What Agencies Still Don’t Understand About Today’s CMO
As part of the upcoming CMO Lab at POSSIBLE (April 27–29 in Miami Beach), I sat down with Nadine Dietz, who is leading the initiative and has spent years working closely with CMOs across the industry through her work at Virtuosi League, Adweek, and Marketers That Matter. The conversation quickly moved beyond the event itself and into something more telling. On paper, the CMO role hasn’t changed. The mandate is still growth, customer, and brand. But in practice, the role is operating in a completely different environment than it was even a few years ago. That gap between what the role looks like and how it actually operates is where much of the friction is today. And it’s also where many agencies are falling behind. The Shift Isn’t Marketing. It’s Enterprise. One of the biggest changes Nadine pointed to is where CMOs are actually spending their time. It’s less about managing marketing execution and more about navigating the enterprise. CMOs today are expected to operate across the C-suite by aligning teams, influencing decisions, and helping define what growth actually means across the organization. That kind of alignment work isn’t always visible, but it’s now central to the role. A major driver of this is AI. Not because of the tools themselves, but because AI decisions don’t live in one function. They impact operations, finance, product, and HR, forcing CMOs into conversations that go well beyond marketing. They’re no longer just running a function. They’re helping shape the system in which the function operates. Why Good Ideas Aren’t Enough Anymore This is where the gap between CMOs and agencies starts to show up. From Nadine’s perspective, the issue isn’t that agencies aren’t capable. It’s that many are still approaching problems in ways that don’t reflect the reality CMOs are operating in. Ideas alone don’t move things forward the way they used to. Strategy can look great on paper, but it breaks down when it doesn’t fit into the broader organization, doesn’t align with other priorities, or can’t scale across teams and systems. In practice, that breakdown shows up in subtle ways. An agency might bring a strong campaign idea, but executing it requires new data flows, coordination across product and sales, or approvals that take months to navigate. The idea isn’t wrong. It’s just not deployable in that environment. And that’s often where momentum dies. CMOs aren’t just asking, “Is this a good idea?”They’re asking, “Will this actually work here?” A Model That’s Starting to Break There’s also a more fundamental shift happening in how work gets done. The traditional agency model: long timelines, structured campaigns, and clearly defined scopes, is under pressure. The pace of change, combined with the expectation for real-time responsiveness, is forcing companies to rethink how they operate. That shift is showing up in team structure as well. More work is being broken into tasks rather than roles. More talent is being brought in on a fractional basis. And more capabilities that once lived outside the organization are being pulled in-house, often supported by AI. For agencies, this creates a different kind of challenge. It’s not just about doing the work better. It’s about fitting into a system that is actively being rebuilt. What the Best CMOs Are Doing Differently What’s becoming clear is that the CMOs gaining traction aren’t just focused on marketing outcomes. They’re focused on alignment. They’re thinking about how decisions are made across the organization, how teams work together, and how to build systems that actually support growth—not just campaigns that aim to drive it. It’s a more complex job than it was even a few years ago. And it requires a different kind of partner. Where Agencies Need to Rethink Their Approach If there’s one theme that came through clearly, it’s this: agencies need a deeper understanding of the environment in which their clients operate. That starts with empathy, but not in the abstract. In practice, it looks like shifting the conversation. Instead of leading with ideas, the most effective agencies are spending more time diagnosing constraints: How do decisions actually get made inside this organization? What would prevent this from working? Where are the bottlenecks likely to be? It also means pressure-testing ideas before presenting them. Not just “here’s what we’d do,” but “here’s how this would realistically get implemented given your current structure.” Because from the CMO’s perspective, time is limited and the margin for error is small. Every initiative has to fit within a broader set of priorities that agencies don’t always see. In many cases, the agencies that stand out aren’t the ones with the boldest ideas. They’re the ones whose ideas actually work inside the system. The Part No One Talks About Toward the end of the conversation, the focus shifted from strategy to something less discussed. People. Teams are being asked to do more with less. Roles are evolving faster than people can adapt. And there’s a constant level of pressure that sits underneath all of it. In Nadine’s view, the mental health impact across the industry is significant and growing. And yet, most organizations are still focused on chasing the next opportunity rather than investing in the people who deliver it. That disconnect matters. Because in a moment like this, the strength of the team is what determines whether any strategy actually works. Why Spaces Like the CMO Lab Are Emerging That shift is also what led to the creation of the CMO Lab at POSSIBLE. The idea isn’t to add more content to an already crowded conference schedule. It’s to create space for CMOs to step back, compare notes, and work through challenges that don’t yet have clear answers. Because that’s the reality right now. There isn’t a clear playbook for navigating AI transformation, organizational alignment, and evolving expectations simultaneously. Most CMOs are figuring it out as they go. And increasingly, the most valuable insights aren’t coming from the
Esi Eggleston Bracey on Leadership, Change, and Doing You
