Glenn Gow, The Scaling Executive Coach and host of The Scaling Executive Podcast, sits down with Cleveland Brown, CEO and Co-Founder of Payscout, a global payment processing provider operating across six continents. Payscout earned three consecutive appearances on the Inc. 500/5000 list, ranking as high as number 383 overall and number 24 within financial services. Cleveland launched the company in 2011 and has scaled it through international expansion, multiple acquisitions, and innovative spin-offs including CyberDyme, which pioneered the first virtual reality payment for a physical good.
This conversation covers how Cleveland built a culture precise enough to guide decisions at every level without his involvement, why AI adoption must follow a specific layered sequence to produce real business value, and how a vision stated clearly enough allows teams to bring the CEO ideas he never would have found on his own.
This episode is for CEOs navigating acquisitions, international expansion, or rapid headcount growth who want a concrete framework for scaling culture rather than just products and systems.
Key Takeaways
- Cleveland Brown says the biggest scaling mistake he made early was having a clear plan for products and operations during an acquisition but no plan for integrating culture, which slowed the entire integration down.
- Brown’s culture framework at Payscout consists of four defined attributes, each with team-authored definitions built from cross-functional input, giving every employee the same behavioral reference point regardless of role or location.
- Glenn Gow observes that Cleveland is the only CEO he has worked with who can recite the company’s cultural values from memory without hesitation, which he identifies as the clearest signal that a culture is actually living inside an organization rather than sitting on a slide deck.
- Cleveland Brown argues that the CEO’s primary job is not to make decisions but to create the environment and framework within which good decisions get made at every level of the organization.
- Brown’s layered AI adoption model moves from infrastructure understanding to application selection to data organization, in that order, and he warns that jumping directly to prompting tools without completing the first two layers produces outputs with no grounding in the company’s actual context.
Culture That Cannot Be Recited Cannot Be Scaled
Cleveland Brown learned the importance of culture-first integration the hard way. The first company Payscout acquired came with its own established identity, its own ways of working, and its own internal norms. Payscout had detailed plans for product integration and operational efficiency. It had no plan for integrating culture.
“We had a very clear plan in terms of products, efficiency mechanisms, both operationally and from a product perspective. Those things are more or less the paperwork that you do, but you have to look at scaling people.”
The result was friction that slowed the integration at every level. When the acquired team did not share a common understanding of how to behave, how to make decisions, or what mattered, the gap between the two organizations did not close on its own. Cleveland’s conclusion was direct: culture integration must lead, not follow, the operational integration.
“What I learned is that you need to lead with the culture. Make sure that there’s a firm understanding of the culture that the company that you’re acquiring is going to integrate into so that really on day one of acquisition, you’re up and running.”
The Payscout culture framework Cleveland built in response has four components: vision, mission, cultural attributes, and the behavioral definitions that govern each attribute. The attributes themselves, which include integrity, trust, reliability, fun, best idea wins, feedback welcome, customer happiness, and always learning, were not written by Cleveland or taken from a dictionary. They were built by the team.
“The definitions were built by our team. These were cross-cultural definitions across different aspects of our business. We basically had everyone create a definition. We looked at the common denominator of everyone’s definition and put that together.”
The reasoning behind team-authored definitions is precise: at any meaningful scale, individuals will internalize the same word differently. If “feedback welcome” means something different to five people, it means something different to five hundred. The act of building shared definitions collapses that variance before it becomes a behavioral inconsistency.
Once defined, Payscout puts each attribute through a four-step model: memorize, internalize, articulate, and teach. The outcome is a culture that travels with the organization rather than staying in the founder’s head.
Glenn Gow tested Cleveland on this in real time and found something he described as genuinely rare: Cleveland recited all eight cultural attributes without pause or reference to notes. Glenn’s observation was pointed.
“You’re the only CEO that’s been able to rattle off what are our corporate values without thinking. Most of them go, well, let me go look them up. Which means they’re not real. They’re not living.”
The CEO’s Job Is to Build a Decision-Making Environment, Not to Be the Decision Maker
The most direct expression of what Cleveland’s culture framework is designed to produce is his framing of the CEO role itself. He does not define the job as setting strategy, managing people, or driving revenue. He defines it as creating the environment in which decisions get made well, by anyone in the organization, at any moment.
“As a CEO, my job is to create an environment for decision making.”
The framework Cleveland uses for decision making has three layers. The first is experience: what do we already know that applies here? The second is research: if experience is insufficient, what can we learn that fills the gap? The third is culture: can we wrap the cultural attributes around the path we are choosing and explain why that path reflects who we are?
