---
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

_Gabby Stoller of Big Happy on creative-first ad tech, building a digital-out-of-home division from scratch, and the GM-to-CRO leap_

**Episode 84 · The LeanScale Podcast**  
Gabby Stoller, Chief Revenue Officer, Big Happy · Hosted by Anthony Enrico  
Published May 29, 2026 · Updated July 22, 2026 · 00:51:06  
Canonical: https://leanscale-knowledge-hub.netlify.app/podcast/gabby-stoller-cro-bet-on-creative/

**Topics:** GTM Strategy · Sales Leadership · Brand & Positioning · Demand Generation · AI in GTM


## Executive summary

Gabby Stoller left Walmart Connect — the retail media network of the number-one Fortune company, where she spent nearly five years leading complex CPG and food verticals — to join Big Happy, a sub-100-person, creative-first ad tech platform that's been called 'the Pixar of digital advertising.' Within six months she went from GM of a brand-new digital-out-of-home (DOOH) division to Chief Revenue Officer. Her career spans the full ad stack — Yahoo, The New York Times, Verve, Placed, Vistar Media, and Walmart — giving her a publisher, platform, retail-media, and ad-tech vantage point. LeanScale co-founder Anthony Enrico interviews her on why she made the leap, how Big Happy is winning with a creative-first strategy, and what she learned building and commercializing a division from scratch.

The spine of the episode is a contrarian bet. Most of ad tech has become obsessed with audience precision — first-party and third-party data, hyper-targeted cohorts — while treating creative as an afterthought. Gabby's thesis is the inverse: every ad is a blank canvas, and you should start with what you're trying to say, then match the creative to the audience's mindset and context. The parallel to go-to-market is direct, and Anthony draws it explicitly: as AI floods every channel with near-unlimited content, volume becomes almost irrelevant and the winner is whoever personalizes best and meets the buyer at the moment of intent. The discipline is to be intentional without being invasive — 'contextualized' one-to-many messaging that resonates with many without triggering the creep factor.

The middle of the conversation is a clinic on standing up a new product line fast. Gabby defines DOOH (billboards, urban panels, place-based screens at gyms, malls, and grocery stores, all the way to point-of-purchase), then walks the launch playbook: because Big Happy owns no inventory, first assess and wire up supply partners; launch as managed service to 'fail and win, fail and win' until the pipes are right; open self-serve so brands and agencies can transact themselves; and close the measurement loop to prove impact. The speed is the moat — they slated three months for go-to-market and were live in under 60 days, with self-serve inside 90 to 120. Two other moves made it stick: omni sequential storytelling (pairing DOOH exposure with mobile retargeting) and a heavy internal-education push — series and certifications — before the company went omni to market on January 1.

The back half turns to the operator. Moving from GM to CRO meant combining marketing and sales into one RevOrg, which created a continuous feedback flywheel that ships go-to-market materials fast in response to market questions. Ops is her declared 'secret weapon': a business-operations team (RevOps included), a client-services org obsessed with white-glove delivery and SLAs, and a creative/engineering team — while the sales team stays deliberately lean. 'Data is a gift,' she says, on the output side as much as the targeting side. On AI, her highest-leverage use isn't automation but preparation: aggregate a buyer's earnings, news, and category signals so you walk into every CMO or agency meeting as an expert, because 'there's no excuse to not show up prepared.' Anthony adds LeanScale's own practice — heavy Claude Code users who built custom deep-research agents for exactly this.

The episode closes on the big bet and the career advice. Big Happy is investing in retail media and offsite media (a new VP of agency partnerships and retail media just hired), positioning its 3D creative as a complement to retailers' owned assets across roughly ten DOOH media owners. Gabby's counsel to aspiring CROs: raise your hand for every work stream, stay relentlessly curious, embrace vulnerability ('talk to me as if I've never heard of this before'), know your numbers cold, and trust your gut — but fact-check it. Who should listen: CROs and aspiring CROs, GTM and RevOps leaders, marketing and demand-gen leaders, and any founder or operator building or launching a new product line or division.


