---
title: "From Fortune 1 to 100 Person Startup: A CRO's Bet on Creative"
episode: 84
podcast: "The LeanScale Podcast"
publisher: "LeanScale"
guest: "Gabby Stoller"
guest_title: "Chief Revenue Officer, Big Happy"
date_published: 2026-05-29
date_modified: 2026-07-22
duration: 00:51:06
word_count: 8729
topics: ["gtm-strategy", "sales-leadership", "brand-positioning", "demand-generation", "ai-in-gtm"]
canonical_url: https://leanscale-knowledge-hub.netlify.app/podcast/gabby-stoller-cro-bet-on-creative/
source: "LeanScale Podcast Knowledge Hub — https://leanscale-knowledge-hub.netlify.app"
license: "Free to quote and cite with attribution to The LeanScale Podcast."
---

# From Fortune 1 to 100 Person Startup: A CRO's Bet on Creative — Full Transcript

> Episode 84 of The LeanScale Podcast, with Gabby Stoller.
> Published May 29, 2026 · 00:51:06 · 8,729 words.
> Machine-transcribed and **not diarized** — speaker attribution is inferred, so verify
> attribution against the audio before quoting a specific person.
> Structured breakdown: https://leanscale-knowledge-hub.netlify.app/podcast/gabby-stoller-cro-bet-on-creative/

## 00:00 — Gabby's journey: from Walmart to Big Happy

**[0:00]** (logo whooshing) Today, I'm talking with Gabby Stoller, the Chief Revenue Officer at Big Happy, a creative first ad tech platform that's been called the Pixar of digital advertising. What makes Gabby's story interesting is where she came from. She spent nearly five years at Walmart Connect, running some of the most complex CPG verticals in retail media. And before that, she built her career across the entire ad stack. Yahoo, The New York Times, Verve, Placed, Vistar Media. She's been at publisher, platform, retail media, and now ad tech. Last June, she left the number one fortune company to join a sub 100 person startup. Within six months, she went from GM

**[0:50]** of their digital out of home division to Chief Revenue Officer. We're going to dig into why she made that leap, how Big Happy is winning with creative first strategy, and what she sees happening at the intersection of digital out of home, retail media, and 3D advertising. Gabby, you left Walmart Connect Fortune One, one of the biggest retail media networks for a company with less than 100 people. Walk me through what pulled you away. - Yes, I'll start with that Walmart Connect was the most incredible experience, and I am so grateful for being there for five years and helping to lead divisions under the food end today.

**[1:31]** It was amazing, and I genuinely feel like I got my MBA, and I got paid to work there at the same time. And what drew me to Big Happy? Because most people would be like, "Why did you leave Fortune One to go here?" From a Big Happy standpoint, several of my old colleagues work here. The CEO of Founder was a former coworker of mine, and he's just one of the most brilliant people I've ever met in my life. But outside of that, the excitement around this creative first mentality is something that I've missed. We spend so much time, and I spend so much time at Walmart speaking about the precision of audiences

**[2:08]** and reaching consumers using such hyper-focused tactics. And sometimes the creative was a mess. And not to say that's necessarily on the Walmart side, but just in general, creative tends to be a bit of an afterthought after spending so much time on audience design. So what I'm loving about this side and being able to come over here and to build something is really that creative first mentality and making sure that we're speaking to audiences at scale with the right message. But being able to do it in this really organic way that's gonna resonate and drive tremendous results. I think what excited me the most about the Big Happy opportunity

**[2:48]** was building a division from the ground up. So while I was at Walmart, I was involved in their digital out-of-home work stream. And I loved that we were lighting up the store and being really intentional with screens in the store. After all, it's a really protected asset. You don't wanna invade the consumer journey. You don't wanna necessarily get in the way of their path to purchase or their path to shelf. But what I loved about Big Happy is that they were starting to build out this digital out-of-home division, taking what they've done on mobile and bringing it to a new screen that's a bigger canvas that allows the creative to really be

**[3:23]** the epicenter of everything. And being to get to do that from the ground up was just incredibly exciting. I love to build. I love to see things from start to finish. I've done my fingerprints on it, be a part of like the planning, the strategizing, the failing, the winning, and essentially commercializing the go-to-market strategy. That to me was really, really exciting. I felt like I did that at Walmart with the food team. I was one of the first 20 employees that was on the food team. By the time I left, it was over 400. So I felt like I got to do that there. And getting to do it at a company over here as well was just incredible.