“As you look at your experience and research, we support decisions if you can wrap the culture into why you chose a certain path. And we live with the result. We embrace the result. We don’t care what the result is. We just know that you took a three-dimensional approach to that decision and we support it at Payscout.”
The significance of this framework for a scaling organization is substantial. Most companies hit decision bottlenecks as they grow because the people with the authority to decide are not always available and the people closest to the problem do not feel empowered to act. Cleveland’s three-layer model resolves that bottleneck. Any team member who can point to their experience, their research, and their cultural reasoning has the standing to make a decision and be supported in it.
A Vision Stated Clearly Enough Allows the Team to Bring Ideas the CEO Never Had
Payscout’s expansion into virtual reality commerce through CyberDyme did not begin with Cleveland. It began with his COO and colleagues from Film Antics, who recognized a connection between storytelling-driven media and the future of payments inside spatial computing and brought it to him.
Cleveland’s response to that story is not credit-taking. It is an observation about what made that moment possible.
“If they didn’t have the platform in which to approach the organization, approach me, partnership, leadership, management, and say, hey, take a look at this, we would have never have accomplished being the first company in the world to execute a payment in virtual reality for a good.”
The vision that created that platform is specific: to be the thought-leading and fastest-growing global payment processing provider in the world. The word “thought-leading” is load-bearing. It signals to the team that bringing forward an idea about the future of payments is exactly the kind of contribution the vision rewards.
Glenn Gow identified this as a distinctive leadership quality: Cleveland is not the CEO who requires all ideas to originate with him. He is the CEO who creates the conditions for ideas to surface from anywhere in the organization, because the vision is clear enough that people can evaluate whether an idea fits before they bring it forward.
AI Adoption Without the Right Foundation Produces Outputs With No Grounding
Cleveland Brown’s philosophy on AI adoption is structured as a three-layer sequence, and he is explicit that executing the layers out of order produces limited value at best and misleading outputs at worst.
The first layer is infrastructure. Before applying AI to anything in the business, Cleveland argues that leaders must understand the landscape of available platforms, how they differ architecturally, and what each one is actually built to do.
“The first thing that people have to understand is what does the infrastructure and architecture of artificial intelligence look like? What’s the difference between Chat and Gemini and Copilot and Claude? You need to figure that out.”
The second layer is the application layer: once a leader understands what the infrastructure can do, the question becomes which applications map to the specific efficiency or growth problems of their particular business. This is not a generic answer. It is industry-specific and company-specific.
The third layer is data. An AI system that cannot access a company’s actual context, its culture attributes, its customer problems, its competitive landscape, will produce outputs that are generically plausible but organizationally useless.
“When you’re just throwing prompts at it — hey, build me a slick marketing PDF for my product — does it know the culture attributes? Does it know the problems of your consumers? Does it know your competition and the competitive models? There are so many things that you actually have to put in play to make those prompts work.”
The framework applies equally to internal efficiency and to product development. Payscout is working through both paths: using AI to make the organization more efficient, and integrating AI into payment products to help consumers operate more efficiently. Cleveland’s insistence on sequence, infrastructure before application before data, is his way of ensuring that the investment in AI produces grounded, company-specific value rather than generic outputs that could belong to any competitor.