Executive: Esi Eggleston Bracey, Former CMO Company: Unilever Industry: Consumer Goods Company Snapshot: Global consumer brands company Format: CMO Journeys Interview Why It Matters Esi Eggleston Bracey did not set out to become a marketer. She thought she was headed toward a very different future. But once she found brand building, she found the thing that matched how her mind works: solve problems, understand people, create value. That is what makes her journey worth studying. It is not just a story about rising through big companies. It is a story about trusting your own instincts, growing through discomfort, and staying human while leading at scale. For agencies, her view is especially useful because she is clear about where outside partners matter most. That is also why her perspective will resonate well beyond this conversation, including at POSSIBLE, where she will help lead a broader industry discussion about where marketing and agency value go next. Their Path, in Short Esi grew up in Chicago and describes herself as a kid who loved numbers. Math was her favorite subject. She was curious, active, and, in her words, precocious. Her mother was a lawyer and civil rights activist. Her father was a math teacher. Marketing was not on her radar. She calls herself an “accidental executive,” and that feels like the right place to start. She did not map out a career in business or brand management. What pulled her in was something simpler: she loved solving problems, and she loved people. Once she started at Procter & Gamble, the fit clicked. She realized marketing let her connect insight, creativity, and business in one place. Some of her earliest lessons came from small moments that turned into big ones. As a young brand assistant on Comet Cleanser, she looked at the tear tape on the package and saw more than packaging. She asked whether it could help build awareness for a new product. It could. That simple idea became a major driver of awareness. For her, it was an early lesson in what happens when focus, creativity, and analysis meet. That pattern kept showing up. She talked about helping develop Febreze by connecting a real human tension to a business need. She talked about CoverGirl and listening to people who did not feel seen by narrow beauty standards. Across those stories, her approach stayed the same: understand what people need, then build something that answers it in a way that helps the business grow. Her career also stretched her personally. Moving to Geneva while expecting her second child was one of those moments. Leaving the culture of P&G and stepping into new environments was another. She does not tell those stories like they were easy. She tells them as moments of uncertainty. Then she tells you what she did next: she jumped in. Big Themes From the Conversation The biggest theme in her story is growth through challenge. Esi said every challenge is an opportunity for growth. That is not just a leadership line for her. It is how she has moved through both professional and personal change. Scary moments, in her telling, often became the most transformative ones. Another theme is individuality. Early in her career, she realized she had been trying to conform. She thought success meant studying the environment and matching what she saw. Over time, she learned the opposite. One of her clearest principles is, “Do you. It’s your superpower.” She says it simply, but it carries weight because it came from experience. She also talks about energy in a way that feels practical and personal. She said she manages energy, not just time. Time is limited. Energy can be renewed. That tells you a lot about how she thinks. She is not interested only in output. She is interested in what allows people to keep growing, leading, and showing up fully. And throughout the conversation, she keeps coming back to people. Not just consumers in a narrow sense, but whole people with tensions, needs, and desires. Even when she talks about building brands, she talks about helping people first. That is part of what makes her leadership style feel warm instead of abstract. Watch CMO Journeys Interview How They Choose the Right Agency Partners When I asked her how she thinks about agencies, she started by zooming out. The fundamentals of brand building, she said, have not changed. You still have to understand people, create desire, and turn that desire into commerce through reach, engagement, and conversion. What has changed is the ecosystem around that work: the tools, the channels, the speed, the expectations. That matters because it shapes how she sees agency value. In her experience, the most irreplaceable thing agencies bring is ideas and creativity. Not just campaigns. Not just ads. Ideas that can travel. Ideas that connect to culture. Ideas strong enough to live across different voices and formats. That is where she sees real outside value. She was equally clear about what marketers need to own. In her view, the marketer has to be the integrator. The ecosystem is too complex to outsource the full picture. Data, commerce, media, innovation, and creative thinking all have to connect, and the brand owner has to hold that together. Agencies can support that work with media strategy, planning, execution, insights, and intelligence. But support is different from ownership. That is also why she pushes back on the simple idea that AI means cutting agency spend. She does believe there is waste in the system. She does believe productivity should improve. But she separates that from the bigger question. The better question, she says, is this: what creates irreplaceable value for growth, and who is best equipped to deliver it? That is her standard. Agencies that stand out are the ones that challenge the status quo, bring breakthrough ideas, and help translate those ideas into productive growth. The roles may evolve. The need for value does not. What Stood Out What stayed with me most
What Eric Gillin Learned by Following the Biggest Problem
Executive: Eric Gillin, Chief Brand Officer Company: Trusted Media Brands Industry: Community-driven entertainment across streaming, social, web, and print Company Snapshot: Trusted Media Brands is behind names like Reader’s Digest, Taste of Home, and Family Handyman, reaching hundreds of millions through streaming, social, web, and print. Format: CMO Journeys Interview Why It Matters Eric Gillin didn’t chase a straight line. He chased the biggest problem in the room—first in content, then in product, then in revenue. Now, as Chief Brand Officer at Trusted Media Brands, he’s connecting content, product, and distribution while pushing what he calls a “pivot back to brand.” For agencies, his viewpoint is useful because he’s worked in editorial, product, and ad sales—so he’s seen what actually moves work forward. And he’s allergic to shortcuts. Their Path, in Short Gillin breaks his career into three chapters. The first was as a writer and editor. He came out of college wanting to write, got pulled into the first dot-com wave, and went to TheStreet.com as a reporter. With no CMS, he learned HTML and “hand hack[ed] all the content.” He launched websites out of his living room, worked at Maxim, and later served as a digital director at Esquire and Hearst. In that chapter, he learned how to create, edit, and build the tools that help content work in a digital world. The second chapter was product. He went to Condé Nast and asked to work on product for Epicurious. That move blended his content instincts with product thinking and pushed him into a general manager mode—focused on how to run the machine behind the stories. The third chapter was sales. He moved into running sales for a group he’d been part of, then became head of U.S. ad sales at Condé Nast across brands and categories. He didn’t predict that path. But he says it fits his pattern: “I was always sort of going to where the biggest problem was.” Media kept changing, so he kept learning new languages. Big Themes From the Conversation Gillin’s engine is curiosity, but not the flashy kind. Early on, he watched friends get bylines and feel thrilled. He had bylines too, yet he realized he wasn’t “mega interested in being the center of attention.” What excited him was building: launching a site, hosting