to. So it just made it difficult for me to like really understand what was going on. Like my, my information was just like old. Right. It was just slow. So this is, this is, you know, doing this properly, having yourself, you know, set up diligently is just going to make you so much faster at, at everything you do. And, and if you're, and if you're not, if you're not able to speed up, like you're going to get lapped.
Jenna Habayeb
Yeah. And it is, I mean it's daunting. I think all of us, even the evolution of what's happening in the AI wars, it's like every day know I'm like, oh great. We were using this platform. This thing has changed. Okay. Now it's this one. And I think it's, it's really about, you know, where do you want to focus your energy and what's most important. And for me, this initiative of us figuring out how we can leverage AI on top of our warehouse and then building out the really key use cases for our team because you also have to train your team on how to use use. This I think is going to give us a really big step forward.
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Jason
Shereen, can you give us some real world examples, like about, you know, what you're doing on top of your data?
Sherene Aubert
Yes. Okay, so I'm experimenting with agents and what I really want to figure out is, like, how to bring more agents into Slack to do work alongside us. And I've been testing some with my team and I want to test more of them. But, yeah, we have our data warehouse, we have all of our data coming in. And then you now, like, the future of building software. Well, the past of building software is building software and giving users access to it. The future of building software is creating software, creating a data warehouse, giving an agent, like an API, access into the software, and then just interacting with the agent directly in Slack, giving it access to Asana, your project management tool, and having it do tasks for you. So that's what we're experimenting with is like, how. What are the tasks that AI can accomplish well enough that may need a human review? How can we get AI in our systems that we work in, not get a bunch of people to try and, like, take all their work out into an AI system, but get the AI into our systems and have them, like, actually execute on tasks? That is super exciting. I feel like that's going to be the future. And if you can arm every person with an agent, it's like giving them a junior employee or like an intern. They still, you still have to train it, you still have to tell it exactly what to do, give very clear context and instructions. Same way you would like a junior employee, but you just added an employee, a junior person to your team without, you know, with minimal cost. Yeah, that's the future. But I think it's all about having the right data, having the right integration with your systems.
Jason
All right, so, Jenna, I. I just. It's incredible to me. Incredible to me. Like, all these huge businesses you've worked for, like, ruggable. Ruggable was a juggernaut for a while, right? And then I be honest with you, like, I don't have young kids, so, like, posh peanut. Like, I'm just, like, blown away, you know, it's. That's the best part about the POD is like learning all these, you know, all these great businesses that are out there. And so how, like, how has your direction changed from rugs to rugs to clothing. Right.
Jenna Habayeb
Like, to beauty. I know. Beauty, fashion. Like, I've touched it all almost. I haven't done. I haven't done cookware yet, though. Home's close.
Jason
I know. Well, we, you know, we might be able to change that for you. But. But yeah, I think I'm. I'm super curious. We didn't dig deep enough into this, but, like, you know, what. What are the. What are the things that, like, translated well for you and then what are the things that you had to, like, learn along the way?
Jenna Habayeb
Yeah, I mean, I think most of the core fundamentals are there. There's obviously a lot of nuances in different businesses, especially with your distribution channels. Right. You know, working in fashion when I was at 7 and Splendid, you know, 50% of our business was wholesale. You know, another 25% of our business was our own brick and mortar. That's very different to manage and like a pure e comm business, it's just very different. Like how you invest dollars, how you think about marketing efficiency, how you think about marketing in general.
Sherene Aubert
Right.
