The Agency Lifecycle: Why Your $10M Strategy Will Kill Your $1M Business
There’s a myth in agency land. That growth is linear. The assumption goes like this: If you hustled yourself to $1M, you hustle 10x harder to get to $10M. Founders can imagine the revenue chart as a smooth line, up and to the right. More leads. More bodies. More hours. This is what I refer to as the Linear Growth Fallacy. If you study the path of successful agencies, as I did with nearly 70 founders who’ve grossed hundreds of millions in revenue, then the growth isn’t linear. It is a step-function. The “operating model” needed to run a $1M agency and the “operating model” needed to serve a $10M agency are different. In fact, they might be different companies altogether. Ryan Watson of Upsourced, who scaled one agency to $45M, describes this as Lifecycle Modeling. Paul Wilson, who helped sell his $30M agency to Merkle, calls it “breaking the ceiling.” The central thesis remains the same: The strategy that is your rocket fuel at Stage 1 becomes your anchor at Stage 3. You’re not only required to grow; you’re required to evolve in order to survive. This is my GTM framework outlining the four distinct stages of agency maturity, as well as the “brick walls” that define them. Stage 1: Validation ($0–$1M) The Hustle Operating Model. In its early stages, you don’t have a business; you have a hypothesis that you and your team must validate with cash. The pivotal characteristic of this stage is existential anxiety. You’re fighting for oxygen nonstop. Many founders succumb to this anxiety by “playing business.” They spend weeks designing logos, 5-year strategic plans, or building complex HubSpot automations. This is “fake work.” It looks like it is productive work, but has no value in terms of asset value. The Strategy: At this stage, the founder is the product and the sales channel. Asset type: personal reputation Key metric: cash flow Mason Cosby, founder of Scrappy ABM, demonstrates that very well. He completely disregarded the “agency playbook.” He didn’t wait for a brand deck. Using a high-friction, unscalable approach, podcasting, and direct networking, he successfully produced $4.5M in pipeline with $0 ad spend. Stage 1’s rule is pretty simple: Your 80% time is spent on sales and delivery. If you are automating a process you haven’t sold yet, you are just playing business. Stage 2: Standardization ($1M–$3M) The “Positioning” Operating Model If the theme of the first stage is saying ‘Yes’, the theme of the second is saying ‘No.’ You have survived the hustle by now, yes. You have revenue. But you are probably in the “Generalist Trap.” You arrived here by taking every single client request, which means your delivery team is reinventing the wheel every week. You don’t establish a system for “we do whatever you want.” The Brick Wall: The founder is the bottleneck; you hit a revenue ceiling. You wear 1,000 hats, and no one can replace you with a new one due to “process,” which lives in none other than your head. The Strategy: You’re moving from a service business to a productized firm. Travis McAshan of Glide notes that a great example of real expertise is being able to drop 20 insights off the cuff. Generalists can’t do that. If you want to scale past $3M, you need to embrace Ruthless Positioning. By focusing (as Ben Zettler did with his ecommerce ecosystem), you can standardize your delivery. Standardization generates an asset, a process that transcends the brain of the founder. Stage 3: Delegation ($3M–$10M) The “Management” Operating Model This is the agency “Valley of Death.” Between revenues of $3M–$4M, a “Brick Wall” emerges, Ryan Watson argues. The informal communication structures that worked for a team of 10 disintegrate at a team of 30. Quality slips. Culture frays. Old employees start to resent new hires. Now, the mistake founders make here is applying Stage 1 logic (work harder) upon a Stage 3 problem (complexity). The Strategy: They need to establish a Second Layer of Leadership. You are no longer pitching projects. Instead, like Adam Kurzawa says, you’re selling enterprise value instead. This involves moving from “Founder-with-Helpers” to “Company-with-Departments.” You need to bring on high-priced management layers that will temporarily weigh on your margins. This feels bureaucratic. You are losing the “soul” of the agency. But unless you are able to add this layer, the founder is the bottleneck, and the business effectively becomes unsellable. Stage 4: Liquidity ($10M+) The “Engine” Operating Model At $10M+, your difficulty transforms from delivery to volume. To simply stay flat, you would have to replace $2M–$3M in churned revenue annually. You are feeding a beast. The peril here is commoditization, turning into a “vendor” who competes on price instead of a “partner” who competes on value. The Strategy: You need to have that revenue decoupled entirely from the founder. Paul Wilson, who took his agency to a $30M exit, states that a founder must move from the “Closer” to the “Brand.” The business must have a Diversified Sales Engine: a combination of inbound, outbound, and partnerships operated by a specialized CRO. At the end of the day, Private Equity firms pay for “Engines,” not “Hustlers,” in terms of premiums. If the revenue stops when the founder leaves the room, you don’t have a business; you have a high-paying job. The Mental Model: Act Your Age The most dangerous thing an agency owner can do is take a playbook from the wrong stage. Hiring a CRO at Stage 1 is suicide (no, you need hustle, not management). Hustling at Stage 3 is negligence (you need process, not heroics). Growth is not the addition of more numbers to the top line. It’s about identifying what game you are playing and having the discipline to alter the rules when that game stops playing.