**[4:01]** And the leadership here also gravitated me, considering that we've worked together previously as well. - Yeah, it always helps when you can follow people that you have that level of trust built with. It just makes the working relationship so much easier. - I'm fortunate enough at Lean Scale, COO is my childhood best friend, best man in my wedding, godfather of my three children. And I think when you are in an environment where you can work with people like that, it just makes it so much more enjoyable. - It's so special, yeah. We build a lot of connections over our course of time. And I think there's six of us over here

**[4:37]** that were formerly at Verve together. So we're a little mini family getting to do great things, but all had different experiences that brought us here. So we're bringing all that background and leadership and skill sets that we picked up along the way. - Absolutely. - It's nice to see each other evolve. - I'm definitely gonna wanna get into your approach to go to market strategy, how you even started as you were building out this new division from scratch. But before we do that, I would really like to dive in a little bit more on the creative first strategy. Because I think, especially me sitting in the go to market ops revenue operations world,

## 05:04 — Creative-first strategy: the heart of Big Happy

**[5:18]** sometimes people become too obsessed with just the numbers and just doing things where you can get an exact conversion tracking where it's all typically coming from creative anyway. But I'm curious the strategy and also how you convey that to clients in a way that they'll understand. - Absolutely. So I mean, on our side at Big Happy, what's really nice is that we're putting ourselves in the shoes of the consumer. We know if you take your advertising hat out of it, I'm walking down the street, I'm looking at my mobile device, I'm looking at ads in general, but the ones that are most memorable are the ones that are big and bold, have great colors.

**[6:03]** It's not the same TV spot that I already had my eye on that's sitting at home. It's ones that speak to me based on the environment that I'm in. And then you take into account how hyper targeted we can be now, that's beautiful, data is a gift. And I think that agencies and brand marketers, they have access to first party data, third party data, and they're spending so much time on these audience cohorts that they really know are gonna drive that sale or drive that awareness or who they have to reach with whatever desired outcome the goal has for the campaign. But if you're using the same creative to speak to all those different audiences, what's the purpose?

**[6:44]** There's so much wasted media dollars that are getting out there after you spend so much time talking about who you are trying to reach and having to try to do something either offline or online. If you're not customizing the creative or thinking about the mindset they're in for the creative and having it speak to them in a certain way, brands can miss the mark. And essentially then they're not necessarily driving the ROI that they're expected to. And so if you start with what am I trying to say and what am I trying to achieve? If it's upper funnel, you wanna have your creative look one way. If it's that you're trying to reach moms in pediatrician offices,

**[7:23]** speak to them in a different way. If you wanna reach them while they're on the go on their mobile device, speak to them in a very different way as well that's more like KPI driven. But this is art of storytelling. You're gonna reach her, him or they, or whoever it is that you're trying to reach pet owners along their journey. But if you are speaking to them with one creative message, what's the point? So we really here take that creative first mindset that every ad is a blank canvas. Our tech stack allows us to do this at scale. It allows us to be turned key, but it allows us to be really intentional with the message that we're deploying

**[8:03]** against each audience cohort, against each of the mindsets that they may be in. And the results show that. Brands want to speak to consumers. They want to resonate with them. They want to make an impact and be like long lasting. But again, if you're sending the same message that you already serve them on TV and you're oversaturating them with a message that's not customized to where they are in their consumer journey or their path to purchase, or if it's sitting in their cart and they haven't checked out yet, you could be that much more intentional. And it doesn't cost that much more to do that, but it allows you to have the results on the backend

**[8:42]** from the conversion standpoint that all of us are being held to from an ad tech perspective. - I think we're seeing this not just in advertising, but we're seeing in cold outreach as well. Now that people have access to these tools that can produce almost unlimited content and unlimited assets, it starts to become an issue where the amount of noise has significantly increased. It's 100x more information and everybody's fighting for intention. So now it becomes who can get it personalized the best, who can find those right intent signals where you're meeting them the moment they're ready to hear your message and where the pain is really resonating.

**[9:27]** And I think if you're not, volume almost, it's almost irrelevant. It's like, we have to figure out how personalized and tailored can we make this thing for this person? - Yeah, and for out of home in particular, it's really interesting because the way that out of home and structured, you almost change the content to the mindset and the location of where the screen is. So on our side, we have access to a million plus screens, everything that we do is 3D enabled, so we need video to be like the filter that's on our inventory. But we're thinking about dwell time, we're thinking about mindset, we're thinking about the contextual relevancy

**[10:11]** based on who the desired consumer is. So I spoke about a mom earlier, I know that's always the example everyone goes to, but let's just go to pet owners, I'll start with that. If you're thinking about a pet owner, there's a couple of different ways that you could be really creative strategically with the venues you're gonna select. So it could be apartment buildings that allow pets, it could be hotel screens that allow families to bring their pets along with them on their trips. It can be in veterinarian offices. And those are just three very different examples of how you could be so creative with the strategy, but then what we would wanna do