it, figuring out how systems work. “It felt good to build things,” he says—and that became the pull. He also carries a simple standard from his dad: “No one can take away the work.” Put in the time. Learn the craft. Gillin translates that into a warning against hacks: there are “no shortcuts.” The “cheat code” fades, so you have to come by the work honestly, start with the user, do something special, and then “insist on consistency.” That same steadiness shows up in his leadership style. He calls himself “jargon-free” and “drama-free,” and tells new teams, “I’m not a table flipper.” In a crisis, he leans on what he calls “service management”: “I work for my team. My team does not work for me.” If emotion creeps in, he takes a walk, takes a break, and returns to examine the problem clearly. And he’s blunt about uncertainty. Leading through the pandemic came with “no playbook.” AI brings the same feeling. In his words: “You just can’t depend on the past to get to the future.” Watch CMO Journyes Interview How They Choose the Right Agency Partners When I asked what cuts through when an agency or vendor reaches out, Gillin didn’t lead with credentials. He led with humanity. “Great ideas and brands cut through,” he says. Even with all the talk about measurement, he comes back to a simple belief: “We’re all human. And I think you know a good idea when you see it.” He also meets agencies where the pressure is real. He describes a world where “the math no longer mats out,” where “reach and frequency is broken down,” and where marketing decisions can shrink into spreadsheets. He doesn’t deny the math. He just doesn’t want it to be the whole conversation. So instead of starting with a CPM or KPI, he prefers to start with the audience. “Let’s talk about who you’re trying to reach,” he says, and how you want to reach them—through emotional connection, not just optimization. Otherwise, he warns, you may “get anything other than a spreadsheet back” that you feel good about buying, without changing anything meaningful. He’s quick to spot copy-and-paste thinking, too. He says he often slows work down with questions like, “Why are we doing this? Why are we doing it this way?” Sometimes it’s not a hard no—more like a “speed bump in the parking lot.” But the point is to challenge the comfort of “we always did it this way,” because “what worked yesterday won’t work today.” And if you listen closely, there’s a consistent thread in what he respects: honest work, clear thinking, and ideas that don’t depend on a temporary trick. He’s seen trends come and go. So the agencies that stand out aren’t the loudest. They’re the ones bringing a grounded idea that’s actually built for real people—and then showing they can deliver it with consistency. What Stood Out The most revealing moment wasn’t a framework. It was a cookie exchange. Gillin described a Taste of Home event in Cleveland that “sold out in six minutes.” Three hundred people showed up with cookies to swap, and he laughed at the sheer volume. Then he talked about a “peach cookie,” a Midwestern specialty he’d never seen—made to look like a peach and tasting “just like peaches.” He called it “mind-blowing.” It’s a small story, but it captures his whole approach. He’s chasing the human element: real people, real places, and moments that feel true. Inside Scoop This article focuses on the journey, the leadership philosophy, and how this CMO works with agency partners. To access the exclusive analysis, including priorities, initiatives, and opportunities, become a NextBigWin Pro member.
CMOs Aren’t Stuck on Strategy. They’re Stuck on Decisions.
The Problem CMOs aren’t confused about what marketing should do. They’re stuck on something harder: what to decide right now, with incomplete information and real pressure to move. That’s a different problem — and if you’re an agency showing up with answers to the first question, you’re missing the conversation entirely. The Signal Across my interviews with CMOs, three decisions kept surfacing unprompted. Not as strategic debates, but as live, unresolved friction. Build vs. Partner CMOs with lean teams and PE-backed urgency aren’t asking whether to use agencies. They’re asking what to protect internally versus what to hand off without losing the muscle. The word that came up again and again: speed. Not quality. Not cost. Speed. An agency that can’t articulate how it accelerates results — not just delivers them — is invisible in this conversation. Bets by Market This one is more complex than “localize the creative.” CMOs are trying to figure out how to build an organization that absorbs market-by-market variability without constantly reinventing itself. For a fantasy sports app, variability is compliance-driven — state by state. For a global consumer social platform, it’s safety and culture. The mechanics are different, but the underlying question is the same: do we build one scalable play or multiple? And how do we stay coherent while doing it? AI Meaning Here’s where it gets interesting. CMOs aren’t just choosing tools. They’re deciding what AI is for their company — a productivity layer, a strategic bet, a channel disruptor, or a trust liability. A security company selling deepfake detection sees AI as a category definition problem. A media brand sees it reshaping the traffic economics they’ve relied on for years. When a client says “we want to use AI,” that sentence contains almost no information. The real question underneath it is the one worth asking. Why It Matters These three decisions share a common structure: the CMO knows something has to happen, doesn’t have complete information, and still has to move. That’s not a strategy problem. That’s a decision-under-uncertainty problem. And it changes what an agency should be offering. The Mistake Most Teams Make Walking in with solutions before understanding which decision the client is actually stuck on. Most agencies pitch to the stated problem. But the stated problem is almost never the real one. “We need a new campaign” often means “I’m under pressure to show results and I don’t know which channel to bet on.” “We want to use AI” often means “I need to look ahead without breaking what’s working.” Pitching to the surface locks you into a vendor position. Engaging with the underlying decision is how you get a seat at the table. The Smarter Move Before your next new business or renewal conversation, identify which of these three decisions your client is actually sitting in. Then ask what’s making it hard to decide, not what they need delivered. That question alone will separate you from most agencies in the room. Most are waiting for a brief. You’re showing up as someone who helps them decide. How to Use This The next time a client mentions speed pressure, market complexity, or AI uncertainty, resist the move to solutions. Ask what decision they’re stuck on, and stay there longer than feels comfortable. Signals aren’t permission to pitch. They’re guidance on how to show up with something worth hearing. These patterns come from ongoing CMO and brand leader conversations we share each month with NextBigWin Pro members. If you’d like access to the full briefings, you can learn more here.