Jenna Habayeb
So I think there. There is definitely some of that nuance and that, like, mental shift I had to make moving into other roles. I think when it comes to, like, ruggable, it's also. It was a very unique business model because the. It's made to order. Right. And so for me, the biggest mental pivot from, like, the actual physical product perspective from ruggable to posh, and especially in a president role with posh is the inventory piece. Right. With ruggable, you just had to buy raw materials, and then the rugs are printed. Right. And then they would go out. And so it's all real time. And so I always joked about, I'm like, if we did a Barbie partnership and we did a hot pink rug, if none of them sold, none of them were made. Right. Like, it's not a big issue with posh. If we buy 100 hot pink onesies and then sold, guess what? I have to deal with that. Right? So that was a big mental shift
Jason
for me from being a marketer to being a president. Right. And now just having, like, the view and the responsibility for. For all of it. And this is. This is actually like something that I. That I struggle with a little bit because we have a great growth marketing team and they're all super smart and they get the whole. They do get the bigger picture, but you do sometimes you're in your growth marketing silo and you don't realize that, okay, you want to run this type of deal. Well, what does that mean for inventory and operations? Like, someone needs to fulfill it. What happens if we do, you know, two different gifts with purchase and one just blows you know, blows out. And then it's like, wow, we sold 5,000 units of this, and we're not going to get any more for. For four months. And. And there's operational challenges to this. How was this transition from you? Was it easy? Was it hard? Like, tell me about that. Because I feel like that's a huge, like, leveling up in perspective to be able to say, hey, there's all this other stuff behind the scenes that we marketers aren't. Aren't doing and need to be aware of. And, you know, I think it's, you
Jenna Habayeb
know, in the beginning, it's. It's daunting, right? You're like, it's the same way as a brand person. Someone showed me the spreadsheet for acquisition. I was like, now I have to be in the spreadsheet. It's kind of like that, right? Where I'm like, now I gotta get behind the scenes and figure out what's going on with the assortment and inventory. So, you know, it's daunting at first, and then you kind of have to break it down and chip away at it. I think it's another one of those light bulb moments for me where again, I think about, oh, creative and brand. It was so sexy and I can make it really amazing. But now I know how the channels work and what works in the channel. So now I, I can make the creative better for the channels. Well, now I know the inventory and the assortment. I can make the creative better and the channels better to actually help, right? So it's like, again, I keep using those, like, light bulbs keep going off in my head. I think that, that it actually helps. So as. As daunting as it is to really unpack it. And again, there's so many nuances and complexity in our assortment. You know, a lot of what we've been working on, and Shereen, you know, she's here with us every day looking at it is, okay, well, we thought these things were gonna happen. We thought marketing XYZ was gonna really work. It didn't work. We didn't see the traction. What's the next best thing? Or we're seeing this ad take off, right? We. One of the things that we worked a lot on is how can we make our core business a bigger percentage of our business? And we have been hustling on the performance marketing side, hustling so well that we sold out of everything, right? And so we're like, all right, we're getting some good traction. We're bringing in younger audience now. How Do I maintain that on the inventory side? Right. And how do I make sure that we're buying into it? And so I think as hard as it was to dive into it, it's really allowing us to move a lot faster and figure out what needs to be put into the marketing funnel for us to be able to actually drive the business faster. One thing we talk a lot about is we have all of our launches. We have core products. We have key categories that we want to market. I'm like, I want to have a bucket of us focusing on slow movers, right. Things that we launched. That's just getting buried in the site because we're launching every single week that are great products. How do we, like, focus on those slow moveovers so I don't have to just move them into markdown and now have a margin hit? Right. So it's like, that's how I want us to start thinking about our assortment. Or as we're seeing, are there certain categories or styles that are really driving that new customer acquisition? What are they purchasing next so I can keep them retained? Or are there key products that are high ltv that we need to be putting more energy in as we're acquiring customers? Like, that's. I really. Shereen and I actually talked about it this week. I'm like, I want to be better dot connecting with, like, how do we leverage our assortment? Not just what we're dropping the creative and the performance channels. Like, how do we leverage our assortment stronger as a driver of growth?
Sherene Aubert
And you were at a massive apparel brand before that, drove a pretty significant turnaround. You were at seven, seven for all mankind. Um, you guys had six consecutive quarters of profitable growth after five years of decline. That's an insane turnaround.
Jenna Habayeb
Like, what?
Sherene Aubert
Talk about that. How did you guys drive that?