**[10:48]** is make sure that each creative message in each of those different environments is a little bit different. So that speaking to them in this one-to-many environment, it's not giving them that creep factor, it's more contextualized 'cause it's one-to-many, but it does allow the brand to seem very responsible for how they're talking to each of the different consumers based on where they are at that moment in time. And again, it's targeted, but it's not hyper-targeted in a way where it allows it to resonate with many and again, to cause a desired outcome that a brand may have. - Yeah, I definitely think there's a spectrum of,

**[11:26]** this is intentional and this is invasive and creepy.

**[11:33]** And balancing that I think is quite an art to where, hey, you're also doing it in an organic way where you're not like, oh, I saw that you checked into this hotel and now here's an ad for this thing. It's like, okay, I feel a little targeted, as you mentioned, but I think balancing that is really, really important for a brand. - Yeah, and there's so many signals available for us to be really strategic with targeting. So of course on mobile, that's been around for quite some time where you can get really hyper-targeted, which is how we built our business, but for digital out of home, there's ways to find out what screens over-index for an audience

**[12:17]** and use that to get even that much more prescriptive. And so you're using signals because you know it over-indexes. It likely will have a purpose, even more so to achieve your goals. Now, how do we get the creative to match that targeting? And it can be as simple as a copy change. It could be as simple as a color change. It could be as simple as having it run when it's really nice out so that from a pet owner perspective, it's when they're taking their dogs for a walk, for example. So you're just using all of these signals, but the creative can speak to it. So something like sunshine on an ad or rain clouds on an ad based on those signals,

**[13:01]** it's really organic, it's authentic, but it makes it relevant. And more importantly, it makes it memorable. It makes that lasting impression, which all brands are competing for at this moment in time, is how do I make a lasting impression? There's so much noise. Intention spans, to your point earlier, are more limited. And so, great creative is what makes you stand out and minimizes all the fragmentation on that noise. - 100%. Walk me through leaving Walmart Connect, coming over to Big Happy, to build out the digital out-of-home, and maybe before going into the strategy, for those listening who might not know what that is

**[13:41]** or they're not as familiar with the ad tech space, what digital out-of-home is and what falls in that bucket, and then what did you do to build it? How did you approach that? - Amazing, I love this question. So, digital out-of-home are all the screens outside in the physical world that are either outdoor, so if you think about things like billboards or urban panels or bus shelters, then there's place-based inventory, so things like you'll see screens at gyms that serve ads or movie theaters or malls or grocery stores, and then it gets all the way down to even the point of purchase where it's in aisle at a grocery store or a liquor store,

## 14:14 — Understanding digital out-of-home advertising

**[14:21]** so there's a wide vast amount of screens that are available that rotate, that accept digital ads, and it's much more of that mindset-based targeting, but thinking about consumers in that one-to-many medium in the outdoor space, you could buy it either direct or there's a lot of screens that are available programmatically, which means it's more automated and it's connected to SSPs and DSPs, so on the Big Happy side of the house, when I came over, we first had to assess all the available partners for us to go to market. We don't own and operate any of the inventories, so we really had to make sure that we were setting ourselves up for success,

**[15:01]** really from an omni lens, because we've been around for six years on the mobile side, we really believe in the power of storytelling across both channels, so we really evaluated where can we do both mobile and digital out of home, where are there retargeting capabilities so that we could continue that art of exposure with the storytelling to continue on mobile after out of home exposure, and what are the pipes that are necessary for us to do this in a scalable fashion, and so we really went through a major assessment process. I come from the out of home space, not just from my time at Walmart, where I helped with that and gave a lot of feedback

**[15:40]** for how they productized the in-store, but I also worked previously at a massive digital out of home organization, Vistar Media, who are absolutely incredible, and so I got a lot of the fundamentals on what was really important in this space in order to commercialize, so we started out doing managed service and just bringing in a select few partners that we could really take their mobile business, and they grew and they trust us to expanding to digital out of home as our betas, and really made sure that everything was firing, so our creative was firing. We were compressing it and rendering it to the spec for each of the different media owners,

**[16:21]** and by doing it as managed service that allowed us to fail and then win, fail and then win, and eventually, after going through a couple different rounds and making sure all the pipes were correct, just winning, and after that, we were able to expand to more of the self-service capacity, which allowed brands to more transact themselves, being hands-on keys or their agencies, which was a massive unlock, and then we really just made sure that all of our brands had this appetite for the two pads that we really wanted to move forward with, which was we could be hands-on keys as managed, or you can do self,

**[16:58]** and then the last but not least component of it, of course, is measurement and accountability, so for the last six years, we've had a lot of measurement partners in the mix for mobile who also measures out of home, who has a really sound methodology, and how could they help us understand the impact of the two channels together and really prove out that the power of 3D creative and digital out of home is gonna resonate that much more in market via a brand study or a foot traffic study or a sales of study, so we kind of put together this end-to-end platform where creative was the first approach. We made sure we had the distribution