Josh Churnick’s Eclectic Path to Practical Marketing Leadership
Executive: Josh Churnick, Chief Marketing OfficerCompany: Vertex Service PartnersIndustry: Residential exterior home services (roofing-led, multi-brand platform)Company Snapshot: A platform of regional brands supported by shared servicesFormat: CMO Journeys Interview Why It Matters Josh Churnick didn’t take a straight line into the CMO seat. His path runs through very different worlds, and it shaped a leadership style that’s both creative and deeply practical. He talks about marketing as a craft you can measure—because the customer always tells you what’s working. And for agencies, his viewpoint is refreshingly direct: he’s clear on what earns trust, what breaks it, and what a real partnership actually requires. Their Path, in Short Josh describes his career as “eclectic” until he found the lane that fit. Early on, he wasn’t trying to become a “home services marketing guy.” He was trying to become a better marketer—period—by learning different categories and different ways customers make decisions. One of his earliest chapters forced him to learn the basics in a hands-on way. After high school, he built a digital platform for independent music artists. The idea was simple: give artists a place to create profiles, share show dates, and grow an audience. He partnered with Billboard magazine and worked around performance venues connected to that ecosystem. It wasn’t a neat corporate role with a neat job description. It was the messy kind of work where you learn what people care about because you have to earn attention. From there, he moved through a mix of industries—entertainment, consumer packaged goods, restaurant groups, and insurance—building a broader sense of what makes marketing click. Over time, he noticed he was drawn to roles where the feedback loop was clear. He liked being able to set up tracking, run a campaign, and see the results plainly—“in black and white”—instead of having performance judged by taste or office politics. That preference eventually led him into home services, where response can be direct and attribution can be tight if it’s set up correctly. For Josh, that environment made marketing feel honest. If something works, you see it. If it doesn’t, you see that too. And that’s where his voice as a leader sharpened: do the creative work, yes—but let reality decide. Big Themes From the Conversation Josh sees marketing as the bridge between what a company offers and what a customer needs. When marketing is great, it doesn’t just “look good.” It communicates value in a way a consumer understands and acts on. That’s why he keeps circling back to the balance of art and science. Creative matters. Messaging matters. But he doesn’t treat creative like a mystery that can’t be tested. He talks about trying things, comparing performance, and learning through outcomes. The goal isn’t to win an internal argument about what’s best. The goal is to find what customers respond to. A mentor’s advice helped lock in that mindset: don’t worry about what you like—worry about what works. Josh repeats that because it’s a trap he’s seen again and again. Teams fall in love with their own ideas. They chase the “cool factor.” And then they confuse their preferences with the customer’s reality. He also talks about personal growth in a way that feels honest. Earlier in his career, he admits he cared too much about how “cool” the brand seemed. Over time, that changed. Now he defines success by impact: if marketing helps the business run better, helps the teams downstream perform, and supports the people doing the work, then marketing is doing its job. Even when he touches on technology like AI, he frames it as exactly what it is: a tool. Useful, powerful, worth exploring—but not a replacement for judgment. In his view, marketing still needs people to guide it because marketing is still aimed at people. Watch CMO Journeys Interview How They Choose the Right Agency Partners When I asked Josh what makes an agency relationship work, he didn’t start with awards or big names. He started with behavior—and he didn’t point the finger only at agencies. His philosophy is that agencies are extensions of a marketing team. That means partnership has to be real, not performative. And the first test of “real” is transparency. If an agency is expected to drive leads, then the client has to share what happens to those leads. Without that, the agency is flying blind. Josh’s clearest example is disposition data—what happens after the lead comes in. Did the lead convert? Did it not convert? What were the common reasons? If the client withholds that information, then optimization becomes guesswork. In his view, that’s a fast way to create frustration on both sides: the agency can’t improve what it can’t see, and the client can’t get better results from a partner it refuses to equip. He also has a sharp definition of credibility: outcomes. In home services, he says, attribution can be very clear when tracking is built correctly. That means performance can’t hide behind pretty reporting. Results show up—or they don’t. So when agencies talk about expertise, Josh listens, but he ultimately checks whether the work drives measurable impact. That’s why he’s cautious about “category claims.” Some agencies say they know home services, but when you look closer, their experience is thin or short-lived. Josh doesn’t say agencies can’t learn. He’s saying the learning curve can be expensive if the client becomes the training ground. At the same time, he doesn’t want partners who only know one world. Josh credits his own mixed background with giving him ideas he can apply in new places. He values a partner with range—someone who can bring in outside lessons without losing respect for the category’s realities. But range alone isn’t enough. He’s wary of agencies that feel “all over the place,” because they may not understand the mechanics that matter in a performance-heavy environment. The best partners, in his telling, combine real proof with real curiosity: they show they understand the category, and they show they’re still