## Key takeaways

1. **Creative is the highest-leverage lever — start there, not with the audience** — After years watching teams pour effort into audience precision while creative became an afterthought, Gabby flips the order: every ad is a blank canvas, so start with what you're trying to say and the mindset you're reaching, then let the creative carry it. Using one creative across every carefully-built cohort wastes the media dollars you spent building those cohorts.
   _Why it matters:_ Audit where your team's effort actually goes. If you've optimized targeting to the decimal but run the same asset everywhere, you're leaving ROI on the table — the differentiated message, not the segment, is what gets remembered.
   _For:_ Marketing Leaders, Founders, Revenue Executives

2. **In a noise-flooded world, personalization beats volume — in ads and outbound alike** — Anthony connects Big Happy's creative-first bet to cold outreach: now that AI can produce near-unlimited content, the amount of noise has jumped 100x and volume becomes almost irrelevant. The winner is whoever personalizes best and finds the intent signals that meet the buyer the moment they're ready to hear the message.
   _Why it matters:_ Stop competing on output. Reallocate effort from producing more to tailoring each touch to a specific person's context and moment of intent — that's the only durable edge as AI commoditizes content.
   _For:_ Marketing Leaders, Sales Leaders, RevOps Leaders

3. **Target the mindset, not the individual — one-to-many without the creep factor** — For DOOH, Gabby matches creative to the location and mindset of each screen rather than the person. A pet-owner campaign can run in pet-friendly apartments, pet-friendly hotels, and vet offices — with slightly different creative in each — so it feels contextually relevant to many without the invasive, retargeted 'I saw you checked in here' creepiness.
   _Why it matters:_ There's a spectrum from intentional to invasive. Use signals (screens that over-index, weather triggers like sunshine vs. rain-cloud creative) to stay relevant and memorable while keeping the brand responsible and organic.
   _For:_ Marketing Leaders, Revenue Executives

4. **Launch a new division as managed service first — 'fail and win, fail and win'** — Because Big Happy owns no inventory, Gabby first assessed supply partners, then launched DOOH as a hands-on managed service with a select few trusted beta clients. Running it managed let the team fail and win, fail and win — getting the creative firing and rendered to each media owner's spec — before opening it to self-serve.
   _Why it matters:_ Don't ship a new motion straight to self-serve. Prove the pipes with a managed, high-touch beta so you can absorb failure privately, then productize the repeatable version and let customers transact themselves.
   _For:_ Founders, RevOps Leaders, Revenue Executives

5. **Speed is the moat at a 100-person company — live in under 60 days** — Big Happy slated three months to bring DOOH to market and was live in under 60 days, then broke into self-serve within 90 to 120 — beating every internal benchmark. Gabby credits a 100-person org's ability to react, pivot, and decide quickly, plus a proprietary CGI tech stack that renders and compresses at scale.
   _Why it matters:_ The advantage of staying small is decision speed. Set aggressive benchmarks, protect the ability to pivot, and treat time-to-market as a competitive weapon a larger competitor can't match.
   _For:_ Founders, Revenue Executives, RevOps Leaders

6. **Omni sequential storytelling: pair the big screen with the phone** — Big Happy deliberately kept mobile as an extension of DOOH so it could continue 'the art of exposure' — a brand seen on an out-of-home screen gets retargeted on mobile, where the consumer is at all moments of the day. Building both channels on one tech stack made the omni story a native capability, not a bolt-on.
   _Why it matters:_ Design channels to reinforce each other in sequence rather than compete for budget. The story that continues across screens outperforms either channel run in isolation.
   _For:_ Marketing Leaders, Revenue Executives

7. **Educate internally before you scale externally** — Before Big Happy went omni to market on January 1, Gabby spent all of 2025 with just a couple of people representing DOOH — running internal series, certifications, and 'the rigmarole' so a predominantly-mobile org could credibly sell the new channel. Only once everyone was trained did brands and agencies get access to both channels.
   _Why it matters:_ A new channel fails if the field can't represent it. Invest in certification and a clear roadmap so every seller can carry the story consistently — internal readiness is a prerequisite for external demand.
   _For:_ Sales Leaders, RevOps Leaders, Founders

8. **The triangulated partnership: agency + brand + platform in the room** — Big Happy's strongest motion puts three parties together — the agency that understands the platform and owns strategy/deployment, the brand that lives for creative storytelling, and Big Happy building the creative that lands. With trust built across all three, Gabby calls it 'building something pretty magical,' compounded by measurement.
   _Why it matters:_ Partner-involved deals raise LTV because two companies are invested in and accountable for customer success. Engineer a better-together story where each party owns a distinct role rather than selling around the agency.
   _For:_ Sales Leaders, Revenue Executives, Marketing Leaders