**[17:37]** and a bunch of the different supply sources that can accept what we're doing, made sure that mobile was an extension capability so that we could do the art of storytelling and continue that omni approach, and then how do you close the loop from a measurement perspective to prove out the KPIs? We built it so fast, and so one of the things that I've loved about being here and being back at this 100-person organization is just we are able to react and pivot and to make decisions so quickly that we basically slated three months for go-to-market, and we were live within less than 60 days, and then once we were live within 60 days from a managed perspective,

**[18:22]** we were able to then break into self-serve within 90 to 120, which exceeded all of the benchmarks we set for ourself, and so I quickly realized that there was such an appetite for really great creative on such a beautiful canvas that we just needed to tell the story about why 3D, why 3D always sometimes gets associated with being complicated, but we take away all those headaches, and why can you do it at scale and not be concerned it's not gonna work accordingly. It doesn't always just have to live on the big splashy Times Square as a one-off. It could also be complimented programmatically across the board on any screen that accepts video,

**[19:09]** and so we got a lot of folks across the industry that are really creative thought leaders. We got a lot of intel and competitive intelligence from the sense of like, what are they looking for? What are some roadblocks when you think about 3D? What are some of the headaches that you associate to it? It's typically, it's expensive, it's long turnaround times, and we just wanted to make sure that everyone got really comfortable that we take that out of the equation, and once we were able to do all that and build our narrative and prove that it works, we've really been a market, and it is definitely taking off faster than we ever could have anticipated,

**[19:45]** which has been really rewarding because seeing something from the ground up is probably the biggest compliment to the strategy, and the best group of rock stars that I work with over here that were able to help us like from a cross-functional perspective. - There's nothing better than when you start to feel that momentum and the flywheel turning faster than maybe you can even keep up with. One of the companies that we work with, they're a wealth management tech platform, and they made a huge pivot. They went from direct to consumer to selling what their solution was to advisors, and the second they made that strategy change, immediately you saw the sales

## 20:26 — Building momentum: key strategies for success

**[20:32]** just increasing at a rapid rate. I'm wondering, in your experience with Big Happy, what were some of the things that just started being aha moments where things started clicking? Was there a certain sales motion you were running? Was it a channel partner? Was it when you launched Self-serve? What was that shift where it felt like everything changed and the momentum started stacking? - I would say the education internally with Big Happy was really important. We were really intentional with who was representing the Out of Home channel to make sure that it was folks that were experienced in this space, and then we were responsible for the education

**[21:13]** within an organization that was predominantly mobile. So I think internally we made sure we did a lot of series, we did a lot of certifications, we went through the rigor mall to make sure that everyone was really up to speed on what is digital out of home, why digital out of home for Big Happy, and we showed the roadmap and the progression of how we planned to get everyone on board. For all of 2025, it was essentially just a couple of us that were representing solely digital out of home that really went out and represented and brought all that feedback back internally to ensure that our storyline and our narrative was resonating.

**[21:54]** But more importantly, that we took the feedback from our clients and our agencies and trusted resources in the industry to really bring to the forefront the strategy that they needed to deploy and to make it easily digestible. Once we did all of that, we became an omni-platform as of January 1st. That is when everyone available with Big Happy had access to both channels to sell, and more importantly, our brands and our agencies got access to it as well, because we used all 25 to be our testing ground, make sure everything was up and running, and proper, we had case studies, we had results, we saw everything was rendering,

**[22:32]** and we had all of our resources also officially trained so that everyone spanned across both digital out of home and mobile. From a tech stack perspective, it's one and the same. We are CGI-infused, so everything that we do sits on this proprietary tech stack that allows us to do rendering and compressing at scale and to do it really turnkey. That's our secret sauce, that's our bread and butter. So once we saw how simple it was for Big Happy, it's not simple in the marketplace, but simple for Big Happy, to be able to go from mobile digital out of home at scale, and we got all of our timelines to a really good place that we felt comfortable with

**[23:10]** that are much shorter than the industry standard, we then brought it to the market for a jam-on launch for everyone, and that's when we're starting to see a lot of brands come forward with interest. We wanna be agnostic for how they deploy. So if they want our team to be hands-on keys, we are happy to. Of course, we have the tools, we have the resources, but a lot wanna run in OmniDSPs where all their other media is running, so they can manage frequency, they can manage the retargeting, they can manage all of their media in one seat, and so we had to make sure that that was an option. So I would say that definitely accelerated the growth

**[23:50]** because we were super easy to transact with 'cause we are really agnostic, but I would say it's more the education piece and making sure that everyone was representing Big Happy and understood the evolving channel that we were getting into at out of home. - What were some of the most successful go-to-market motions you were running? Are you capturing your clients through a sales-led motion or working through channels? How are you getting new clients? - I would say we've really stepped up our marketing, which has been really exciting. So we are definitely attending a lot more conferences that make a lot of sense for the verticals

**[24:30]** that we see the highest client volume in, but also ones that we know, once they are educated on our offering, will gravitate to what we're doing. So for example, we are very aligned with a company known as Media Post. For those that you aren't familiar, they're a publisher, but they also have a ton of events and they're verticalized. So on our side, we've made sure to go to the farmer one, for example, because farmer for us is a massive category on the mobile side. We have custom ISI scroller creative that is widely adopted and it's really built to our tech stack and it's accepted over 7,000 mobile publisher sites.