Jenna Habayeb
I think that, like, honestly, the biggest thing and this is. It was probably a good learning as I moved into the president role was operational efficiency. We had three apparel brands that were running completely independently, right? So three PD teams, three design teams, three marketing teams, three everything. Everything. And so it was about intentionally consolidating where we thought we could get the best operational efficiency and then keeping subject matter expertise, especially in the places of brand distinction and in design. Right? Like, those are the things where it's like, it made each of those businesses unique. So I feel like that was probably the best underpinning of it. And then it was really about building culturally relevant brands. Like, seven for All Mankind had been this premium denim brand, but it was so standoffish in a Time where the world was really rallying around inclusivity. And so we worked with not only the design team on making sure that our range of designs were more broad, but also even our size ranges, right. Like much more inclusive denim. Like this is the rise of good American that had, you know, much broader size range. And so we did that not only on the design side, but then also on the marketing side. So working with culturally relevant influencers, creators and like really bringing it, you know, into the modern age. So I think those two things together helped us really drive a more efficient business.
Jason
And that's really just spotting like the marketing trend really at the end, under, at the end of the day. So much of, you know, jeans brand, apparel brand, or almost, you know, any thing that's not like a durable good, it's just being, having your finger on the pulse and like a change, change is happening and how do we react. And if there's just a lot of businesses, like when you're, when you're smaller, you can do that. As you get bigger, it gets harder to do it. And one of the things that I, that I'm trying to do is, is run a big business. Like, it's a small one. And let's, let's talk about the people side here for a minute because we've been talking a lot about data and analytics and stuff like that, but as you've been across a number of large businesses, I mean you must have dealt with all kinds of issues people wise and just in general, just like seeing so much. I mean we have about 200 employees, I don't know how many employees at Posh Peanut.
Jenna Habayeb
60 at Posh, which is interesting because I've had hundred person marketing teams before, so it's like such an interesting shift.
Jason
That's, that's incredible. So like, and, and it's, I feel like the people side, you just, with so much information out there now, everything going viral, people being able to just like spread the word about anything inside an organization. How, what, how are you dealing with like the people side of your organization today?
Jenna Habayeb
Did you have something really bad happen to you? Because I feel like you're like, so we have a PR crisis. Can you help me solve it? A friend of mine.
Jason
No. You know what it is like for, for me on, I'm, I'm a little bit older, so I'm a little bit old school and I'd have, I've had to adapt to, you know, just, just you know, new generations of people. And I think there are, there are, but there are like, there are different ways of doing it. You know, some people, like, oh, you just have to manage people the way they need to be managed. And other people are like, no, you just gotta just manage people the way you want to get things done. Like, I would love to hear, like, two perspectives from two, like, incredible killer women. Like, their. Their view on just, you know, people management and the people side of. Of your job. Let's start with Shereen.
Jenna Habayeb
Yeah.
Sherene Aubert
I think about this all the time because it's like. It's like there's two beasts inside of me. The one that wants what it wants, and then the one that's like, maybe I should chill a little bit, you
Jenna Habayeb
know,
Sherene Aubert
be, like, a little bit more human in this moment. But it's hard because when you're driving a team up a mountain, it's not easy. Like, climbing a mountain is not easy. And you want them to not get distracted. You want them to stay focused, and you have to keep instilling what you believe. Like, the direction is. Because people have a tendency to, like, wander, look. Look at other objects. It's like, no, we're going up the mountain. Remember, we're going up the mountain. And it's. It's. Sometimes for me, it gets hard to be like, okay, everyone has different things going on. They have different styles of working. They have different styles of learning. Like, and there are moments that you have to adapt to that person, and there are moments that you have to be like, okay, we're just. We're getting back in the boat and we're rowing. And I think what. What helps is finding ways to communicate that to people. Like, if we. We can debate. Like, I. Sometimes I'm open to debate, and I will ask for opinions, and other times, I just want us to get in the boat and row. And sometimes I've even had to tell people, hey, when. When I say, like, this is the direction we're going in, that means, like, the debate's over. Like, this is the direction we're going in. But I think it helps for people to even know, like, have that verbal cue so that when you have a conversation with them, you can be like, all right, this is the direction. And then they just know. Like, that's the cue that, like, okay, the debate's over. We're going.
Jenna Habayeb
We're getting in the boat, and we're rowing.