Heather McLeod’s Practical Leadership Lens on Growth and Impact
Executive: Heather McLeodCompany: BNI GlobalIndustry: Referral networking organization (franchise model)Company Snapshot: A global membership organization built around structured, relationship-driven referralsFormat: CMO Journeys Interview Why It Matters Heather McLeod built her career in franchising by staying close to the people who run the business in the real world. Now she brings that same mindset to BNI, the world’s largest referral networking organization. Her journey is worth studying because she keeps marketing simple: find what drives revenue, then remove friction. For agencies, she’s unusually clear about what earns trust—and what gets ignored. Their Path, in Short After undergrad, McLeod struggled to land a marketing job in a saturated market. So she went back to school for an MBA. She later interviewed at The Dwyer Group (now Neighborly), a franchise home services organization, and said the fit felt right because she loved the people she met. That “people first” instinct became a pattern. “I’m a big believer that iron sharpens iron,” she said, explaining that she seeks leaders who make her stronger. Her first role in that world was as marketing manager for Rainbow International, a water, fire, mold, and smoke restoration business. She said she knew nothing about the category, so she immersed herself—spending time with franchise owners and letting them teach her what they needed and what would “move the needle.” She later moved to Mr. Rooter and worked for Mary Thompson, who would later become CEO of BNI. McLeod pointed out how relationships compound: the people you learn from early can reappear later, in bigger roles, when the stakes are higher. Over time, her definition of marketing expanded. She said she thinks broadly about what belongs in the “marketing bucket,” always asking: what are the revenue drivers, and how do we maximize impact there? In franchising, she explained, marketing is a major lever. Another lever is locations—helping existing locations market more effectively and putting more dots on the map through franchise sales. That mindset expanded her scope beyond traditional marketing. Big Themes From the Conversation McLeod’s energy comes from operators. She said spending time with franchise owners and master franchisees motivates her to do great work on their behalf. She also respects how complex multi-location really is. In her world, there are different owners in every market, different contact information, and a constant need for localization—“everything has to be able to be localized,” she said. Finally, she keeps coming back to scale. Franchise budgets, she explained, aren’t built like corporate-owned budgets because the corporate office is collecting a percentage fee to provide support. That’s why she needs solutions that scale, and why she often prefers approaches where “tech is doing the work and not people man hours.” Watch CMO Journeys Interview How They Choose the Right Agency Partners When I asked McLeod what she looks for in an agency partner, she started with a practical advantage: shorten the ramp. She likes partners who have worked in the industry because it reduces how much she has to teach. She’s happy to educate on brand. She wants industry best practices coming from the agency side. But she quickly clarified that “industry experience” is really about multi-location understanding. It doesn’t have to be the exact same niche, she said. What matters is knowing how to localize at scale and solve for complexity without costs going “through the roof.” In her world, that often means tech-enabled solutions that don’t rely on endless manual hours. Then she talked about delivery. She values agencies that deliver on what they commit to, and she prefers “over-delivering and under-promising versus the opposite.” She also noted a common frustration: the sales process can set one expectation, and the shift to account management can feel different. And she cares about chemistry. She wants partners she trusts and enjoys working with. On getting noticed, she didn’t mince words: stop with the really long LinkedIn messages. The kind that makes you scroll. “I can’t stand it,” she said. The bigger issue is timing. Most of the time, she doesn’t want to talk until she’s actively solving a problem. She gave a concrete example from her own work: she needed a website tool that could help users translate and move across multiple languages because she supports many countries. So she started hunting, checked what G2 said, researched options, and then booked calls. That’s why cold outreach usually doesn’t work on her. The exception, she said, can be face-to-face at events. And referrals matter. She leans on peers to ask, “Have you used a great agency in this space?” She uses those recommendations to validate options and shortcut decisions. She told one story that captured it. She worked with a social agency out of New York to help her show up more on LinkedIn. She wanted to post more, but she didn’t feel like anyone cared what she had to say. The agency helped her “get my feet under me” and find her voice. Later, someone at BNI noticed her LinkedIn and asked how to do something similar. When McLeod reached out, the agency founder replied with a twist: he was already in a BNI chapter in New York. McLeod loved that because he “got it.” What Stood Out McLeod is warm about the people she serves and blunt about what wastes time. One line captured her compass: “I want people who I can trust. I want people who I know are going to deliver on the things that they say.” It’s simple, human, and consistent with everything else she described. 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 Next Big Win Pro member.