**[25:08]** So it's scalable, it's custom, it's beautiful. It allows brands in the pharma space to really be memorable and to stand out, but not too much. It's still like advised by all of the regulations they have to go through, of course, and that red tape. Digital out of home for pharma is a massive opportunity. It's one to many. It's not as invasive. It doesn't feel as personalized. It still could have custom creative that is memorable. And you're able to target doctor offices. You're able to geofence different conferences to reach HCP professionals. But we wanted to make sure that we were concentrated on events where we could speak directly

**[25:49]** to those in the pharma industry and to do that. So we attended the media post pharma. That was incredible for us. We're doing the same on CPG and retail and showing up at the other events like CAN, CES, and possible and those industry thought leader ones just to ensure that we are able to tell our story. So outside of events and marketing, which has been really successful for us, we've also had a lot of penetration with the agencies. And we've had that over time. So the team has done a great job really making sure that the account teams at agencies understand Big Happy both from a mobile perspective and now from a digital out of home perspective.

**[26:28]** But we work with some of the top brands in the country. And if they were using us for one channel, been working with us for years and years, and now we've triangulated that partnership to a client we've built that trust. So now we've got the agency who understands the power of Big Happy. We have the clients that love creative just in general 'cause it's how they tell their brand story. And then you have us in the room and it's all three of us collectively. We're building something pretty magical because we're taking a brand's positioning. The agency is able to help deploy and be the strategy arm behind it. And we're helping build a creative that matters

**[27:03]** that's gonna land and resonate. We take all those learnings, compile it with measurement. It's powerful. And so I would say we've been really strategic with our go-to market where we're making sure it is events focused, hyper-focused on the right places to be in the environments and the industries we wanna win in. Plus making sure that we're speaking to nationally all the agencies, as many of the brands that we can that already work with us and to drive a lot of that education and testing. We do a lot of mocks also. So on our side, because our tech is so fast, we have the ability to really bring something to each meeting that's a bit customized.

## 27:41 — Strategic go-to-market approaches

**[27:45]** So brands love to see their brand on a mobile device. How does that look? Or on an out of home screen in three day. And so when they see it live, there's this aha moment of, wow, I actually really can do this. And they only got this meeting a week and a half ago and they're showing up at this mock already, they're preaching what they're saying that they could do, which is speed, great creative, personalization and white glove service in the sense of the way that we treat our customers is top notch. We are known for that in the industry and we just continue to prove that time and time again. - One of the areas you mentioned

**[28:21]** when you're partnering with the agencies, we had Mike Head, he's the CRO of Partner Stack, one of the biggest partner management platforms as well as partner ecosystems on the market. And there are so many stats of the increase of LTV of a customer if you have a partner involved because then you have two companies invested in the customer success that are also holding each other accountable because they have more at stake than just that customer. So I think any go to market motion that can involve some level of partnership to have a better together story for the customer is always a huge win. - Yeah, and I don't know if you saw the recent press,

**[29:03]** I think you probably have 'cause I think we spoke about it, but we announced our board of advisors. And so that is something too that we're really excited about. It just came out a week or so ago, but we announced a lot of industry thought leaders across ad tech, across smart tech, across B2B, across Brand Direct and agencies that were bringing everyone together to be a sounding board for us because we're only continuing to grow. We are climbing up a mountain and it is happening really fast. I think we've accelerated so quickly and it's a beautiful thing, but we also have to keep a pulse and making sure that as we're continuing to scale,

**[29:46]** we're hitting the mark and delivering and being accountable. And having a board of advisors for Big Happy has always been something that we've desired for. And now we're actually at a point where we've scaled so much that we're drawing the attention of a lot of thought leaders that we are just so excited to get to be a part of this fun journey and take us to the next level. - One of the things I find really interesting, you came to Big Happy to create the Digital Out of Home division, came in as a GM, and then moved into the Chief Revenue Officer role. What, in your mind, was the biggest difference between being a GM of that product line