Sherene Aubert
But I think I've watched Jenna handle, like, manage a team, a large team. And it's so impressive, Jenna, because you're like, no, you're no bs. You're Very direct, but you're very gracious. Like, you're. You're super kind, but you will, like, you also do this. You have these, like, verbal cues where you'll say, elmo. What is Elmo again?
Jenna Habayeb
Elmo. Enough. Let's move on. I had to bring that to a meeting. I'm like, guys, like, on the next thing, like, we gotta go.
Sherene Aubert
Yeah. And it's. It's like those little. Like, they're like, everyone has them. Everyone has these, like, little phrases that tell the team. Like, okay, it's like, let's just go. Let's just move on. So I don't know. But I. Yeah. Jenna, what about you?
Jenna Habayeb
No, I mean, I. I really. I enjoy working with Shreen because I think we have very similar working styles. I mean, look, I also think it's hard. All three of us grew up in a day and age where you went to work and you worked hard and you waited till your boss left, Right? Like, maybe. I don't know. That was my experience. I was like, I'm not leaving before my boss leaves. And then, obviously, the rise of COVID new generations coming into the workforce, it's kind of, like, hard to break that mental model of, like, you got to put the sweat equity in. Like, you don't. You don't just become a CMO overnight. Like, you bust your butt to get there. And so I think there's a little bit of, how do you lead with positivity and motivation. But again, I think, yeah, to Sherene's point, you know, being very specific and direct, I. You know, one of the things I initiated with the team this year, as we shared out our budget, as we shared out our vision for the year, is kind of like a Hallmark phrase for our team, which is simplify to amplify. And I'm forcing the team to ruthlessly focus. If it is not on this agenda, you need to be proving to me why we need to be focusing on this. Like, if it is not. If it's because we're wildly missing numbers and we need to find a new avenue, great. But I think a lot of that, even my. The Elmo phrase, I really. It's, like, about reigning the team in because I. I think there's way too many shiny objects or squirrel that people are focused on, and it's like, it's all about, what is it we need to solve? What are the actions we're taking? How do we get them? Let's move. And then, you know, it's just, like, keeping the momentum going and that's what I try and do. But I do, I always try and do it with positivity because I find at least people are more motivated and excited when their leader is motivated and excited and hungry than if they're upset and you know, driving you to feel like, well, I don't have any good ideas.
Jason
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Jason
You guys should, you should totally like write a book on leadership. Seriously. Because I think it's so lacking today. I love what Shereen said about, you know, how you have to drive people up the mountain but you have to be human in the moment sometimes too and there's that tension. And you, you both make me feel a lot better about the way I do things because I sometimes worry if I'm being too tough with people. You know I grew up in big law, investment banking. Grew a bunch of tech companies like and I, I, when I was a, when I was a first year associate at Scadden as an M and a lawyer, there was this one of counsel who I used to work for and every time he would, I would be leaving his office he would say just get it done Jason, just get it done. He would like be mumbling, muttering it under his breath. It was, it was really weird. But like I think about this every day and I, I talk about our GSD DNA get done, right? And ultimately there's that balance between being human and getting it done. I feel like I have heard people in the organization are like, are intimidated by me and I don't like that. You know, I don't want, I don't like, oh, people are afraid to, they have a meeting with you, they have to present something. They're really afraid. I give people a hard time about their presentations because I think people don't know how to do presentations. But it's like, I give it out equally. You know, like, I give it out equally, and it's. But I think the message that you're both giving is like, you know, being human is not the same as, like, having to coddle everyone. I feel like everyone, you know, needs a therapy cat or something these days. And it's like, wait a minute. Like, do you really need to. Do we need to bring therapy dogs in once a week to pet, to make everyone feel good? Or, like, can you go home for that?