How Sarah Cascone Leads With Clarity Under Pressure
Executive: Sarah Cascone, Chief Marketing OfficerCompany: Appriss RetailIndustry: Retail technology (returns, fraud, profit protection)Company Snapshot: Helps large retailers reduce fraud, manage returns, and protect profit across in-store and online channels.Format: CMO Journeys Interview Why It Matters Sarah Cascone didn’t plan on a marketing career—and that’s why her perspective feels grounded. She learned marketing through live rooms and real conversations, then carried those lessons into SaaS and enterprise retail tech. Now, as the first CMO at Appriss Retail, she’s clear about what earns trust and what wastes time—especially with agencies. Their Path, in Short Sarah grew up in Brooklyn and studied psychology in college. She once thought she’d become a criminal psychologist, but chose a different path because that work felt too depressing day to day. Instead, she poured herself into events and conferences. At Worldwide Business Research, she learned how to plan and execute a conference from the ground up—connecting messaging, experience, and audience. Then she moved into SaaS and joined Bluecore in its early days. Over time, she expanded her scope from events into PR, content, design, demand gen, and product marketing—until she was running the full marketing function. That shift was defining: marketing couldn’t be separate activities. It had to operate as one engine, embedded with sales and customer success, with shared goals and accountability. Now she’s applying those lessons at Appriss Retail in a more complex enterprise context. Big Themes From the Conversation Sarah has a simple belief about speed: “Speed forces clarity.” Under revenue pressure, she said, you don’t have time for confusion or “politeness theater.” Direct communication becomes an efficiency strategy—clear feedback, tough conversations, fast decisions. Her events background still shapes her filter for what works. Events taught her pattern recognition—what lands, what doesn’t, and why. But they also anchored her in something more basic: everyone is selling to a human being. Being memorable, real, and trustworthy isn’t extra. It’s the foundation. And she uses a blunt test: if your message doesn’t work in a live conversation, it won’t work in a campaign. She’s also decisive about “no.” She pushes back on brand-versus-demand debates because she sees them as a false binary. She says no to work that doesn’t move pipeline, accelerate it, or expand it—and she says no to shiny objects without a clear business case. Watch CMO Journeys Interview How They Choose the Right Agency Partners When I asked Sarah what gets her attention from an agency, she didn’t talk about a portfolio. She talked about a point of view. She wants agencies to lead with perspective and evidence that they understand her business model. She said she gets too many pitches built for SMB or mid-market motions, even though she operates in enterprise. That tells her the agency didn’t do the work—and it signals a lack of respect for her time. That same respect-for-time lens shapes who should be approached first. Sarah’s view: It depends on the size of the problem and how tactical it is. If an agency is pitching something that clearly sits with someone else on her team, going straight to the CMO can feel misaligned. But if the problem is truly significant, then it makes sense to reach higher. Match your ask to the scale of impact. What separates great partners from the ones that struggle? Sarah said great agencies become an extension of her team—comfortable embedding not only with marketing, but with the broader org, and even working across leaders like the CRO and CPO. They understand strategy deeply, and the work reflects it. Most importantly, they reduce her cognitive load. They don’t create more decisions. They remove them. She described her marketing team as two pillars: product marketing, which tells the story in market (including content and thought leadership), and growth marketing, which distributes it (including outbound and events). And then there’s her favorite way to build credibility: executive conversation. Sarah described creating owned community moments for VPs and above—behind-closed-door strategy discussions that include customers and prospects, plus subject matter experts outside her company. The goal is to keep a real conversation going between major industry events, so the next step isn’t always “take a sales meeting.” It’s: add value without obligation, and earn the right to go deeper. She also chooses partners with intent. She works with a content agency, StoryArb, because they’re strong at editorial, subject-matter-expert-driven playbooks and newsletters—“the kind of content people actually want to read.” She also works with a retail-focused PR agency to extend the story through press releases, bylines, commentary, awards, and interviews. Agencies can learn from her community approach. Curated roundtables can build trust in a way cold outreach often can’t. That’s also why Next Big Win runs an Executive Access Program—executive roundtables designed to help agencies and partners build relationships with senior leaders through candid, small-group conversations. Learn more here. What Stood Out Sarah’s mix of intensity and self-awareness is striking. She talked about what it feels like to “shoulder an entire function,” and how that requires a personal operating rhythm that’s sustainable. She also named a hard unlearning: assuming she knows better than the person in front of her. That openness—paired with her speed—is a rare combination, and it says a lot about how she leads. Inside Scoop This article focuses on the journey, the leadership philosophy, and how this CMO works with agency partners. To access the exclusive analysis, including priorities, initiatives, and opportunities, become a NextBigWin Pro member.