9. **Live mocks beat pitches — bring the brand's own creative to the first meeting** — Because the tech is fast, reps show up to early meetings with a customized mock of the prospect's brand on a phone or an out-of-home screen in 3D. Seeing it live — often barely a week after first contact — produces an immediate 'wow, I actually can do this' that proves the promised speed, personalization, and white-glove service in one shot.
   _Why it matters:_ Where your product allows, replace the deck with a working, personalized demo of the buyer's own brand. A tangible artifact in the room collapses the sales cycle and does the differentiation for you.
   _For:_ Sales Leaders, Marketing Leaders

10. **Moving GM to CRO means fusing marketing and sales into one flywheel** — In the CRO seat, Gabby's RevOrg combines marketing and sales — previously two separate divisions. Connecting them lets the company react to market feedback fast: the questions coming back from clients turn directly into go-to-market materials, creating a continuous, collaborative feedback loop rather than a hand-off.
   _Why it matters:_ If marketing and sales sit apart, you lose speed at exactly the moment the market is telling you what it wants. Fusing them shortens the loop from buyer question to shipped collateral.
   _For:_ Revenue Executives, Sales Leaders, Marketing Leaders

11. **Ops is the CRO's secret weapon — and the sales team stays lean** — Gabby runs a deliberately lean sales team and scales through the other divisions: a business-operations team (RevOps included) that watches pacing and tech investment, a client-services org maniacally focused on delivery and SLAs, and a creative/engineering team. Every seat she's held, ops was 'the secret weapon and the best weapon' because 'data is a gift' — on the output side as much as targeting.
   _Why it matters:_ Don't let the CRO absorb ops work or fly blind. Stand up the ops and client-services muscle that feeds the revenue leader clean data, so leadership can spend its time on strategy.
   _For:_ RevOps Leaders, Revenue Executives, Founders

12. **AI's biggest GTM payoff is preparation, not automation** — Gabby's most-used AI application is meeting prep: aggregate public earnings, news, and podcasts so you walk into a CMO, brand-manager, or agency meeting as an informed expert who can fact-check a distressed brand or a lost SKU. 'There's no excuse to not show up prepared because everything is at your fingertips.' Big Happy's product has used AI in its CGI stack for years, long before the buzzword.
   _Why it matters:_ Before chasing autonomous agents, weaponize AI for research so every rep shows up as an expert. Anthony's addition: build custom deep-research agents (LeanScale uses Claude Code) to standardize call and podcast prep.
   _For:_ Sales Leaders, RevOps Leaders, Revenue Executives

13. **Retail media and offsite media are the big bet** — Coming from Walmart Connect, Gabby is investing Big Happy's growth in retail media networks (RMNs) and offsite media — the engine that drives shoppers in store. With a new VP of agency partnerships and retail media hired, Big Happy positions its 3D DOOH (access across roughly ten media owners' screens) and first-party-data mobile as a complement to retailers' owned assets.
   _Why it matters:_ Retail media keeps compounding because it moves units and builds brand at once. Vendors that can amplify a retailer's owned and offsite media with differentiated creative earn a seat at a fast-growing table.
   _For:_ Revenue Executives, Marketing Leaders, Founders

14. **The aspiring-CRO playbook: raise your hand, stay curious, trust-but-verify your gut** — Gabby's path came from saying yes to every work stream and new go-to-market, staying curious, and being okay saying 'I don't understand — talk to me as if I've never heard of this.' Aspiring CROs must know their numbers cold, be willing to fail and test, get feedback from trusted thought leaders, and trust their gut while fact-checking it.
   _Why it matters:_ Career leverage compounds from volunteering for hard, unfamiliar work and pairing intuition with homework. Vulnerability and self-starter energy are what make senior people bring you along for the next journey.
   _For:_ Sales Leaders, Revenue Executives, Founders


## Frameworks

### Creative-First Advertising (Every Ad Is a Blank Canvas) (07:23)

**Definition:** Invert the usual order of operations: instead of perfecting audience cohorts and reusing one asset, start with what you're trying to say and the mindset you're reaching, then treat every ad as a blank canvas customized to that audience and context.

Gabby argues that spending heavily on first- and third-party audience precision and then running the same creative wastes media dollars. Customizing the message to the moment — upper-funnel vs. a mom in a pediatrician's office vs. a mobile KPI-driven ad — is what drives ROI, and it 'doesn't cost that much more' to do.