The Best Time to Reach a CMO Is When Nobody Else Is Paying Attention
The Signal A new Chief Marketing Officer just joined a company you’ve never heard of. Maybe 500 employees, maybe 2,000. The LinkedIn announcement gets 47 likes. No press release. While everyone’s watching the splashy hire at Nike, you just scrolled past one of the strongest new business signals in your feed. Why It Matters Here’s what most people miss: there are 20-40 new CMO appointments every week at companies with 200+ employees. Not the big names, but mid-market companies actually building marketing departments, launching rebrands, replacing websites, and hiring agencies to do it. At major companies, 22% of marketing leaders have been in their role for one year or less. And 74% of marketing chiefs are first-time CMOs. These leaders are coming in with something to prove. They need quick wins. They’re assessing everything, including agency relationships, in their first 100 days. Research shows agency reviews typically happen six to nine months in as they “mark the start of a new era.” This isn’t just happening at companies everyone’s watching. It’s happening constantly in the middle market, where budgets are real but competition for attention is lower. The Mistake Most Teams Make They chase logos. When a new CMO lands at a brand they recognize, everyone piles on with the same message: “Congrats on the new role! We’d love to show you what we do.” Meanwhile, 30 other CMOs started the same week at companies you didn’t notice. The mistake isn’t just ignoring these opportunities. It’s not having a system to see them. Most teams rely on personal networks, referrals, and inbound. They’re not systematically tracking leadership changes because they don’t think of it as a signal. The Smarter Move Treat CMO moves at mid-market companies as a tier-one signal. This signal is different because it predicts action. You’re not interrupting business as usual. You’re entering during a natural assessment window. Reaching out in months 2-3 means you’re part of the evaluation, not fighting an incumbent. You’re there while they’re forming opinions, not after they’ve committed budget. But you need context, not just a name. When you know where they came from, what the company does, and what they’ve said publicly about their priorities, you can reach out with relevance. Not: “Congrats on the new role!” But: “I saw in your recent interview you mentioned building performance marketing infrastructure in mid-market B2B. We’ve worked with three companies in similar positions. Would it be useful to share what we’re seeing?” How to Operationalize It Track the signal systematically. Monitor CMO appointments at companies matching your ICP weekly, not randomly. There are tools built specifically for this. Platforms like NextBigWin Pro track executive moves at scale and filter by company size, industry, and role, so you’re not manually hunting LinkedIn every week. Layer in additional signals, such as a CMO move, funding, plus job postings, and it is a pattern, not a coincidence. Build context before you reach out. Spend time understanding their background, recent interviews, and what they’re inheriting. Time it intentionally. Not week one when they’re drinking from a firehose. Months 2-3 are the window. They’ve oriented, they’re assessing, and they haven’t locked in their roster. Offer perspective, not pitches. Share what other CMOs prioritized, mistakes you’ve seen, questions worth asking. While others chase announcements, there’s a massive middle market full of companies making real marketing investments, hiring leaders who need to prove themselves, and operating without entrenched agency relationships. They move faster, have fewer stakeholders, and are more willing to try something new.
How Chris Moloney Learned to Speak Creativity and Finance
Executive: Chris Moloney, Chief Marketing Officer and Chief Digital Officer Company: Cordell & Cordell Industry: Legal services (family law, expanding into estate planning) Company Snapshot: A nationwide family law firm focused on divorce, custody, and family law matters, expanding into estate planning while modernizing how marketing and client experience work together. Format: CMO Journeys Interview In This Article Why It Matters Their Path, in Short Big Themes From the Conversation How They Choose the Right Agency Partners What Stood Out The Inside Scoop Why It Matters Chris Moloney didn’t grow up dreaming about legal marketing. He grew into it—one chapter at a time—by following a simple obsession: clearer communication. Today he leads marketing and digital experience at Cordell & Cordell, where the work is high-stakes and deeply human. His story matters because he’s lived on both sides of the table: creative, marketer, and even CEO. And for agencies, his viewpoint is a practical guide to what actually earns attention—and what gets ignored. Their Path, in Short Chris traces his marketing origin story to a surprisingly specific moment: his parents bought him a Mac in high school. He didn’t just use it. He fell for it. The design tools pulled him into graphic arts, and graphic arts pulled him into a bigger idea—how visuals and words can educate people and open their eyes. Here’s the twist: in college, he was pre-law. He laughs about the irony now—working in a law office without being a lawyer. But that early interest still fits. His career has always been about helping people understand complicated things. He started as a creative. He worked as a creative director and a creative writer. He was “totally embedded” in the agency world. Then he moved into database marketing and digital marketing. Over time, he became the kind of leader who can talk about brand storytelling and spreadsheets in the same breath—and mean both. Along the way, he bounced between worlds that marketers often treat like opposites: big companies with deep resources and smaller companies that move fast. In his view, the best marketers learn both languages. They understand how slow systems think—and they keep their agile instincts alive. One of his biggest leaps came when he left a massive company to become the CEO of a tech firm that specialized in digital marketing and social media. The move shocked his system. But it taught him something he still carries: when you own the whole business, you don’t get to protect your budget just because you believe in it. You have to balance it. At one point, he even had to cut marketing spend—painful, he says, because marketing used to be the thing he defended most. That experience gave him a rare gift: empathy for the CFO and CEO mindset, not just the CMO’s. He also points to a lesson from his time leading marketing at Scottrade: the most powerful ally in marketing isn’t always the loudest person in the room. Sometimes it’s the CFO. When Chris could show measurable returns—using tools like Google Analytics and Google AdWords—his budget stopped being a fight and became a function. In his words, the question shifted to: How many new customers did you acquire, and what did it cost? That’s when marketing moved from “expense” to “engine.” Big Themes From the Conversation Chris keeps coming back to one idea: marketing is education. In legal services, he says, the industry is “filled with a lot of jargon” that confuses the average person. So the opportunity isn’t just to sell. It’s to make people feel more comfortable about whatever legal matter they’re facing. He also thinks deeply about speed—but not the reckless kind. He’s worked in regulated industries where moving too fast can create real risk. So his approach is to stay educated on what’s coming (especially in digital technology and AI), then apply it in low-risk areas first. He calls it being a “fast follower,” not a reckless pioneer. Another theme: respect the human. Chris has worked in industries where phone conversations built the entire category—finance, mortgage, legal. In those spaces, he doesn’t believe humans will vanish. People still want a person. They want reassurance. They want a real conversation. Which leads to one of his strongest beliefs: the digital experience should enhance human-to-human connection, not replace it. And then there’s his view of leadership through translation. He has lived the creative life and the finance reality. He’s been the one asking for budget—and the one cutting it. So he speaks like someone who has crossed a bridge and kept the map. His advice to marketers is blunt: learn how finance thinks. Learn what the CFO’s spreadsheets measure. Help them hit their goals. That’s how you stop being “the marketing person” and start being a business leader. Watch CMO Journeys Interview How They Choose the Right Agency Partners When I asked Chris how he finds agency partners, he didn’t start with a directory. He started with people. He leans on CMO groups and networks where marketing leaders trade notes. He also mentions organizations connected to Gartner, Forbes, and The Wall Street Journal, and he makes time for events where he can hear what other CMOs are working through. He’s picked up some of his best ideas there. For him, events aren’t just networking. They’re a live feed of what’s changing—and what’s actually working. But Chris is also clear: agencies can get on his radar directly. The catch is how they show up. He gets a lot of outreach. Too much, honestly. And most of it doesn’t work—especially the kind that swaps in his name and title, or references something shallow like a press mention. That’s not homework. That’s mail merge. What works is personalized effort that proves a real point. He says the most compelling outreach is when an agency takes its “strongest suit”—its “superpower”—and shows a small taste of it applied to his business. Not a full strategy deck. Not a giant pitch. Just enough to demonstrate thinking, craft, and relevance.