Sherene Aubert
It's so true. I feel like the more you spend time as a leader, the more you. It's like, do I want to be popular or do I want to drive the team to excellence? Because sometimes those two things are in opposition of each other. And I have to remind myself, like, you know, I can get frustrated as a leader sometimes, and I have to remind myself, like, you know, well, I'm actually here as a coach. I'm teaching someone something that they probably haven't learned before. I've had experiences that they haven't had before, so it's unfair for me to explain that they would see the world that. The way that I see them. I have context that they don't have. I might have been doing this longer than they have. And this is. This is like an opportunity for me to. To really help someone get to the next level of their career and teach them the things that I learned. And I can either do that in a way that, you know, they'll remember, like, wow, this person was such a kind teacher to me, or this person was an a hole. And I. Sometimes it's both, sometimes it's both.
Jenna Habayeb
But I've never seen Shereen as an a hole, by the way. Like, she's always. She probably has it in her own head, but you've always been really thoughtful, kind, and intentional, even if you're delivering hard.
Jason
You could tell from her tweets, though, that she's a killer. Like, I love being around killers. Like, the question is, you know, should you accept mediocrity or not? Because, you know, this is just like, we're. We're the kindler, gentler managers. And I really think that you just. If you just accept enough mediocrity, you're going to fail, right? If you. If you allow for drama, you know, if you allow for gossip and all in all that stuff at the. Like, you just. You just have to kill that stuff as. As quickly as possible. Um, and I. I just love hearing from both of you that I. I feel like we're on the same page, Jenna.
Jenna Habayeb
Yeah, I. I think. I think we are. I think the. The hardest thing as a leader, you know, in this type of a leadership style, is it actually takes more work to not just blurt out how you're emotionally feeling in that moment and being able to take. I'm talking a nanosecond pause in your own brain to package it up, right? Like, again, I. I'm. This. Everybody's different. I'm the kind of person that's like, instead of being like, this is. I can't believe you did this. Like, I'm putting somebody in the corner, is going to go cry and be like, I don't even know how to, like, do. How am I supposed to use that? It's not productive feedback versus. Hey, I'm. I'm pretty disappointed with this. Have you thought about this, this and this? Can you go back, right? You can get a better result out of that. It just takes more time and effort for me to have to distill that in my own brain, package it and, you know, present it.
Jason
This is what everyone has to do at work. Like, and this is what I've been telling people forever. It's like, facts don't care about your feelings. And like, there's. There are two types of decision making in your brain. Like, Kahneman and Tversky have written about this. If you don't know who they are, they are like behavioral economics and really about cognitive biases and how people make decisions. I'm really big on this. System A is like your fight or flight decision making, emotional decision making. That's like the stuff that you needed to save your life, right? And then system B is your thoughtful, logical way of making decisions. And as human beings, we're always in a, like, a fight between system A and system B. It's just like, by its nature, it's like programmed into. It's like our. You know, people talk about your lizard brain, right? And it's like you have to constantly drive yourself and everyone else in the organization to be system B. You know, there's gotta be some system A, especially in marketing and creative and all that. Like, how does. How does this resonate? But, like, there's way too much system A out there, guys. Like, we gotta get people in system B. And I think you. I think you, like, naturally get that.
Sherene Aubert
Anyone who wants to become a good leader, just have some kids. Because, like, if you think your team is testing you, just have some kids and then you'll really learn what it means to be tested.
Jenna Habayeb
But I think, Shereen, I honestly think motherhood helps because it's like, you can't just be like. To my point, you're. Why'd you do that? It's like, like, all right, hon, we need to get the shoes on so that we don't step on the thing. Like, you know, it's like, we got. Gotta get going.
Sherene Aubert
So many parallels.
Jason
This has been awesome. I'm really, I'm so grateful that to have an hour to talk with both of you today, it's really. It's really inspiring to see what you've both done in your careers and created and how you. What kind of leadership you. You bring to. To your organizations and the ability to go from being a brand creative person to a performance marketer to managing, like, the entire thing. And, I mean, I've known Shereen for a while. Like I said, I tried to hire her. She's just like a killer. I love.
Jenna Habayeb
I did too.
Jason
I love. I love being around killers. I've learned a lot from you both today, so thanks for coming on. My daughter Zoe is 22, and she's graduating from Wake Forest doing communications and marketing. I would love for her to, like, chat with each of you for 15 minutes at some point. I'm telling you, she's an absolute killer, and you're going to love her. And I just, I think she needs to know both of you.
