The counterintuitive part was realizing that hiring someone doesn't mean you'll have less to do. It means you have to give away something you built. We went from 5 to 18 in about two years. Every time we added a leader, the person who owned that function before would say they were drowning and needed help. Then the new hire would arrive and suddenly they wanted to keep all their projects. I watched people fight to hold onto work they'd complained about for months. So I stopped looking for people who could "take things off my plate" and started looking for people who made me excited to hand over something I cared about. If I couldn't picture myself genuinely wanting them to own my best work, they weren't the right hire. That filter eliminated a lot of technically qualified candidates who would have created territorial battles instead of actual capacity.
One lesson I learned when growing the team was that technical skill alone doesn't guarantee someone will succeed in a startup environment. Hiring people who communicate clearly, take initiative, and fit well with the team often mattered more than just their experience on paper. This changed how we evaluate candidates. We prioritize adaptability alongside experience to ensure each new hire contributes effectively to the team's performance.
Stop Being the Hero When scaling a leadership team from 5 to 20+ people, the most counterintuitive lesson I learned was that my value as a leader was no longer found in having the right answers, but in having the right questions. At a team of five, a leader can still be the "hero" who steps in to solve every complex problem. However, at a team of twenty, that same hero-mentality becomes the single greatest bottleneck to growth. I realized that by providing the solutions, I was inadvertently creating a culture of dependency rather than a culture of empowerment. This insight shifted my approach to leadership and future hires. I moved from being a "reactive manager" to a "transformative coach" by implementing the GROW model. This framework allowed me to build the "Backbone" of accountability while maintaining the "Heart" required to build trust and psychological safety. How it Changed My Hiring Approach This shift changed what I look for in future hires. Instead of just searching for technical "experts" who could execute tasks, I began hiring for "coachability" and the ability to scale others. I started looking for leaders who understood the "Ripple Effect"—those who recognized that their primary job was to build a pipeline of leadership behind them. Now, when I hire, I prioritize candidates who demonstrate the Four Cs: Complex problem-solving, Connection, Creativity, and Coaching. This approach ensures that as the organization grows, our human connection scales alongside our technology, creating a resilient culture that can navigate the complex times ahead.
We learned an important lesson about growth and leadership timing. With five people, leadership forms naturally through daily work. With twenty people, leadership must be clearly designed. We hired quickly and assumed structure would appear on its own. That assumption proved wrong. Roles overlapped and decisions slowed. People felt unsure about ownership. Confusion increased as the team expanded. That experience reshaped how we hire today. We delay leadership hires until the same problems repeat consistently. We hire to solve real gaps, not imagined future needs. Interviews now focus on accountability and pattern thinking. We ask how candidates simplify chaos and make decisions clear. This approach reduced overlap and lowered stress. Teams understand who decides and why.
One counterintuitive lesson was that experience matters less than decision-making clarity once you scale. Early on, we prioritised seniority and impressive backgrounds. As the team grew, it became clear that leaders who could make clear, aligned decisions without constant reassurance outperformed more experienced hires who needed heavy context or validation. That insight changed our hiring approach. We now prioritise people who demonstrate strong judgment, ownership, and the ability to operate within defined frameworks. Titles and years matter less than how someone thinks when information is incomplete.
The biggest curveball I hit while scaling our leadership team was realizing that the "hero" who saves everyone's skin when you're a team of five usually becomes your biggest bottleneck once you hit twenty. In a tiny squad, you need leaders who aren't afraid to jump in the trenches and fix things themselves. But as you grow, that "doer" instinct actually backfires. It stops you from building the repeatable systems you need to actually scale. This realization totally changed how I interview people now. I've stopped looking for the person with the fastest hands-on execution. Instead, I'm looking for "system architects"--the kind of leaders who'd rather build a process than be the smartest person in the room. At Coders.dev, we've learned that scaling isn't really about just piling on more talent; it's about managing the mess of interactions that comes with growth. Now, we prioritize candidates who can show us how they've made themselves redundant in their past roles. If a leader can't prove they've built a team that runs perfectly without them constantly stepping in, they're probably not right for a high-growth environment. The best leaders at this level see their job as designing the machine, not being a gear inside it. In the end, scaling a leadership team is really an exercise in unlearning. You have to let go of the exact habits that made you successful in the first place. It's incredibly uncomfortable to move from direct control to systemic influence, but if you don't, the whole organization eventually breaks under its own weight.
The counterintuitive lesson that transformed our leadership scaling was realizing technical excellence often matters less than adaptability. Initially, we prioritized industry veterans with impressive credentials, only to discover that inflexible thinking created silos between departments. This insight prompted us to redefine our hiring criteria, valuing collaborative problem-solvers who could navigate ambiguity over candidates with perfect resumes. This shift fundamentally changed our selection process. We introduced scenario-based interviews focusing on how candidates handle unexpected challenges and their willingness to cross traditional boundaries. We now deliberately seek diversity in thinking styles and backgrounds, creating a leadership ecosystem where complementary perspectives drive innovation. The result has been fewer "perfect on paper" hires and more leaders who thrive amid the constant evolution of our industry and organization.