Why Agency–Client Performance Appraisals Are Now a Business Development Imperative
For years, agency–client relationship reviews were treated as something you did after things went wrong: a precursor to an RFP, a response to friction, or a defensive exercise once revenue was already at risk. That framing is no longer just outdated. It’s commercially reckless. In today’s market—where budgets are scrutinized line by line, procurement is deeply embedded, and clients expect measurable impact—waiting for a problem before evaluating performance is a failure of leadership. Agency–client performance appraisals must be treated as a core management discipline, not a damage-control tactic. Agencies that embrace this shift aren’t just retaining more clients. They are fundamentally changing how they are perceived: from interchangeable suppliers to accountable, strategic partners. As Denis Budnieski, former Verizon executive and PwC agency consultant, puts it: “A 360-degree review of the relationship is not a nice-to-have; it’s a must-have.” The data—and the market—back him up. “Assumptions” Are the Termites of Relationships. One of the most dangerous assumptions agency leaders make is that silence equals satisfaction. It doesn’t. In reality, many agency–client relationships don’t fail loudly. They decay quietly: Expectations drift but are never explicitly reset Perceived value erodes while scope remains unchanged Frustrations build across teams but never reach senior leadership Performance is discussed tactically, not relationally By the time these issues surface as declining revenue, reduced scope, or a surprise RFP, the outcome is often already decided. According to an ANA 2024 case study: “Brands that adopted formal evaluations saw an improvement in agency retention and project turnaround time by up to 35% in just one year.” That is not a “soft” cultural benefit. It is a measurable operational and financial advantage created by structure, transparency, and disciplined relationship management. Agencies that rely on intuition instead of evidence are effectively choosing to find out where they stand when it’s too late to change the outcome. What Makes an Appraisal Valuable—and What Makes It a Waste of Time Not all agency–client evaluations are useful. In fact, poorly designed appraisals can do more harm than good—reinforcing bias, triggering defensiveness, or generating feedback so generic it’s unusable. The appraisals that actually drive performance share three defining characteristics. They Are Data-Driven, Not Opinion-Driven High-value appraisals integrate both quantitative and qualitative inputs, including: Structured surveys across both organizations Role-based scoring (leadership, day-to-day teams, cross-functional partners) Thematic analysis of interviews Trend analysis over time This shifts the conversation away from personalities and anecdotes toward evidence. Data doesn’t eliminate hard conversations—but it makes them unavoidable and productive. They Deliver Value to Both Sides Many reviews are still framed as a one-way evaluation: the client grades the agency. That approach limits insight and undermines trust. The most effective appraisals are intentionally bi-directional, addressing questions such as: How is the agency performing against expectations? How effective is the client as a partner? Where do process breakdowns actually occur? Which behaviors on both sides enable—or block—success? When agencies are willing to be evaluated alongside their clients, defensiveness drops, credibility increases, and the discussion shifts from blame to improvement. That shift alone can change the trajectory of a relationship. They Are Conducted Consistently One-off reviews generate insight. Consistent reviews generate performance. Annual—or biannual—appraisals allow agencies and clients to: Track progress against prior benchmarks Validate whether changes actually worked Identify early warning signs before revenue is at risk Institutionalize “ways of working” that scale across accounts Consistency turns evaluation from an event into a management system—and systems, not intentions, drive results. Why This Is Now a Business Development Advantage For agency leaders focused on growth, disciplined performance appraisals are not just a retention tool. They are a competitive weapon. Agencies that run rigorous, data-driven appraisals are better positioned to: Expand scope based on demonstrated value Defend fees with evidence, not anecdotes Onboard new client stakeholders faster Reduce exposure to surprise reviews and competitive pitches Differentiate credibly in new-business conversations Increasingly, leading agencies are using appraisal outputs directly in business development: as proof points in credentials decks, as evidence of operational maturity, and as tangible demonstrations of partnership effectiveness. In a market where nearly every agency claims to be “strategic,” measured relationship performance is one of the few ways to prove it. The Bottom Line Agency–client relationships are among the most valuable—and fragile—assets an agency has. Yet many firms still manage them informally, intuitively, or reactively. That approach no longer works. A disciplined, data-driven, 360-degree performance appraisal—conducted consistently and designed to deliver value to both agency and client—is no longer optional. It is a leadership responsibility and a growth lever. Agencies that act on this insight won’t just protect revenue. They will build stronger partnerships, earn deeper trust, and create a durable advantage in an increasingly unforgiving market
Chris Foley Pilsner’s Journey From Agency Life to University Leadership