### Mindset-Based Targeting (One-to-Many Without the Creep Factor) (10:11)

**Definition:** For one-to-many media like DOOH, target the location and mindset of the screen rather than the individual, and vary the creative per venue-context so it feels relevant to many without being invasive.

A pet-owner campaign runs in pet-friendly apartments, hotels, and vet offices with slightly different creative in each. Using signals — screens that over-index, weather triggers, dwell time, contextual relevancy — keeps it targeted but not hyper-targeted, staying on the 'intentional' side of the line between intentional and creepy.

### Managed-Service-First Launch Sequence (15:01)

**Definition:** Bring a new product line to market in three moves: assess and wire up supply/partners, launch as a high-touch managed service with trusted betas to 'fail and win, fail and win,' then open self-serve, and finally close the measurement loop to prove impact.

Because Big Happy owns no inventory, the managed-service beta let the team get creative firing and rendered to each media owner's spec before productizing. Only after the pipes were proven did they expand to self-serve, then layered on measurement partners (brand studies, foot-traffic, sales-lift) to build an end-to-end platform.

### Omni Sequential Storytelling (Screen-to-Phone) (15:01)

**Definition:** Design channels to reinforce each other in sequence — a brand seen on a digital-out-of-home screen is retargeted on mobile — so the story continues across screens rather than each channel running in isolation.

Gabby calls it 'the art of exposure.' Keeping mobile and DOOH on one CGI tech stack made omni a native capability; brands can start on the big canvas and continue the narrative on the device that's with the consumer at all moments of the day.

### Internal Education Before External Scale (20:26)

**Definition:** Before opening a new channel to market, educate and certify the internal team so everyone can represent it consistently — treat internal readiness as a prerequisite for external demand.

For all of 2025 just a couple of people represented DOOH inside a predominantly-mobile Big Happy, running series, certifications, and a clear roadmap. Only once the whole team was trained and case studies existed did the company go omni to market on January 1, giving brands and agencies access to both channels.

### The Triangulated Partnership (Agency + Brand + Platform) (26:28)

**Definition:** Put three parties in the room together — the agency (strategy and deployment), the brand (positioning and creative appetite), and the platform (the creative that lands) — each owning a distinct role, compounded by shared measurement.

With trust built across all three, Big Happy takes the brand's positioning, lets the agency deploy and strategize, and builds creative that resonates. Anthony reinforces the model with PartnerStack data: involving a partner raises customer LTV because two companies are invested in and accountable for the outcome.


## Quotes

_Speakers inferred from an undiarized transcript — verify before attributing._

> "Walmart Connect was the most incredible experience. I genuinely feel like I got my MBA, and I got paid to work there at the same time."
>
> — Gabby Stoller, The LeanScale Podcast Ep. 84 (01:31)

> "Creative tends to be a bit of an afterthought after spending so much time on audience design."
>
> — Gabby Stoller, The LeanScale Podcast Ep. 84 (02:08)

> "We take that creative-first mindset that every ad is a blank canvas."
>
> — Gabby Stoller, The LeanScale Podcast Ep. 84 (07:23)

> "If you're using the same creative to speak to all those different audiences, what's the purpose?"
>
> — Gabby Stoller, The LeanScale Podcast Ep. 84 (06:44)

> "Great creative is what makes you stand out and minimizes all the fragmentation on that noise."
>
> — Gabby Stoller, The LeanScale Podcast Ep. 84 (13:01)

> "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."
>
> — Anthony Enrico, The LeanScale Podcast Ep. 84 (09:27)

> "There's a spectrum of, this is intentional and this is invasive and creepy — and balancing that is quite an art."
>
> — Anthony Enrico, The LeanScale Podcast Ep. 84 (11:26)

> "Doing it as managed service allowed us to fail and then win, fail and then win, and eventually, just winning."
>
> — Gabby Stoller, The LeanScale Podcast Ep. 84 (16:21)

> "We basically slated three months for go-to-market, and we were live within less than 60 days."
>
> — Gabby Stoller, The LeanScale Podcast Ep. 84 (18:22)

> "Everything we do sits on this proprietary tech stack that lets us render and compress at scale and do it really turnkey. That's our secret sauce, that's our bread and butter."
>
> — Gabby Stoller, The LeanScale Podcast Ep. 84 (22:32)

> "You've got the agency who understands the power of Big Happy, the clients that love creative, and then you have us in the room — all three of us collectively, we're building something pretty magical."
>
> — Gabby Stoller, The LeanScale Podcast Ep. 84 (26:28)