One counterintuitive lesson: your "best" early leaders can become your biggest scaling bottleneck - not because they're bad, but because what made them great at 5 (heroic execution + tight control) often breaks at 20 (needs systems + delegation + clean interfaces). When we grew from ~5 leaders to 20+, I learned to stop over-valuing "bar-raising functional mastery" and start over-valuing operating-system behavior: - Design repeatable mechanisms (cadences, decision logs, hiring loops, metrics) instead of solving every problem personally - Make work legible (clear written context, ownership, decisions) so the org can move without them - Build leaders rather than accumulating direct reports - Default to clarity over charisma in cross-functional alignment How it changed my future hires: - I shifted interviews from "tell me your biggest wins" to "show me your management system." - I started screening for leverage over brilliance with prompts like: - "Walk me through your weekly operating cadence—what meetings exist, what decisions happen where, and what artifacts come out of it." - "Give an example of a decision you permanently removed from your calendar by creating a mechanism." - "What's a process you killed because it didn't scale?" I began penalizing candidates who sounded like indispensable heroes and rewarding candidates who sounded like architects of autonomy.
The most surprising lesson I learned while growing our leadership team was that technical expertise matters less than learning agility. We initially prioritized candidates with strong industry credentials but found that those who could adapt quickly and embrace new challenges brought more value, regardless of their background. This realization changed our hiring approach. Now, we focus on finding candidates who show intellectual curiosity and resilience instead of just experience in our field. Our interview process includes scenario-based questions that help us understand how candidates deal with uncertainty and whether they have the growth mindset. This shift has helped us build a more diverse leadership team with fresh perspectives that better handle complex problems and adapt to market changes.
Scaling a leadership team from five to over twenty is a significant challenge, especially in affiliate marketing. I've learned that diversity of thought often outweighs experience in leadership roles. Initially, I believed hiring experienced leaders would accelerate growth, but this approach sometimes stifled creativity. In a fast-changing environment, adaptability and innovative thinking are more valuable than a proven track record.
Clarity scales better than charisma. What surprised me most as we built the leadership team at Gotham Artists was how quickly informal leadership breaks under growth. When five people lead, context travels conversationally; at twenty, ambiguity multiplies. The lesson was that structure isn't bureaucracy—it's oxygen. We responded by defining decision rights and success markers far earlier in the hiring process. Future leaders weren't just evaluated on capability but on their ability to operate inside clear lanes while strengthening them. The result was calmer execution and fewer escalations disguised as collaboration. For leaders scaling teams: codify expectations before complexity forces you to. Great leaders don't need constant interpretation—they need unmistakable terrain.
What shocked me the most was that getting more experienced people did not make things easier. For some time, it made everything heavy. Things moved quickly when there were five of us. Because we were all in it together, everyone had the same background. As our age went past twenty, I thought that experience would take care of that. Instead, top hires brought their own strategies, ideas, and ways of doing things. It took me longer to connect than to lead. Inconveniently, that made me think again. I stopped hiring people based on their great pasts and started hiring them based on how they think. Would they be able to handle ambiguity? Could they get clear without being told what to do all the time? Could they change instead of defending what they've done in the past? It changed how we were brought on board too. We made it go slower. We talked about how choices are made, what good judgement means in this case, and areas where we expect disagreement.
When scaling a leadership team, hiring for cultural fit can be more crucial than technical skills. Initially, the focus on technical expertise often disrupted team dynamics due to misalignment with company values. This led to a shift in recruitment strategy, prioritizing cultural alignment to foster collaboration and communication. While technical skills remain important, a cohesive team environment is essential for long-term growth and morale.
I mistakenly thought scaling meant hiring more "star athletes" who shared my aggressive entrepreneurial DNA. I looked for people who wanted to build their own empires, assuming that ambition would drive my company forward. That backfired. We ended up with a locker room full of quarterbacks and no offensive line to protect the pocket. Too many visionaries created operational drag because no one wanted to handle the repetitive, invisible work required to close deals. Now, I hire for complementary temperaments rather than mirroring my own. We actively screen for staff who prefer stability and established processes over the volatility of sales. If I am the gas pedal, I need to hire the brakes. Scaling requires accepting that the people who sustain your growth often look nothing like the person who started the company.
I promoted my best warehouse manager to operations director and watched him quit three months later. That failure taught me the most expensive lesson in scaling: your A-players aren't automatically your future leaders. Here's what happened. This guy was phenomenal at running a 40,000 square foot section of our facility. Perfect accuracy rates, team loved him, solved problems before I knew they existed. When we scaled past $7M and needed someone to oversee multiple facilities, promoting him felt obvious. Wrong. He was miserable. The job required coordinating across sites, managing other managers, sitting in planning meetings instead of being on the floor. He didn't want to lead leaders, he wanted to lead operators. I'd taken my best doer and turned him into a mediocre strategist who hated coming to work. The counterintuitive part? I started hiring for the role two years out, not the role today. When we hit $10M and I knew we'd need a VP of Operations, I didn't look for someone who could manage our current 140,000 square feet. I looked for someone who'd already managed 300,000+ square feet at their last company and was frankly a little bored with our scale. They seemed overqualified on paper. That was the point. This changed everything at Fulfill.com. When we were just launching the marketplace, I hired a CTO who'd built platforms serving millions of users even though we had maybe 50 brands using the system. People thought I was crazy paying that salary for our stage. But when we scaled to 800+ 3PLs and thousands of brand matches, he wasn't learning on the job, he was executing what he'd already done twice before. The insight: hire people who are excited about where you're going, not impressed by where you are. If the role feels like a big step up for them today, it'll feel too small in 18 months. Your best operators rarely make your best executives, and that's not a criticism of them, it's just different wiring. I learned to celebrate people in the roles where they're exceptional instead of promoting them into roles where they'll be average.
The counterintuitive lesson was that adding more senior talent does not automatically improve alignment. Without clear role definitions, leadership overlap creates confusion. Now I focus on clarity of accountability before increasing headcount.