Scaling Business Development Beyond the Agency Founder
At most agencies, “scaling BD” looks like this: the founder hires a Head of Business Development, hands them a vague mandate to build pipeline, and hopes the problem goes away. Six months later, the pipeline is thin, close rates are bad, the founder is back in every deal, and the hire is gone. I’ve watched this happen across countless agencies I’ve advised, and I’ve done it myself. The instinct to find one person who can take over BD makes sense on paper. But it almost never works, because the problem isn’t the hire. It’s that you’re trying to outsource something you haven’t even broken apart yet. The Founder Is Wearing Five Hats When a founder says they “do business development,” what they really mean is they’re doing five or six jobs at once under one label. They’re working events. They’re posting on LinkedIn and sending the newsletter. They’re keeping up with referral partners. They’re running discovery calls and writing proposals. They’re upselling existing clients. It works because the founder is scrappy and has good instincts, but it’s held together with scotch tape and none of it is getting more than 20% of the attention it needs. You can’t just hand that to someone. The job as it exists today is five jobs. Nobody you hire is going to seamlessly bounce between brand-building, partnerships, prospecting, sales, and account expansion the way a founder does. So the founder’s real job isn’t to find a replacement. It’s to take the work apart. The Five BD Functions After spending years talking to agency founders, fractional BD consultants, and sales leaders, and going through our own experience at Barrel Holdings, I’ve started thinking about agency BD as five separate functions: Marketing and Awareness is the long game. Content, LinkedIn, newsletters, conferences, webinars. All the stuff that keeps you top of mind so when a prospect has a need, they think of you. Some of this may stay with the founder for a while, especially thought leadership. Partnerships is about cultivating referral relationships with other agencies, consultants, and platform ecosystems. It’s relationship management, not sales. It has its own rhythm that includes check-ins, co-marketing, and mutual referral loops. From my BD observations, this kept coming up as the thing that moves the needle most, especially when your agency’s tight positioning makes it easy for partners to send opportunities your way. Outbound is cold email, LinkedIn outreach, direct mail. A targeting-and-volume discipline that needs its own process, its own lists, and constant iteration on messaging. It requires a special set of skills and it’s bound to struggle when you lump it together with inbound. We’ve experienced this firsthand and it’s something I heard over and over from experienced BD folks: split inbound and outbound, even if one is just a part-time role. The Sales Process covers everything that happens once a real opportunity shows up — discovery calls, framing the problem, scoping the engagement, building the proposal, negotiating, and getting to a signed contract. For most founders, this is where their credibility and trust matter most, which is why they’re so reluctant to let go. But the sales process isn’t one monolithic job. Qualification alone could be its own role — someone managing inbound referrals, running the initial discovery, researching the prospect, and determining fit before the broader team gets activated. Scoping might pull in a solutions consultant or subject matter experts from across the agency. The proposal itself can be a team effort. The founder doesn’t need to own every step; they just need to show up at the moments where their presence tips the deal. Account Growth is upsells, cross-sells, and expanding existing client relationships. This is probably the best ROI BD activity and the one most agencies often overlook. You already have the trust. The question is whether you’ve actually designed what comes next after the initial project. Get the Sequencing Right Most founders get the order wrong. They want to hand off outbound first because it feels like the grind. But outbound without positioning, proof points, and case studies just doesn’t land. Here’s the order that’s worked for us and for the agencies I’ve talked to: Start with Account Growth. You already have people in client relationships such as account managers and project managers. Make account expansion part of their job description. Design the path after the core project. Give them ownership and variable comp for growing accounts. You’re monetizing relationships you’ve already earned. Then Partnerships. Investing in a dedicated partnerships lead who knows the ecosystems your agency plays in can really pay off. While you may not get opportunities right away, monitor the inputs (co-marketing, sending opportunities to other partners) and let the relationships take root. Then Marketing Execution. Hire someone to own the content calendar, post consistently, manage the newsletter, keep the website updated. The founder still brings the ideas and the point of view, but the week-to-week execution is off their plate. This is what builds the top-of-funnel engine that feeds everything else. Encourage other qualified members of the team to contribute and develop an authoritative voice as well. Then Outbound. Only once you have the positioning, the case studies, and the proof points that give cold outreach some teeth. You might invest in a GTM engineer or work with an outbound specialist agency. The sales process comes off the founder’s plate last. It’s what they’re best at and what’s hardest to transfer. But remember, you don’t have to hand off the whole thing at once. Start by peeling off qualification and scoping to people on your team. Let an account exec handle the early stages while the founder weighs in with insights and key appearances to help close. Over time, maybe 80% of opportunities can be run end-to-end by a BD manager, and the founder only steps in for the high-stakes deals where their presence really matters. One thing worth calling out: you’ll be tempted to bundle a few of these functions into one hire.