> "There's no excuse to not show up prepared, because everything is at your fingertips."
>
> — Gabby Stoller, The LeanScale Podcast Ep. 84 (38:16)

> "Data is a gift. We need to have as much information as possible to make the best business decisions."
>
> — Gabby Stoller, The LeanScale Podcast Ep. 84 (42:15)

> "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."
>
> — Gabby Stoller, The LeanScale Podcast Ep. 84 (47:12)

> "I'm okay saying, I don't understand. Please talk to me as if I've never heard of this before."
>
> — Gabby Stoller, The LeanScale Podcast Ep. 84 (47:54)

> "Do your homework and make sure your gut is fact-checked, but also raise your hand to learn."
>
> — Gabby Stoller, The LeanScale Podcast Ep. 84 (49:19)


## Practical advice by role

### Founders

- Launch a new product line as a high-touch managed service with trusted betas so you can 'fail and win' privately, then productize the repeatable version and open self-serve.
- Treat decision speed as your core advantage over larger competitors — set aggressive time-to-market benchmarks (Big Happy went live in under 60 days) and protect the ability to pivot.
- Invest in internal education and certification before opening a new channel to market; the field can't create demand for something it can't credibly represent.

### Revenue Executives

- When you take the CRO seat, fuse marketing and sales into one RevOrg so buyer questions turn directly into shipped go-to-market materials — a continuous feedback loop, not a hand-off.
- Keep the sales team deliberately lean and scale through business ops, client services, and creative/engineering; make ops the secret weapon that feeds you clean data.
- Place your growth bets where the market is compounding (for Big Happy, retail media and offsite media) and back them with a targeted hire that signals the commitment.

### Sales Leaders

- Replace the deck with a live, personalized mock of the prospect's own brand when your tech allows — a tangible artifact in the room collapses the cycle and proves the promise.
- Engineer better-together partnerships: get the agency, the brand, and your platform in the room together, each owning a distinct role, to raise LTV and accountability.
- Use AI for preparation first — aggregate a buyer's earnings, news, and category signals so every rep walks in as an expert and earns trust immediately.

### Marketing Leaders

- Start with the message and the audience's mindset, then customize the creative — reusing one asset across carefully-built cohorts wastes the dollars you spent building them.
- Stay on the 'intentional' side of the intentional-vs-invasive line: use context and signals (venue, weather, dwell time) so one-to-many messaging feels relevant, not creepy.
- Design channels to reinforce each other in sequence (out-of-home exposure retargeted on mobile) rather than competing for the same budget.

### RevOps Leaders

- Position ops as the revenue leader's secret weapon: own pacing, tech investment decisions, and the clean data that lets leadership spend its time on strategy.
- Show up where your highest-volume verticals gather (verticalized events like MediaPost Pharma, CES, Cannes, Shoptalk) so educated buyers gravitate to the offering.
- Build custom deep-research agents (Anthony: LeanScale uses Claude Code) to standardize call and podcast prep and embed AI into delivery workflows.


## AI takeaways

**Thesis:** AI's biggest go-to-market payoff isn't automation — it's preparation. It lets every seller walk into a CMO or agency meeting as an informed expert, and inside Big Happy's product it powers creative personalization at scale. The edge goes to teams that use AI to show up more prepared and more human, not to those who use it to blast more undifferentiated content.

- **AI is a meeting-prep superpower** — Aggregate a buyer's public earnings, news, and podcasts before every meeting so you know the business, can fact-check a distressed brand or a lost SKU, and earn trust immediately — 'no excuse to not show up prepared.'
- **Personalization beats volume** — AI floods every channel — ads and cold outbound alike — with near-unlimited content, so noise is up 100x. The winner is whoever personalizes best and meets the buyer at the moment of intent, not whoever ships the most.
- **AI has been in the creative stack for years** — Big Happy's CGI rendering engine used AI long before it was a buzzword; the visible 'AI moment' in GTM is really the prep-and-research layer catching up to what product teams already had.
- **Build your own research agents** — Anthony: LeanScale are heavy Claude Code users who built custom deep-research agents specifically to prep for sales calls and podcasts and to power delivery workflows.

**Agent & automation ideas**

- A pre-meeting research agent that compiles a target brand's earnings, recent news, category trends, and SKU/retail signals into a one-page brief so reps walk in as experts.
- A creative-personalization agent that generates copy, color, and context variants of an ad per venue and audience mindset (e.g., weather-triggered sunshine vs. rain-cloud creative) at digital-out-of-home scale.
- A market-feedback agent that turns recurring client and agency questions into ready-to-ship go-to-market materials, mirroring Big Happy's combined marketing-and-sales flywheel.