Executive: Chris Foley Pilsner, Chief Marketing & Communications Officer Company: Oakland University Industry: Public research university; higher education Company Snapshot: Mid-sized public research institution serving roughly 16,000 students with a strong regional, experiential focus. Format: CMO Journeys Interview In This Article Why It Matters Their Path, in Short Big Themes From the Conversation How They Choose the Right Agency Partners What Stood Out The Inside Scoop Why It Matters Chris Foley Pilsner is Oakland University’s first Chief Marketing and Communications Officer, and her path to the role runs straight through the agency world. She grew up inside creativity and client service, then moved into higher education, where the stakes are families, futures, and entire communities. Her story shows how classic agency training, data fluency, and a deep belief in education can work together. For agencies, she is both a former insider and a current buyer — someone who knows what great partnership feels like on both sides of the table. Their Path, in Short Chris grew up just outside Manhattan on Long Island, the daughter of two New York City public school educators. Education was always the family conversation. Her parents ended their careers as principals and superintendents, helping other leaders succeed. She knew she was not meant to be a classroom teacher, but the value of education was wired in early. At Villanova University, she studied English, women’s studies, and political science. She was drawn to the intersection of image and power — fascinated by moments like the Kennedy–Nixon debate and how perception shaped outcomes. She graduated during a recession, knowing only that she loved to write and loved figuring out how people tick. That curiosity led her into advertising, first as a secretary to a senior account person. Someone took a gamble on her, and that is how she “stumbled” into the industry. She became an account person at big agencies, working on consumer packaged goods, a bit of luxury, and pharmaceuticals. She learned how to sell products where you cannot always say the direct benefit, and she worked with multinational corporations. A transfer to London broadened her view of how business works and how to build disciplined client relationships — understanding the business situation, defining what needs to be done, and then delivering. Life moved her next to Ann Arbor, Michigan, where she joined a small regional agency just as social media was becoming mainstream. It was a different scale but another rich learning experience. A later move to Western Massachusetts shifted the picture again; there were few agencies there, and the region was rural. She began consulting and, through her husband’s connections at the University of Massachusetts, got a first look at higher education as a marketer. That consulting work became her on-ramp into a new industry. In higher ed, she discovered a world that felt both familiar and very different. Her agency training served her well, but she also saw how immature the sector could be in marketing and communications. She had to explain why marketing mattered and why people and budgets for it were not a luxury. At UMass’s Isenberg School of Management, she worked for a dean who deeply valued branding. With his support, she hired a marketing consultancy to run the school’s first brand study and brought in its first ad agency — critical inflection points that gave her data, not just anecdotes, about the brand. That experience led to a series of leadership roles in higher ed marketing and communications. Over time, she realized how much she enjoyed not just storytelling but also CRM, digital transformation, and data. Eventually, Oakland University asked her to become its first Chief Marketing and Communications Officer, charged with unifying brand, marketing, and communications for a regional public research university with big ambitions. Big Themes From the Conversation One theme that runs through Chris’s story is a love of what makes people tick. In agencies, she gravitated toward strategy and consumer insights, not just the flashy creative. She loved pairing classic CPG discipline with harder categories like spirits and pharma, where you must tell a story without saying everything outright. That same curiosity now applies to prospective students, parents, faculty, and alumni — understanding what they care about and how to talk to each of them clearly. Another theme is how deeply she believes in the power of education. Coming from a family of educators, she jokes that she was never going to be a teacher, but she never lost the sense that education is essential. She talks about learning to sell things the world may not truly need, like another toothpaste, and then contrasts that with education, which she sees as a partial solution to many of society’s problems. That belief gives her work in higher ed a mission-driven energy. Data is a third throughline. Early in higher ed, she realized they had almost no hard data about their brand — only stories and perceptions. So she brought in a firm to conduct a brand study and used that as a baseline. Later, working in CRM and digital transformation, she came to see data as “everything.” She laughs that if you had told her early in her career that she would geek out on spreadsheets and first-party data, she would have laughed. Looking back, she wishes she had taken that Excel course sooner. She also thinks about brand as the end-to-end experience, not just a tagline. In her view, higher ed asks people to make a huge, complex, multi-year decision. No two students will have the same experience, yet universities still have to boil it down into a short, clear idea and then build a journey around it. For Chris, that means mapping the customer journey, simplifying the story without flattening it, and recognizing that branding includes customer service, advising, and every interaction — because “the brand is the experience.” Finally, there is a quiet but firm commitment to sustainability and self-care. Chris loves her job and throws herself into it, but she is
Turning Executive Interviews Into New Business Signals
Most agencies want to be proactive with new business. In reality, that often means building a list of dream clients and starting outreach with very little context. You don’t know if a brand is in market, what they’re focused on, or whether anything is changing. Timing becomes a guessing game. When results stall, the default response is more volume: more emails, more calls, more follow-ups. The effort increases, but relevance doesn’t. That’s why traditional cold outreach feels inefficient and exhausting. There is a smarter way. It starts with using signals to guide your approach and then leading with value to build relationships over time. The Signal Brand-side marketers speak publicly more than most agencies realize. Interviews and profiles show up in places like Ad Age and Adweek. Podcasts like The CMO Podcast go deeper than most written articles. Leaders also surface real insight on webinars, panels, and in direct executive conversations, including