**[30:26]** and then sitting in the CRO seat above the entire go-to-market engine? - It's amazing. I'm honored and I'm touched that they saw the impact that I was able to make from a Digital Out of Home division perspective and how quickly we were able to scale that. Again, we exceeded all expectations. All of us thought this could be a standalone division for quite some time, but because of the market receptivity to the two channels together and this gap of great creative across multiple channels and being able to do this art of storytelling in 3D and making it pop, it took off so fast. And so we couldn't necessarily just have a couple

## 30:45 — The role of partnerships in success

**[31:07]** of us representing it when the demand was so strong that wouldn't be fair to the advertisers that had been working with us on mobile for so long. So it made sense to make sure that everyone was able to successfully represent both channels due to the demand driving that. So stepping into this role was really exciting because it's a testament to how quickly we were able to scale a division and how much the market needed it because otherwise we wouldn't have had that much demand. And so we really feel like we were answering a lot of questions and it was a gift to the advertising community to be able to launch this 3D Digital Out of Home division

## 31:12 — Transitioning from GM to CRO

**[31:46]** with mobile as a sequential storytelling mechanism. Stepping into this role as of January was really interesting because now the Revorg consists of marketing and sales, which are also two separate divisions before I stepped over here. And so having both connected allows us to react quickly to market feedback. It allows us to ensure that we are putting out go-to-market materials that are necessary based on the questions that we're getting. It's this continuous feedback loop between what is the market asking for? How quickly can we put out materials that speak to that? Yeah, I mentioned the verticalized approach, but we're structured in a way

**[32:31]** by Holdco and agencies and indies. We also wanna make sure that we have some sneeze in-house that are able to speak to some of the verticals. And having things like that where we're concentrating at the Holdco, have some specialty areas that we see that we're getting a lot of excitement from. Sitting in the same org as marketing, it allows us to pump out materials that resonate so fast. And it's this flywheel that is continuous, but it allows us to almost work hand in hand in this really collaborative fashion that is speaking to the market and addressing all of their needs pretty quickly in turn K. Stepping into the CROC,

**[33:14]** what's been the biggest surprise to you? I always feel like, I mean, I've been in sales management for quite some time. While it wasn't necessarily over an entire sales org, it was always over like certain departments or divisions or certain regions. And I would say one of the things that I've enjoyed the most is learning how each market operates and just like some of the complexities and nuances and that's been really exciting. I wouldn't say it's a challenge. I just think it's something that I wasn't necessarily always exposed to being based on the East. So I've loved learning more about like the indie shops

**[33:59]** and how they plan to transact and like what makes them tick and the need that they have for partners like a Big Happy. And they may not necessarily be privy to like the New York Holdco structure, but there are a lot of overlapping ways that everyone behaves, but their needs may be a little bit different where they need this white glove service. They need a partner like we are over here doing and we treat everyone equally the same, no matter the size, et cetera. We genuinely just wanna bring great creative to the market. So I've enjoyed learning a little bit more about each of the different regions and getting more in deep with like that indie world,

## 34:03 — Understanding market dynamics

**[34:38]** just to understand how some companies are reacting and some of the things that they need and some of the gaps that we can fill for them. Yeah, I've always, typically I'm working with CROs and I think stepping into that and then seeing a bird's eye view of multiple things and figuring out how to get all those connected, especially on the product side, but you had the unique experience of really leading what that product strategy is as well and that offering strategy, not just the sales part, but hey, reeling together the entire go-to-market strategy. So I think you're probably teed up better than most people stepping into the official CRO role

**[35:21]** for the first time, just because of your experience. Yeah, it's fun. Listen, I love revenue. I love learning about revenue. I love identifying challenges and problems and helping everyone solve for them. The sales team here is just incredible, honestly. They love working here. There's such a passion for the product. There's a reason why we continue to win top great places to work and rising organizations and it's because of the love that everyone has for what we're doing over here. So stepping into the CRO role and getting to be a part of a bigger organization under the Big Happy umbrella, I get to work with the greatest humans

**[36:05]** who just love being here on a daily basis and I'm learning from them because they've been here for quite some time. And so they've also taken me under their wing to teach me how they've built the business from the ground up six years ago. And now we're able to put together both perspectives on adding digital at home to the mix. And when we're thinking about retail media, we're thinking about shopper marketing, which are a little bit newer frontiers for us, that makes so much sense. We're able to combine all of our knowledge and skill sets and build something together. And so there's a lot of like rolling up the sleeve, a lot of this go-to-market approach

**[36:44]** that I'm not doing single-handedly. I'm doing with the help of the team that's been here for quite some time, but just bringing my external POV and we're really able to scale it pretty quickly. And that's exciting to me. I thrive off of chaos, but I also thrive off of great energy. And that is something that is not limited here. Every single person here exudes this positive can-do attitude and that is contagious. And it only makes me wanna continue to represent them and continue to scale and help them solve any challenge that they may have. - That's so exciting. There's nothing better than having a worthy cause and then a very highly motivated team