## Operations takeaways

### Revenue operations

- **Ops is the CRO's secret weapon.** Gabby has treated business ops/RevOps as her 'secret weapon and best weapon' in every seat — the team that feeds her the data to make the best decisions.
- **Keep the sales team deliberately lean.** Big Happy runs a purposely lean sales team of ~100 total staff and scales through business ops, client services, and creative/engineering rather than sales headcount.
- **Data is a gift on the output side too.** The same 'data is a gift' mindset she applies to targeting applies to operations: maximize information in to make the best decisions out.
- **Fuse marketing and sales into one RevOrg.** Putting marketing and sales in one org creates a continuous feedback loop that ships go-to-market materials fast in response to market questions.

### Pipeline & marketing ops

- **Verticalized events drive pipeline.** Show up where your highest-volume verticals gather (MediaPost Pharma, CES, Cannes, Possible, Shoptalk) so educated buyers gravitate to the offering.
- **Agencies are a force multiplier.** Deep agency relationships plus a trusted brand create a triangulated partnership — agency, client, and platform in the room together.
- **Live mocks close the gap.** Fast tech lets reps bring a customized mock of the brand's own creative to the first meeting, creating an immediate 'I actually can do this' aha.
- **Partnerships raise LTV.** Anthony: involving a partner in the motion raises customer LTV because two companies are invested in and accountable for customer success.

### Customer operations

- **White-glove is the differentiator.** A client-services org of planners, strategists, optimization, and account management is 'maniacally focused' on delivery, SLAs, and creative quality — and treats every account the same regardless of size.
- **Be agnostic on how customers transact.** Offer both hands-on-keys managed service and self-serve (including running in the brand's own omni DSP) so brands and agencies transact the way they prefer — being agnostic accelerates adoption.
- **Educate internally before scaling.** Certify and train the whole team on a new channel before opening it to market so customers get a consistent, expert experience.


## Metrics mentioned

| Value | Metric | Context |
| --- | --- | --- |
| First 20 → 400+ | Walmart food team growth | Gabby was among the first 20 employees on Walmart Connect's food team; it was over 400 by the time she left — her proof she can build from the ground up. |
| 6 months | GM to CRO | She joined Big Happy to build the DOOH division as GM and moved into the Chief Revenue Officer seat within six months. |
| <60 days | Time to market (managed) | Big Happy slated three months to launch DOOH and was live via managed service in under 60 days. |
| 90–120 days | Time to self-serve | After the managed launch, the division broke into self-serve within 90 to 120 days, beating internal benchmarks. |
| ~100 people · 6 years mobile | Big Happy scale | A sub-100-person organization that had operated on the mobile side for six years before adding DOOH. |
| 1M+ screens | DOOH screen access | Big Happy has access to over a million 3D-enabled digital-out-of-home screens across outdoor, place-based, and point-of-purchase inventory. |
| 7,000+ publisher sites | Custom pharma creative reach | Big Happy's custom ISI scroller creative for pharma is accepted across over 7,000 mobile publisher sites. |
| ~10 | DOOH media owners | Roughly ten media owners hold the DOOH screens (pharmacies, retailers, pet stores, etc.) Big Happy can access in aggregate to complement retailers' owned assets. |