NextBigWin’s CMO Journeys. These conversations aren’t just content. They are early signals of what leaders care about, what pressure they’re under, and what problems they’re trying to solve. Why It Matters These interviews happen without sales pressure. There’s no pitch and no vendor spin, so leaders often sound more honest and specific than they would in a sales meeting. When a marketing leader says they’re rethinking an approach, inheriting new expectations, or being asked to prove impact in new ways, that’s a signal that priorities are shifting. Those moments often show up months before an RFP or a formal agency search. This is early intelligence, not late-stage intent. The Mistake Most Teams Make Most agencies either ignore this content or misuse it. They either consume it passively and do nothing, or they pounce with a message that basically says, “I saw you say a thing, and we sell the thing.” That feels opportunistic, even if the timing is good. Signals should guide your outreach. They should not turn you into a faster cold emailer. The Smarter Move The goal isn’t to quote the interview. It’s to use it to understand what the marketer is navigating and then show up with value. AI makes this easier. You can pull transcripts from interviews and webinars, then scan for language that signals change, pressure, or uncertainty. AI doesn’t replace judgment, but it helps you find the few lines that matter without listening to 45 minutes end-to-end. Once you spot a useful signal, your next step is simple: ask, “What value can we offer that matches what they care about?” That value could be: original research you’ve already done (or can quickly pull together) a relevant case study with real outcomes a point of view or short checklist that helps them think an invite to an executive roundtable on the exact theme they raised a reason to connect at an event you both may attend What Good Outreach Looks Like Bad outreach (cringe) sounds like: “I saw your interview about attribution. We do attribution. Want to talk?” Good outreach sounds like: “I caught your point about attribution being harder with today’s channel mix. We recently pulled a short set of lessons from similar brands on what’s working and what isn’t. Happy to send it over either way. I appreciated how clearly you explained the challenge.” Notice the difference: one is a pitch. The other is help. How to Use This Track where your target accounts show up publicly. Save transcripts, not just links. Look for repeat themes across multiple leaders. If you keep hearing the same challenge, consider hosting a small Executive Roundtable and inviting a few of the people talking about it. Across ongoing executive conversations, including NextBigWin’s CMO Journeys, one pattern consistently emerges: the teams that win don’t “time the market” by increasing outreach volume. They build genuine relationships before the buying window opens, so when it does, they’re not a stranger. That’s how you trade volume for relevance and traditional cold outreach for smarter timing and better relationships.
The Mindset Shift That Shaped Justin Steinman’s CMO Style
Executive: Justin Steinman, Chief Marketing Officer Company: ModMed Industry: Healthcare SaaS; specialty EHR, practice management Company Snapshot: PE-backed, fast-growing platform serving 40,000+ specialty providers across 15+ specialties. Format: CMO Journeys Interview In This Article Why It Matters Their Path, in Short Big Themes From the Conversation How They Choose the Right Agency Partners What Stood Out The Inside Scoop Why It Matters Justin Steinman is the Chief Marketing Officer of ModMed, a specialty-focused healthcare SaaS company that supports tens of thousands of providers with EHR, practice management, revenue cycle, patient engagement, and AI-driven tools. He has spent much of his career moving between healthcare, data platforms, and software, often wearing both the CMO and GM hat at the same time. That mix gives him a rare view of how story, numbers, and operations all fit together. For agencies, his journey is a masterclass in what a modern, operator-minded CMO looks for in partners—and how he actually makes those decisions. Their Path, in Short Justin didn’t start in marketing or healthcare. He started as an English and history major who fell in love with storytelling at a college newspaper. Running The Daily Dartmouth, he learned to write on deadline, accept edits from tough editors, and motivate dozens of unpaid student volunteers to ship a paper five days a week. That’s where he first learned how to lead, empower, and hold a high bar for quality without crushing people in the process. After business school, he joined Novell and stepped into the world of enterprise technology. Over time, he gravitated toward healthcare and healthcare IT and stayed there. He talks about himself as a storyteller who wants to understand people’s challenges and then figure out how the company he works for can help improve their quality of life—not just their efficiency or revenue. People buy from people, he says, and stories that speak to emotional needs beat “corporate gobbledygook” every time. At Definitive Healthcare, he sat on top of a massive healthcare data set and launched a podcast, “definitively speaking.” Each episode used real data as a jumping-off point for conversations with industry leaders. The show wasn’t a product pitch. For him, success was simple: if someone walked away thinking the podcast was interesting and connected Definitive Healthcare with data in their mind, the job was done. He has also led as both a GM and a CMO, owning P&L while running brand and demand. That experience shaped how he thinks about marketing as a lever for growth and how he talks to other operators about pipeline, bookings, and awareness in ways they actually understand. Along the way, he’s led high-stakes moments such as a full company rebrand at Insora Health, where the business changed its name from Therapy Brands. For those “once in a company’s life” moves, he’s turned to agencies with deep repetition and expertise. Today, as CMO of ModMed, he’s energized by two things: a culture he describes as full of decent people with low ego, and a product he genuinely believes in. He points to an AI product demo he ran live, unscripted, for fifteen minutes on stage in front of 1,200 customers. It worked so well that ModMed put that unedited demo video on the