Sherene Aubert
I would love that.
Jenna Habayeb
I would love it.
Date: April 8, 2026
Host: Jason (with co-host Sherene Aubert)
Guest: Jenna Habayeb, President of Posh Peanut
This episode centers on the meteoric growth journey of Jenna Habayeb, from agency marketer to full-stack CMO and now President at Posh Peanut, the beloved children’s apparel brand. The conversation dives deep into the art and science of scaling eCommerce businesses, data infrastructure, the community flywheel, and the evolving nature of leadership. Jenna and Sherene, both seasoned operators, provide powerful insights about building cult brands, leveraging data and AI, and leading high-performing teams while staying human.
Background:
Jenna traces her path from large creative agencies like Ogilvy, to brand-building at Splendid and 7 For All Mankind, entering the wild west of cannabis, then leading brand/growth at Ipsy (growing from $300M to $1B), onto CMO+ (CRO) duties at Ruggable, and now President at Posh Peanut.
"I spent five years at ipsy ... grew the business from 300 million to a billion. ... I'm now in my first president role at Posh Peanut. So, yeah, it's been an interesting arc—not something I necessarily expected, but a wild ride so far."
— Jenna Habayeb [02:53]
Topic: The “Forgotten Community Flywheel”—leveraging community for growth.
"It's sometimes untapped because we get into this world of growth marketing ... live in spreadsheets, building out forecasts ... and forget to take a step back and say, well, what is actually driving my business? ... Great brands are highly engaging with their community."
— Jenna Habayeb [05:14]
"[Posh Peanut has] 250,000 people [in its Facebook community] ... the reality of being able to engage and have your customers react in real time, it's pretty unbelievable."
— Jenna Habayeb [09:02]
Topic: How Jenna’s agency background set her up for success as a brand operator.
"You have to be on top of every single trend ... you deeply immerse yourself in all the new things and really understand the customer."
— Jenna Habayeb [14:06]
Topic: Posh Peanut’s deep investment in data, the transformation toward being a data-first, AI-augmented operation.
"When I first came in ... we did not have a good handle on our inventory ... and [Saris] helped us, in three months, get into a phenomenal place ... Inventory is capital. That is dollars sitting there that can drive my business."
— Jenna Habayeb [29:28]
"I really want to find a way to simplify this and how can AI help ... I don't want to go to Shopify or look into six dashboards ... I want to get those quickly so we can react quickly."
— Jenna Habayeb [36:40]
Topic: Jenna’s leap from CMO/Growth to business owner.
"With Ruggable ... if none of [the new rugs] sold, none of them were made. ... With Posh, if we buy 100 hot pink onesies and don't sell them? Guess what—I have to deal with that. So that was a big mental shift."
— Jenna Habayeb [45:21]
Case Study: Seven For All Mankind
How?
"Operational efficiency ... intentionally consolidating [teams] where we thought we could get the best operational efficiency ... and then keeping subject matter expertise, especially in the places of brand distinction and in design ... that helped us drive a more efficient business."
— Jenna Habayeb [50:50]
Topic: Modern people management, motivating for high performance without losing empathy.
[53:53–63:13]
"People are more motivated and excited when their leader is motivated and excited and hungry than if they're upset ... It's about reining the team in; it's all about what is it we need to solve? What are the actions we're taking? Let's move."
— Jenna Habayeb [57:12, 59:11]
This episode is an inside look at scaling, sustaining culture, and operational excellence at a brand poised at the intersection of community, data, and relentless execution. Jenna and Sherene embody the “sheep from the goats” mentality—operators who “stretch” themselves across creative, growth, analytics, and people leadership. Listeners are reminded that, all the technology and trendspotting aside, the common denominator of enduring brands is a leadership style that combines rigor, focus, transparency, and—above all—authenticity.
For aspiring brand leaders and operators, this episode is a masterclass in growth mindset, operational discipline, and people leadership—delivered with honesty and a bit of irreverence.
Note: Ads, sponsor content, and non-core banter have been omitted for clarity and directness.