## Entities mentioned

- **Big Happy** (company) — Gabby's employer; a creative-first, CGI-powered ad tech platform ('the Pixar of digital advertising') spanning mobile and digital out-of-home. She built its DOOH division as GM and became CRO within six months; ~100 people, six years on the mobile side, omni to market as of January 1. · https://leanscale-knowledge-hub.netlify.app/company/big-happy/
- **Walmart** (company) — Gabby spent nearly five years at Walmart Connect, the retail media network of the number-one Fortune company, leading complex CPG/food verticals and helping build the digital-out-of-home work stream; she was among the first 20 on a food team that grew past 400. · https://leanscale-knowledge-hub.netlify.app/company/walmart/
- **Yahoo** (company) — One of Gabby's early ad-stack career stops before Big Happy. · https://leanscale-knowledge-hub.netlify.app/company/yahoo/
- **The New York Times** (company) — Publisher stop in Gabby's full-ad-stack career. · https://leanscale-knowledge-hub.netlify.app/company/new-york-times/
- **Verve** (company) — Prior employer in Gabby's mobile-advertising background; roughly six former Verve colleagues reunited at Big Happy. · https://leanscale-knowledge-hub.netlify.app/company/verve/
- **Placed** (company) — Location-based ad-measurement stop in Gabby's ad-tech career. · https://leanscale-knowledge-hub.netlify.app/company/placed/
- **Vistar Media** (company) — The 'massive digital out of home organization' where Gabby learned the DOOH fundamentals she used to commercialize Big Happy's division. · https://leanscale-knowledge-hub.netlify.app/company/vistar-media/
- **MediaPost** (company) — Advertising/media publisher with verticalized events (e.g., MediaPost Pharma) that Big Happy aligns with to reach high-volume verticals. · https://leanscale-knowledge-hub.netlify.app/company/media-post/
- **PartnerStack** (company) — Partner management platform; Anthony references its CRO Mike Head and the LTV lift that comes from involving a partner in the go-to-market motion. · https://leanscale-knowledge-hub.netlify.app/company/partner-stack/
- **LeanScale** (company) — Anthony's firm; he cites its childhood-best-friend COO as an example of following trusted people, and its heavy use of Claude Code and custom deep-research agents. · https://leanscale-knowledge-hub.netlify.app/company/leanscale/
- **Gabby Stoller** (person, guest) — CRO of Big Happy, a creative-first CGI ad tech platform; ex–Walmart Connect leader who built the digital-out-of-home division and rose from GM to CRO in six months. · https://leanscale-knowledge-hub.netlify.app/guest/gabby-stoller/
- **Anthony Enrico** (person, host) — Co-founder of LeanScale and host of The LeanScale Podcast. · https://leanscale-knowledge-hub.netlify.app/guest/anthony-enrico/
- **Claude Code** (tool, AI Dev Tool) — Referenced by Anthony ('cloud code') as the tool LeanScale are heavy power users of, used to build custom deep-research agents for sales-call and podcast prep and to power delivery workflows.


## FAQ

**Q: Who is Gabby Stoller and what is Big Happy?**

A: Gabby Stoller is the Chief Revenue Officer of Big Happy, a sub-100-person, creative-first ad tech platform that's been called 'the Pixar of digital advertising' and spans mobile and digital-out-of-home advertising on a proprietary CGI tech stack. She joined from Walmart Connect (the retail media network of the number-one Fortune company), built Big Happy's digital-out-of-home division as GM, and became CRO within six months. Her earlier career spans Yahoo, The New York Times, Verve, Placed, and Vistar Media.

**Q: What is a creative-first advertising strategy?**

A: A creative-first strategy inverts the usual order of operations in advertising. Instead of perfecting audience cohorts and reusing one asset across all of them, you start with what you're trying to say and the mindset you're reaching, then treat every ad as a blank canvas customized to that audience and context. Gabby Stoller argues that running the same creative across carefully-built cohorts wastes the media dollars spent building them, and that customizing the message — which doesn't cost much more — is what actually drives ROI and makes a brand memorable.

**Q: What is digital out-of-home (DOOH) advertising?**

A: Digital out-of-home (DOOH) is advertising on screens in the physical world outside the home. It includes outdoor inventory (billboards, urban panels, bus shelters), place-based inventory (screens at gyms, movie theaters, malls, and grocery stores), and point-of-purchase screens in-aisle. The screens rotate digital ads and can be bought directly or programmatically through SSPs and DSPs. DOOH is a one-to-many medium, so it relies on mindset- and location-based targeting rather than individual hyper-targeting.

**Q: How do you launch a new product division quickly?**

A: Gabby Stoller's playbook: first assess and wire up your supply partners (Big Happy owns no inventory), then launch as a high-touch managed service with a few trusted beta clients so you can 'fail and win, fail and win' until the pipes are right, then open self-serve so brands and agencies can transact themselves, and finally close the measurement loop to prove impact. Big Happy slated three months, went live in under 60 days, and reached self-serve within 90 to 120 — helped by a 100-person org's decision speed and internal certification before going to market.

**Q: How can a CRO use AI to sell more effectively?**

A: According to Gabby Stoller, AI's highest-leverage go-to-market use is preparation, not automation. Before any meeting with a CMO, brand manager, or agency, use AI to aggregate the buyer's public earnings, news, and podcasts so you walk in knowing the business, can fact-check signals like a distressed brand or a discontinued SKU, and earn trust as an expert — 'there's no excuse to not show up prepared because everything is at your fingertips.' Anthony Enrico adds that LeanScale builds custom deep-research agents (using Claude Code) to standardize this prep.