front page of its website. For someone who admits he has “sold some vaporware” earlier in his software career, that kind of reality is a big deal. Big Themes From the Conversation One theme that comes up again and again with Justin is storytelling. He calls himself a storyteller and says he’s always been drawn to learning about people and sharing what he learns. In his view, each person is “the collection of their stories,” and the same is true for brands. He believes that if you can connect with a buyer on a human level, you can cut through the buzzwords that usually clog B2B marketing. Another theme is craft—especially the craft of writing. He talks about getting rewritten early in his newspaper days by people who now write for places like The New York Times and The Wall Street Journal. That experience taught him how to write and how to take feedback. It also taught him how to enforce quality while still appreciating people’s effort. Those lessons show up in how he leads teams under pressure now. Justin also sees marketing as a customer-service business. His “customers” are not just buyers and physicians; they’re internal teams too: product management, sales, sales engineering, HR, finance, even investors. Having lived in a GM seat, he understands the pressure of “trying to hit my number and using marketing as a lever.” That’s why he pushes his team to translate complex marketing activity into simple, operator-friendly metrics like pipeline coverage, SQLs, bookings, and clear brand health numbers such as awareness and consideration. Scale is another recurring idea. Justin thinks in systems. He talks about building a marketing organization where everyone in the company has a single point of contact into “the marketing machine.” He organizes around core functions like product marketing, marketing operations, demand generation, corporate marketing, and partner marketing. Then he connects those to ModMed’s own structure—product teams on one side, specialties and sales segments on the other—so that planning becomes one integrated story, not a set of disconnected campaigns. That story, for ModMed, is the “AI powered practice.” It’s a single idea that can flex. A dermatology marketer can talk about building an AI-powered dermatology practice. A product marketer can talk about building an AI-powered practice with specific tools like the EMR or an AI ambient solution. Justin’s line is simple: if you stand for everything, you stand for nothing. One master story, with smart customization, is how he keeps the company focused. Finally, his leadership philosophy is grounded in bringing people along. He shares advice from an early mentor: it can be better to get 80% of the way to your destination with 100% of the people on board than to arrive alone. He’s honest that he used to be
What Do We Do Next? Your Rapid-Response Guide to Your Agency’s Next Client Contract Negotiation
New business feels like a game of “hurry up and wait” for agencies. Until you’ve landed the client or the account—when it’s all hurry, no wait. Your team is excited to start work, and your accountant is eager to see revenue. All as soon as possible. What nobody wants? A drawn-out contract negotiation that slows down progress. So, in the spirit of closing agreements promptly, without sacrificing your agency’s leverage in the process, here are some suggested “rapid responses” to a few of the common deal points most agencies encounter frequently in new business. The Challenge: Payment Terms That Aren’t Reasonable for Your Agency Agencies are generally protective of their payment terms in client contracts. The challenge usually arises when you are onboarding a new client whose payment policies don’t align with the agency’s needs. One part of the problem is lengthy pay terms. The other, less-noticed part of the problem is contingencies that can draw a payment term out even longer than it looks on its face—terms like invoice approval rights, charge dispute provisions, or unreasonable pass-through cost reimbursement rules. Your Agency’s Rapid Response: Long payment terms are a business problem, not necessarily a legal issue. Know your agency’s benchmarks and its capacity to financially tolerate payment terms that don’t accommodate your overhead cycles and profitability targets. Beyond that, consider some of the following responses: Ensure that the payment term clock begins to run on the date of invoicing. Not on the date of “approval” of the invoice. Require that any objections or errors in agency billing be raised promptly by the client, or waived if not prompt. Bill in advance for all third-party expenses, such as media or production. If you bill in arrears for agency services, consider “split billing” for expenses vs. agency services—one invoice for expenses, one for services, on different remittance schedules. The Challenge: Standard “Work for Hire” IP Language and Restricted Portfolio Rights Most client-provided services contracts will address IP rights in agency work with a broad brush—the agency creates, the client owns. Many brands now also default to prohibiting the agency from displaying samples of the work it creates for them. Sometimes the restriction covers even mentioning the brand as a client. Imagine the impact this has on your ability to attract new clients in the future. These IP defaults and work display restrictions have real-world consequences for your agency’s revenues and future business development efforts. And there may be some work that the agency doesn’t intend to transfer to the client (like your proprietary knowledge, software, methodologies, etc.), or cannot transfer to the client (like third-party licensed assets or anything generated by AI). Your Agency’s Rapid Response: Address this deal point with these recommended responses: Include terms that the rights to work your agency agrees the client will own do not transfer until the agency is paid in full. Carve out rights transfers in any work that is proprietary to the agency (this gets licensed, not transferred), or work that is third-party created (like stock assets). Reserve a license for the agency to display portions of the work that are not confidential for its promotional and marketing purposes—including the right to share the client’s brand name. If you’re unable to secure this term, negotiate instead for a “disclose/display with permission” term to share this information in your