**[37:24]** to work alongside of. - Definitely. - One thing that is keeping every CRO I talk to up at night is how to leverage AI in your own go-to-market motions. Now, I know Big Happy is using AI heavily extensively in your offering. How have you and your team adopted AI to go to market more effectively and more efficiently? - I would say we're just doing our due diligence before walking into a meeting. I think AI is a gift for anyone that is going to meet with a CMO, a brand manager, an agency. It allows you to really aggregate what's happening on the business level in a way that everyone's walking in incredibly prepared. And so while it's public information

## 38:09 — Leveraging AI in go-to-market strategies

**[38:16]** and earnings are out there and podcasts are out there, it's important to walk in knowing enough about the business so that you're coming in as an expert and you're able to gain that trust immediately, but also fact check. And if you see someone is down in unit sales and it's a CPG brand, maybe it's a distressed brand, maybe there are commodity issues, maybe there is something happened where that skew got eliminated at a really big retailer. And so coming in with all that knowledge just empowers you to have a really educational, collaborative discussion. And there's no excuse to not show up prepared because everything is at your fingertips.

**[39:00]** So on the tech side, of course, it's ingrained in a lot of what we do. And I would say we've been doing it for quite some time, even before AI was something that everyone was talking about. Like that's been ingrained in our tech stock for a while, but on like the sales and marketing front, it just allows us to be really prepared and to show up as educated as humanly possible and to ensure that every convo we leave with them understanding that we didn't come in, not thinking about their business strategically at the forefront. - Yeah, I think there are so many incredible tools available. I mean, here at Lean Scale, we're heavy power users of cloud code.

**[39:44]** We've built custom deep research agents, specifically to do what you're talking about, get prepared for a sales call, get prepared for a podcast, lots of ways that we're leveraging that. And also building it into our delivery workflows as well.

**[40:04]** Do you currently have a ops team at Big Happy? Do you have a, being in the CROC, I was always the secret weapon of the CROs that I was working with, but do you have RevOps, go-to-market ops? Do you have that function at your fingertips? - I do. So we have a business operations team where RevOps is part of, and then we also have a client services organization that spans our planners, our strategists, our behind the scenes optimization team, as well as account management. And then outside of that, we also have an entire creative division that really spearheads a lot of this. So out of the 100 people that we talked about earlier in terms of the organization,

**[40:52]** really lean sales team intentionally, but we scale across the other division. So our business ops team is super critical. They're assessing everything and making sure that we're scaling accordingly and appropriately and pacing and all that stuff that you're supposed to do and making really wise business decisions and then like investments in tech or things of that nature. Our client service team is maniacally focused on delivery, performance, creative assessments, ensuring that we are meeting all of our SLAs and timelines and really providing that white glove service. And then I would say the creative and the engineering team

## 41:17 — The importance of operations and data

**[41:34]** are the ones that are really strategizing on if this is a brand, what are they looking for? What could we make pop in the creative? How can we customize it? And then bringing it to life in a way that is gonna achieve the goals of each of the different brands. - I love that. I think there are a lot of CROs that are out there in the market taking on a lot of that work themselves or trying to make decisions without having the right data or infrastructure. And I think just any edge you can get to where you can focus on strategy and everything else is really taken care of, I think just puts you in a position to win. - Definitely.

**[42:15]** I would say I've been fortunate any seat I've sat in from a management perspective, there's always been those departments and they're a secret weapon, but they're also the best weapon because data is a gift. I know I said that about targeting and all of that, but I also mean it on like the output side. We need to have as much information as possible to make the best business decisions. And so those teams feed me the information and I am so lucky 'cause they are absolutely brilliant. - I know you are unbelievably ambitious, you wouldn't be where you are today without being. I'm curious to peek behind the curtain a little bit

**[42:55]** as to the big bets you're making with Big Happy where you're investing in scale and really what you think is gonna help get you there from a go-to-market perspective. - So great question and thank you. We just announced today that we hired a VP of agency partnerships and retail media. So that was just announced and I share that because that leads me to one of the areas that I definitely think is a big bet. On our side, just coming from the retail media background, being at Walmart for connect for five years before coming over here, retail media is massive, it's only continuing to grow and it should grow. It is so powerful and it really does move the needle

**[43:41]** when it comes to getting products off shelves and brand building and e-com sales and all the objectives that a lot of brand marketers and shopper marketers have. There is also this component of offsite media. Offsite media is really great and a lot of the RMS offer this, but offsite media is what drives consumers in store. It is a powerful engine and a lot of RMS have invested in offsite media and I think Big Happy should have a seat at that table. And so we're spending a lot of our time really putting together our go to market for RMS, both for mobile and for digital out of home. On the digital out of home front,