**Q: What's the difference between being a GM and a CRO?**

A: As GM of a single product line (Big Happy's digital-out-of-home division), Gabby Stoller owned that division's strategy and scaling. Moving into the CRO seat meant sitting above the entire go-to-market engine and combining marketing and sales — previously two separate divisions — into one RevOrg. That fusion creates a continuous feedback loop where market questions turn directly into shipped go-to-market materials, and it requires learning the nuances of every market and region rather than a single product's.

**Q: What career advice does Gabby Stoller give aspiring CROs?**

A: Raise your hand for every work stream and new go-to-market, no matter your level; stay relentlessly curious and never plateau; embrace vulnerability by being okay saying 'I don't understand — talk to me as if I've never heard of this before'; know your numbers like the back of your hand because revenue matters; and be willing to fail, test, and get feedback from trusted thought leaders. Above all, trust your gut — but fact-check it with homework.

**Q: What is retail media and why is Big Happy betting on it?**

A: Retail media is advertising sold by retailers using their first-party shopper data — both on their owned properties and through offsite media that drives consumers in store. Gabby Stoller, who came from Walmart Connect, is making retail media and offsite media a growth bet for Big Happy (hiring a VP of agency partnerships and retail media), positioning its 3D digital-out-of-home creative across roughly ten media owners' screens as a complement to retailers' owned assets, plus first-party-data mobile — all aimed at moving units while building brand.


## Timeline

- **00:00** — Gabby's journey: from Walmart to Big Happy
- **05:04** — Creative-first strategy: the heart of Big Happy
- **14:14** — Understanding digital out-of-home advertising
- **20:26** — Building momentum: key strategies for success
- **27:41** — Strategic go-to-market approaches
- **30:45** — The role of partnerships in success
- **31:12** — Transitioning from GM to CRO
- **34:03** — Understanding market dynamics
- **38:09** — Leveraging AI in go-to-market strategies
- **41:17** — The importance of operations and data
- **44:12** — Big bets for future growth
- **48:30** — Career insights for aspiring CROs


## Related episodes

- **Ep. 93: How HubSpot Built a Media Empire** (Jonathan Hunt) — The demand-gen and creative counterpart — building an audience with content, the way Gabby builds attention with creative-first advertising. · https://leanscale-knowledge-hub.netlify.app/podcast/jonathan-hunt-hubspot-media-empire/
- **Ep. 90: Why Your Niche Isn't Niche Enough** (Gary Frazier) — Brand and positioning companion to the creative-first thesis: memorable messaging beats broad, undifferentiated reach. · https://leanscale-knowledge-hub.netlify.app/podcast/gary-frazier-niche-brand-positioning/
- **Ep. 88: Why AI Won't Close Your Biggest Deals** (Michael Kiernan) — Another operator-CRO out of ad tech on where AI helps in GTM and where humans still win — pairs with Gabby's AI-as-prep view. · https://leanscale-knowledge-hub.netlify.app/podcast/michael-kiernan-nextdoor-ai-wont-close-deals/
- **Ep. 89: Why He Left the CEO Seat to Become a CRO** (Alex Wakefield) — A fellow operator-first revenue leader on the CRO path and why operations background is a superpower in the seat. · https://leanscale-knowledge-hub.netlify.app/podcast/alex-wakefield-acuitymd-ceo-to-cro/
- **Ep. 71: From $500M to $10B: The CRO Playbook for Constant Reinvention** (Alex Loktev) — The CRO-playbook companion for leaders scaling a go-to-market engine through constant change. · https://leanscale-knowledge-hub.netlify.app/podcast/alex-loktev-cro-playbook-reinvention/
- **Ep. 95: Why AI Means More RevOps Hires, Not Fewer** (Jimmy O'Halloran) — Deepens Gabby's 'ops is the secret weapon' point — the operator model of RevOps that wins a seat at the table. · https://leanscale-knowledge-hub.netlify.app/podcast/jimmy-ohalloran-new-relic-revops-consumption-revenue/


## Full transcript

_Machine-transcribed and not diarized; speaker attribution is inferred._  
_Transcript only, as a separate file: https://leanscale-knowledge-hub.netlify.app/podcast/gabby-stoller-cro-bet-on-creative/transcript.md_

### 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.


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