agency’s marketing. This is a midpoint on the issue that at least keeps the door open to the possibilities for promotional use cases later. The Challenge: Exclusivity Demands by The Brand One outcome of agency specialization and niching is that clients have increased their expectations about restricting your agency’s ability to serve other similar businesses or product categories. Brands want to guard against their agencies working for perceived competitors. But your agency needs flexibility to pursue these other opportunities, or an economic incentive to agree to exclusivity. Your Agency’s Rapid Response: If you’ve made the decision that your agency will accept some exclusivity requests in order to serve the client, consider these response options: Request, and expect, minimum spend requirements and/or premium pricing from the client. Choose your language as carefully as you like; however, the agency deserves a premium for foregoing other business opportunities to serve the client. Suggest limitation of the exclusion to a narrowly defined list of competitors. Suggest limitation of the exclusion to as short a list as possible of product or service categories. Request that the exclusivity end as soon as the agency’s services to the client do, not for any “tail” period after they conclude. The Challenge: AI Compliance and Responsibility Expectations Increasingly, agency-client agreements are addressing the responsibility of agencies when using AI. This is particularly true in the case of the agency using GAI to create deliverables, but is also an increasingly recurrent challenge when it comes to data privacy compliance and confidentiality. This is a balancing act during your contract negotiations. AI’s presence in the work stream is dynamic, and the law around the legal issues it can create is still unsettled in many areas. Meanwhile, the agency wants to display proactivity in AI adoption, and the client has risk management concerns and likely has more conservative organization policies around AI use. Your Agency’s Rapid Response: The client will expect your agency to share some of the risk when using AI to create and deliver work. Your role in the negotiation process is to balance the risk as fairly as possible, given the legal unknowns. Here are the starting points for responding: Require the client to acknowledge the agency’s use of AI in writing. Include the acknowledgment in the contract. Include approval and legal review of all deliverables by the client as a defined client responsibility. Require the client to disclose its AI use policies to the agency before work is performed. Expect the agency to have to assume some part of the responsibility if any of the work it creates (using generative AI, especially) infringes someone’s intellectual property or data privacy
The Generalist Trap: Why Saying Yes to Everyone is Sinking Your Agency
Let me guess: You started your agency by saying yes to everyone. The local lawyer. The fitness coach. That friend-of-a-friend with a “cool app idea.” It felt like momentum. Like you were building something. But here’s the thing: That “something” was a trap. Let’s call it what it is: the Generalist Trap. You know the symptoms: Context-switching chaos. Employees pleading with you not to sell another deal. A team stretched thin, relearning new industries every week. You—the founder—becoming the bottleneck, the only one who “gets” every client. Work that’s good, not great. And clients who leave because they don’t see the difference between you and the next agency on Google. Sound familiar? You’re not alone. Most agency founders fall into this trap early on. And it makes sense: generalists survive. They hustle. They scrape by. But they don’t scale. The Generalist Trap is a Cycle—And It Feeds Itself Here’s what most agency owners miss: each “yes” sets off a chain reaction that circles right back to more “yeses.” It’s not just inefficient—it’s a loop. And if you don’t break it, it’ll run your agency into the ground. Let’s walk through the cycle: 1. It starts with “Yes to Everyone.” That random inbound lead? You take it. That one-off project in a new niche? Why not. But this isn’t building a business—it’s building a time bomb. 2. Next comes Context Switching. Now you’re building a funnel for a SaaS startup on Monday, running local SEO for a dentist on Tuesday, and launching a paid media campaign for a nonprofit on Wednesday. No momentum. No rhythm. Just whiplash. 3. Which leads to Operational Inefficiencies. No repeatable systems. No SOPs. No leverage. Your team spends more time learning than executing. Your margins vanish. 4. Then the Founder Becomes the Bottleneck. You know every client’s backstory because you sold them. So you become QA, strategist, firefighter. Growth stalls because nothing scales without you. 5. You Become a Commodity. Generic agencies get generic results. You’re not known for solving a specific problem, so you blend into the crowd—and clients start shopping on price. 6. Client Churn Kicks In. Without deep expertise, your results are average. Clients leave. Retainers die. And your team starts wondering if this is really worth it. 7. You Chase Revenue. Churn hurts. Cashflow gets tight. So you do what you’ve always done: you say yes to anyone. And the whole thing starts again. And that’s the trap. A hamster wheel disguised as hustle. Here’s the visual to drive it home: You Can’t Grow What You Can’t Systemize This isn’t just a list of problems—it’s a feedback loop. The longer you stay in it, the more it costs you: in time, in energy, in sanity. And the only way out is to specialize in a vertical market. Vertical specialization gives you: Clear positioning Tighter processes A more empowered team Higher margins Clients who stick around And a business that doesn’t rely on you doing everything Want Out of the Cycle? The first step to breaking free from the Generalist Trap is getting clear on where you are today—and what’s holding you back. That’s why I built a quick, powerful assessment to help agency founders like you spot the hidden gaps in your positioning, marketing, and sales systems. In just a few minutes, you’ll get a personalized snapshot of where you stand—and your best next moves to scale with less chaos and more momentum. Take the free Agency Growth Scalability Assessment here → https://geni.us/eY3xB Let’s stop the cycle—and start building the agency you actually want.