## 44:12 — Big bets for future growth

**[44:24]** we have access to screens and a lot of the different retailers outside of the owned and operated assets that the retailers have. So when you think about a store, there's so much footprint and all of the retailers own certain assets themselves, but there's probably about 10 media owners in the digital out of home space that have access to screens, whether it's in pharmacies or retailers or niche ones like pet stores, for example. And we have access to all that in aggregate. So I feel from a digital out of home perspective, we could absolutely be a compliment to those strategies and RMS can partner with us on that 3D element

**[45:02]** to bring to life all that creative in a way that's gonna resonate and be memorable, so that they're reaching shoppers in the right mindset, using memorable creative that's gonna serve dual purposes, moving units, but also driving brand awareness and recall. We can help fill that void or that gap or amplify what's already happening. On the second side for mobile, mobile is the device that's with the consumer at all moments of all days. And so serving high impact creative using the first party data from the retailer and the close-up measurement from the retailer allows you to speak at scale, but personalized, using all that historical purchase data

**[45:47]** to serve the right message to the right consumer, but using creative that is bigger and bolder and not necessarily invasive, but just is something that will stop them in their scroll and allow you to really create this memory loop where they are now, again, building that brand awareness, but also moving units. And so I'm placing a big bet on RMS based on the hire, but also just based on what I know about what is necessary and what is needed. And I feel really confident that that is something that we will see a lot of success in and we're already starting to get a lot of excitement around it. We were just at shop talk meeting with a bunch

**[46:31]** and they showed a lot of interest and they're really understanding the value prop. We were a grocery shop where we started planting some of the seeds, but I do think that is an area of opportunity for us to continue to grow and to be a complimentary partner to them and to continue to feed the ecosystem and bring new consumers and incremental consumers. - Well, I'm very, very excited about where Big Happy has gotten to at this point, where you're seeing the strategy go next. And I think as we start to wrap up, one thing I wanna just dive into a little bit, a lot of people listening to this show are aspiring CROs.

**[47:12]** And I'm wondering if you could speak a little bit just to your career path that you think enable this path and anything they could glean to help them get on the same path as you. - I will say on my side, I've been really fortunate. I've worked at huge organizations and I've also worked at startups and I never took for granted all the opportunities that were around me. And what do I mean by that? If there was a work stream, I raised my hand to work on it. If there was a new go to market, I raised my hand to be a part of it. I always, no matter how young I was to where I am now, I still say yes to a lot of the things that I'm asked for.

**[47:54]** Of course, it's some boundaries because I'm a mom of two kids and I gotta like balance it all. But what I will say is that I like to learn and I'm always curious and I'm okay saying, I don't understand. Please talk to me as if I've never heard of this before. And I think that vulnerability and the human element of just like how I've always led has made it relatable for folks to connect. But also more importantly, there was a lot of people that believed in me and always brought me along for the journey and saw that I am a builder, whether it's again, a startup or a massive organization. They saw that self-starter mindset and that's what kept me going.

## 48:30 — Career insights for aspiring CROs

**[48:40]** I mean, that's the motivation factor for me is how do I continue to learn? I never want to plateau. And if I don't know something, I will do a ton of research and anyone that wants to be a CRO has to know their numbers like the back of their hand, of course, because revenue is important. You have to be willing to fail and test and get that feedback loop from trusted industry thought leaders to make sure that if you're pivoting or making a change, that you get the backing of folks who know a lot, but also trust your gut. I always did and I'm grateful. I think, again, to your point, starting and closing,

**[49:19]** going from Walmart to a hundred person company, Big Happy, I had to teach a lot of people about what Big Happy was. They were like, you're going from here to here, walk us through the why. And I really did a lot of homework to make sure that this was the right choice for me and my family, but also a lot of self-discovery around what excited me and what was I craving and why was I exploring this. And my gut has not led me wrong yet. So of course, do your homework and make sure your gut is fact checked, but also I think raise your hand to learn. It doesn't matter what level you are. There's always opportunities and people really love those

**[49:59]** that are self-starters and motivated and show that eagerness and ambitiousness and the vulnerability. - Well, I really appreciate the authenticity throughout the entire conversation. I think it's so exciting moving from Walmart Connect to Big Happy, building an offering from scratch, taking it to market, beating your expectations, and then moving into the role where you're responsible for the entire go-to-market function. It's a very exciting path that Big Happy is on and I'm excited to follow what you're doing. And I think the thing that'll probably stay with me most is staying curious. And we're living in a world where things are changing

**[50:39]** so much every single day. There is unlimited stuff to learn. So if you're not investing in it in this environment, I don't know where else you would. - Please do, please do. It's okay to ask questions. It's a beautiful thing. - Well, Gabby, thank you so much for being on the podcast. Can't wait to follow your success and I appreciate all the time. - Absolutely, we'll talk soon. Thank you.