Winning in AI Search: What Marketers Need to Know Now
AI-driven search is no longer a future trend—it’s already reshaping how brands are discovered, evaluated, and ultimately chosen. In this session, Winning in AI Search, NextBigWin partnered with Crossfill and Tap In Digital, alongside Michele Hsu (VP of Marketing at Cerebro Capital), to break down what’s changing—and what marketers need to do about it. View the full presentation deck The Shift: From Rankings to Recommendations One of the biggest takeaways is simple but important: AI doesn’t rank. It selects. Traditional SEO focused on rankings, clicks, and traffic. But AI-generated answers skip that entire process. Instead of showing a list of links, platforms like ChatGPT and Google AI Overviews recommend a small set of brands directly. In many cases, 60–80% of recommendations are concentrated among just three brands. If you’re not included, you’re not just lower—you’re invisible. The New Problem: Invisible Demand AI is creating a layer of demand that most companies can’t see. No impression No click No attribution As highlighted in the session, a user can discover your brand through AI, then visit directly, while your analytics show “Direct” traffic and give AI zero credit. This creates what Tap In Digital calls a “dark demand layer” —influence that exists but isn’t measured. What to Measure Instead The session introduced a new set of metrics that matter in AI-driven discovery: Brand share of voice in AI answers Citation frequency Prompt coverage (where you show up vs. don’t) Competitive inclusion gaps These signals determine whether your brand is even part of the consideration set. From Visibility to Revenue This is where the partnership between Crossfill and Tap In Digital becomes powerful: Crossfill helps companies measure and improve AI visibility by tracking how often brands appear in AI-generated answers and recommendations. Tap In Digital helps connect that visibility to revenue, bringing AI signals into attribution models and media mix frameworks to quantify real business impact. Together, they close the gap between: “Are we showing up?” and “Is this driving growth?” Partner Offers To help teams get started: Crossfill is offering a Free AI Visibility Audit For agencies: 1–2 client accounts For brands: benchmarked vs. top 3 competitors Contact: sales@crossfill.com Tap In Digital is offering an AI Revenue Mapping Sprint Connect AI visibility signals to downstream revenue First 10 attendees receive 50% off Contact: kirk@tapindigital.com The Bottom Line You are already losing share in AI-driven discovery. You just can’t see it yet. The brands that start measuring—and acting—now will be the ones that win.
Ethan Chernofsky and the Value of Staying Uncomfortable
Executive: Ethan Chernofsky, Chief Marketing Officer Company: Placer.ai Industry: Location analytics Company Snapshot: Placer.ai helps brands, retailers, real estate players, and investors understand what is happening in the physical world through location analytics. Format: CMO Journeys Interview Why It Matters Ethan Chernofsky did not build his career in a straight line. His path moved through agency work, public relations, strategy, and then into in-house leadership, where the stakes got bigger and the learning got sharper. That makes his story worth studying because it shows how a marketer can grow by chasing discomfort instead of avoiding it. It also makes his perspective useful for agencies. He has been on both sides of the table. He has pitched. He has been pitched. He knows what feels thoughtful, what feels forgettable, and what makes someone worth calling when the timing changes. Their Path, in Short Chernofsky describes himself as a regular kid from Pennsylvania. He played baseball, did well in school, and grew up with parents who made sure he stayed on track. But what stayed with him most was a fascination with people dynamics. He became interested in how people make decisions and what shapes behavior, which later became a core part of how he thought about marketing. He left home young, spent time in different places, and eventually built his career in Tel Aviv’s tech ecosystem. Once he got into that world, he says, one opportunity kept leading to another. He started on the agency side in public relations, working with companies including Wix, Lightrix, and Lemonade. That work gave him a rare vantage point. He got close to many companies at once and learned by watching how different leaders thought. He could see what strong storytelling looked like, what smart positioning sounded like, and how different businesses approached growth. But over time, he wanted something more. He did not just want to advise from the outside. He wanted to own the work more fully. The move in-house felt intimidating. He says that plainly. It was not just a new title. It was a new way of operating. Agency life had taught him pace and range. In-house life demanded depth, patience, and a willingness to listen. At Similarweb, he says, he had to learn from people who were already doing the work at a high level. Sometimes that meant talking less and absorbing more. That mindset stayed with him. Across each step, he seems to have been drawn less by comfort and more by the chance to stretch. He does not frame growth as a smooth climb. He frames it as entering rooms before you feel fully ready, then learning fast once you are inside. Big Themes From the Conversation One of the clearest themes in the conversation was his relationship with discomfort. Chernofsky says the fear never really goes away, and he does not think it should. To him, that tension is part of growth. If you feel completely settled all the time, you may not be pushing yourself enough. He had a striking take on imposter syndrome. He said he does not see it as a syndrome at all. He sees it as real. Every new challenge asks you to do something before you feel fully qualified to do it. In his mind, that is not a warning sign. It is the cost of getting better. Another theme was curiosity without ego. He says you can learn from everybody, both the people you admire and the people you do not naturally connect with. Some people teach by example. Others teach by showing you what not to do. Either way, he believes there is value in paying attention. He is also wary of simple labels. His view of the “full stack marketer” idea is direct: most people are not great at everything. They are strong in some areas, weaker in others, and always still learning. The important part is being honest about that. Know your strengths. Know your gaps. Keep moving anyway. Running through all of it is a sense of fascination. He talks about being energized by things he does not fully know yet. That may be one of the best clues to how he operates. He does not lead with certainty for the sake of appearances. He leads with curiosity, enthusiasm, and a willingness to test ideas in public. Watch CMO Journeys Interview How They Choose the Right Agency Partners When I asked how he thinks about outside partners, his answer was balanced. His natural instinct leans internal. He likes having people close to the brand, living it every day. But he also sees the value of agencies when the match is right. The way he explains it is simple. Internal people bring depth. Agencies bring range. One person may know the business inside and out. An agency can bring multiple perspectives, more category exposure, and lessons from other companies and markets. So the question is not whether one model is better than the other. It is where the value shows up for the work that needs to be done. He used PR as a strong example. Placer.ai has worked with an external agency for years, and he pointed to the benefits clearly. The agency brings a broader market view and experience across multiple interests. But he also pushed back on the idea that bigger always means better. In that case, they did not want the largest shop. They wanted the right one. That idea shaped how he evaluates agencies more broadly. He thinks too many companies ask who did great work for someone else and treat that as enough. He believes the better question is whose model fits what you actually need. Sometimes that is a boutique agency. Sometimes it is a much bigger team. Size does not prove fit. Alignment does. He was just as clear about what gets his attention. Multi-channel outreach can work, he said, but only if the message is strong. Generic outreach does not land. Volume