What Cleveland Brown Builds and Applies at Payscout
| Principle | What it means in practice | Named evidence from this interview |
| Lead with culture in every acquisition | Operational integration plans without a culture integration plan create behavioral friction that slows everything else. Culture must be defined and communicated before day one of any acquisition, not after systems are merged. | Payscout’s first acquisition stalled on cultural misalignment despite having detailed operational and product integration plans; Cleveland rebuilt the process to lead with culture on every subsequent deal |
| Build culture definitions with the team, not for them | Attributes defined by leadership carry the leader’s interpretation. Attributes defined through cross-functional input, then distilled to a common denominator, carry a shared meaning that scales consistently across geographies and roles. | Payscout’s eight cultural attributes were built from definitions contributed by team members across the organization, not drafted by Cleveland or taken from a dictionary |
| Create a decision-making environment, not a decision-making dependency | A CEO who is the primary decision maker creates a bottleneck. A CEO who builds a three-layer decision framework, experience, research, culture, empowers every team member to decide and be supported in that decision. | Cleveland describes his job as creating the environment for decision making, not making decisions himself; Payscout supports any decision an employee can defend through the three-layer framework |
| State the vision precisely enough that the team can self-filter ideas | A vision specific enough to be directional allows team members to evaluate whether an idea fits before bringing it forward. That self-filtering produces better ideas and more of them. | Payscout’s COO and Film Antics colleagues identified the virtual reality commerce opportunity and brought it to Cleveland because the thought leadership vision gave them confidence the idea belonged at Payscout |
| Follow the AI adoption sequence: infrastructure, application, data, in that order | Jumping to AI application without understanding the infrastructure landscape or organizing company data produces generic outputs with no grounding in the business. The sequence matters as much as the tools. | Cleveland warns specifically against using AI prompting tools before completing the infrastructure and data layers, noting that outputs without company context are useless regardless of how sophisticated the prompt is |
Quotes from This Episode
- “As a CEO, my job is to create an environment for decision making. As you look at your experience and research, we support decisions if you can wrap the culture into why you chose a certain path. And we live with the result. We embrace the result. We don’t care what the result is. We just know that you took a three-dimensional approach to that decision and we support it at Payscout.” — Cleveland Brown, CEO and Co-Founder, Payscout
- “What I learned is that you need to lead with the culture. Make sure that there’s a firm understanding of the culture that the company that you’re acquiring is going to integrate into so that really on day one of acquisition, you’re up and running.” — Cleveland Brown, CEO and Co-Founder, Payscout
- “The definitions were built by our team. These were cross-cultural definitions across different aspects of our business. We basically had everyone create a definition. We looked at the common denominator of everyone’s definition and put that together.” — Cleveland Brown, CEO and Co-Founder, Payscout
- “If they didn’t have the platform in which to approach the organization, approach me, partnership, leadership, management, and say, hey, take a look at this, we would have never have accomplished being the first company in the world to execute a payment in virtual reality for a good.” — Cleveland Brown, CEO and Co-Founder, Payscout
- “When you’re just throwing prompts at it — hey, build me a slick marketing PDF for my product — does it know the culture attributes? Does it know the problems of your consumers? Does it know your competition and the competitive models? There are so many things that you actually have to put in play to make those prompts work.” — Cleveland Brown, CEO and Co-Founder, Payscout
Frequently Asked Questions
How do CEOs build a culture that holds together through acquisitions and international expansion?
Cleveland Brown argues that culture must lead every acquisition, not follow it. The operational and product integration plans that most companies prepare in detail are the easy part. The hard part is ensuring that the people joining through an acquisition share a clear, precise understanding of what behavioral norms mean inside the new organization. At Payscout, Cleveland solved this by building team-authored definitions for each cultural attribute, defined through cross-functional input and distilled to a shared common denominator, then putting those attributes through a four-step model of memorize, internalize, articulate, and teach. The result is a culture that travels with the organization at any scale because every team member holds the same behavioral reference point, regardless of where or how they joined the company.
How should a CEO think about their role in organizational decision making as a company scales?
Cleveland Brown defines the CEO role not as the primary decision maker but as the architect of the environment in which decisions get made well at every level. His three-layer decision framework, experience, research, and culture, gives every Payscout team member the tools to make a decision and defend it without requiring Cleveland’s involvement. Any decision that draws on relevant experience, closes gaps through research, and can be explained through Payscout’s cultural attributes is a decision the organization supports, regardless of outcome. This framework removes the decision-making bottleneck that typically forms around founders and CEOs as organizations scale.
What is the right sequence for adopting AI inside a scaling company?
Cleveland Brown argues that AI adoption must follow a three-layer sequence to produce grounded, company-specific value. The first layer is infrastructure: understanding what the major AI platforms are, how they differ architecturally, and what each is built to do. The second layer is application: identifying which tools map to the specific efficiency and growth problems of the business. The third layer is data: organizing internal company data so it can be fed into the AI systems being used, giving those systems the context they need to produce relevant outputs. Skipping to prompting tools before completing the infrastructure and data layers produces outputs that are generically plausible but have no grounding in the company’s culture, customers, or competitive position.
CEOs Work with Glenn Gow to Scale Their Companies by Scaling Themselves First
Glenn Gow is The Scaling Executive Coach — he coaches ambitious executives into the CEO seat and CEOs into successful exits. With 25 years as a CEO and 5 years in venture capital, Glenn helps leaders scale their companies by scaling themselves first. If this conversation was useful, you can apply for executive coaching with Glenn Gow or apply to be a guest on The Scaling Executive Podcast.