How Adriana Gil Miner Leads Through Discomfort and Change
Executive: Adriana Gil Miner, Chief Marketing OfficerCompany: PindropIndustry: Digital communications security (fraud, deepfakes, authentication)Company Snapshot: Enterprise platform helping detect deepfakes, prevent fraud, and restore trust across contact centers and virtual meetingsFormat: CMO Journeys Interview Why It Matters Adriana Gil Miner is the kind of marketer who runs toward uncertainty. She’s Chief Marketing Officer at Pindrop, working on a trust problem: when voice and video can be faked, how do people know what’s real? Her story is worth studying because she blends the discipline of data-driven marketing with the power of storytelling. For agencies, she offers a practical view from both sides of the table. Their Path, in Short Gil Miner breaks her career into chapters. The first was early digital marketing, when e-commerce was maturing and measurement was still catching up. At Digitas, she worked with American Express and took over an affiliate program that became the company’s number one acquisition channel. That work also pulled her into product problems — moving communications from old systems into digital. The second chapter was a pivot into brand and storytelling. As user-generated content began to reshape how information spread, she moved to Weber Shandwick and learned what she calls the “incredible power of storytelling.” One client she supported during that period was Tableau. Later, she joined the company and focused on brand building and community — work that also tied into Tableau’s data storytelling and data journalism efforts. Her current chapter merges those worlds: the science of technology and the human craft of narrative, applied in high-growth environments where change is constant. Watch CMO Journeys Interview Big Themes From the Conversation She treats discomfort as proof of growth. Every leap, she says, makes her uncomfortable, and if she isn’t uncomfortable, she isn’t growing. So she builds a career (and a team) around learning fast. She also lives by advice from former Tableau CMO Elisa Fink: “people are the plan.” To Adriana Gil Miner, marketing isn’t a set of tactics. It’s what capable people can build together, especially when the tools and the market keep moving. Pindrop’s Story Pindrop’s work starts with a hard truth: it’s getting harder to trust what you hear and see. Gil Miner says deepfakes aren’t just celebrity headlines. It can take seconds of someone’s voice to generate a convincing fake, and video is getting harder to verify, too. When voice and video can be copied, the usual identity checks stop working. Fraudsters impersonate customers and call retailers to push through refunds — “$20, $30 at a time” — then scale it with bots. It’s not a niche problem: Pindrop’s 2025 Voice Intelligence and Security Report notes retail fraud surged +107% from 2023 to 2024 (reaching 0.79% of calls as confirmed fraud), and the team forecasts it could climb to 1 in every 56 calls. Or they impersonate a family member and drain bank accounts — another channel where phone-based attacks keep rising, with fraud at U.S. banks occurring in 1 out of every 650 calls and up +61% cumulatively since 2020. That pattern is why Pindrop’s work has started showing up in public-facing moments, not just behind-the-scenes security stacks. In this Al Jazeera segment, CEO Vijay Balasubramaniyan breaks down how quickly deepfakes are getting cheaper and more convincing — and why humans are already bad at spotting them. It’s a useful lens on the same trust problem Gil Miner is focused on: when a fake voice can trigger real-world outcomes (from stolen refunds to election misdirection), the “verify first” mindset stops being a nice-to-have and becomes table stakes. How They Choose the Right Agency Partners When she stepped into the CMO role, she says the priority was to “get the message out about the problem.” This is white space — there aren’t “deepfake budgets,” and buyers don’t always have language for what they’re facing. So her job is to “sell the problem” first, because the public needs to understand that “you and I are at risk.” Of course, awareness isn’t the only scoreboard. Leaders still want pipeline, and they still ask for predictability. Her answer is a three-part go-to-market “stool.” One leg is awareness. She talks about showing up inside communities and social channels, plus channels like podcasts and out-of-home that build word of mouth. The second leg is direct pipeline: a strong ABM program that blends outbound SDR work with LinkedIn and digital performance. She adds a line that feels like her whole philosophy: digital is “more like a cat.” When someone is interested, you can catch it. To create momentum, she leans into events because events put “people in front of people.” The third leg is partners. Pindrop is “very partner-heavy,” she says, embedded in platforms like Zoom, Webex, and Microsoft Teams. For her, partners aren’t a checkbox. They expand distribution and selling routes, and she describes increased investment in marketing and selling with them. That operating model shapes how she works with agencies. Internally, her team is lean — about 20 people — organized into brand and community (plus customer marketing), product marketing, and a demand-gen engine that includes integrated campaigns, martech, and events. She’s also restructuring for an AI world, with an initiative to “democratize creative,” where everyone in marketing is expected to be their own writer and designer, supported by tools and training. Externally, she uses agencies, consultants, and fractional talent. She says an outside view helps organizations move faster. But she’s clear about where agency value is going. AI can replace a lot of production, she says. Execution isn’t the differentiator. The differentiator is strategy, clear goals, and the ability to guide transformation — helping teams adapt when old habits break, and when messy realities like legacy data get in the way. So what makes an agency stand out? Understanding. She says her inbox is packed with outreach, and most of it sounds the same. The agencies that win “deeply understand you.” They do real research, bring intelligence, and teach her something. What falls