Top 5 Mistakes Founders Make Trying to Scale

Over twenty years of scaling B2B SaaS and tech-enabled services companies, I’ve watched businesses face remarkably similar challenges as they hit new revenue milestones. Some break through and build repeatable, profitable growth. Others get stuck and lose momentum. The mistakes are predictable, and they’re avoidable.

Mistake #1: Being Too Opportunistic

The agility that powered early growth becomes a liability at scale. Founders who built their companies by saying yes to everything find that the same instincts now scatter resources and prevent focus.

I’ve seen this manifest in predictable ways. The product roadmap is stretched thin, catering to too many different client demands. Operations are constantly compensating for half-baked functionality. The GTM strategy lacks focus, leading to inconsistent pipeline and missed quotas. And margins stay flat because the company can’t grow revenue without adding bodies.

The hardest part is that founders often frame this as a virtue. “We’re nimble. We’re responsive to our customers.” But there’s a difference between responsiveness and reactivity. Scale requires the discipline to say no: to opportunities that don’t fit, to customers who aren’t ideal, to features that serve edge cases. The companies that break through are the ones that learn to reduce and simplify, not expand and accommodate.

Mistake #2: Founder Bottlenecks

In the early days, founders drive every major decision and manage key client relationships. This works when you’re small. It breaks down quickly as you grow.

The symptoms are easy to spot. The founder is still involved in operational decisions that should be delegated. There’s no competent middle management layer. Decisions queue up waiting for the founder’s attention, and the organization learns to wait rather than act.

The shift required here is fundamental: founders must stop working in the business and start working on it. This sounds like a cliché, but I’ve watched founders struggle with it for years. The behaviors that made them successful in the early days—hands-on problem-solving, deep client relationships, personal attention to detail—are exactly what they need to delegate. The job changes from doing the work to creating the conditions for others to do it well.

Mistake #3: No Real Systems

As businesses grow, one of the most commonly exposed weaknesses is the reliance on heroics. Success depends on a few people who know how to exploit the quirks of the tools, who carry institutional knowledge in their heads, who make things work through sheer effort and tribal knowledge.

This is sustainable at small scale, but it breaks down as you grow. Production processes are inconsistent. Sales teams get bogged down in operations. Every challenge gets the same answer: “We need more people!” But no one can explain why, or whether the work could be done more efficiently with better systems.

The solution isn’t complicated: establish clear, scalable processes with defined roles. But the implementation is harder than it sounds, especially for founders who’ve never built operational infrastructure before. Sometimes this means bringing in outside expertise—not because the team is incompetent, but because building systems at scale is a distinct skill that most early-stage teams haven’t had the opportunity to develop.

Mistake #4: Letting Complexity Compound

Complexity multiplies geometrically as a business scales. Early on, a small leadership team can oversee most activities through direct involvement. That breaks down quickly as you add people, products, and customers.

The warning signs are familiar. Each team sets its own priorities without coordination. Communication breaks down across functions. Culture drifts as new hires don’t absorb the company’s values. The organization loses the agility it once had, leading to slower execution and rising frustration.

In my experience, this is where many founders lose interest. Managing complexity feels like administrative overhead—meetings, alignment sessions, communication processes—rather than “real work.” But this is the work at scale. Building the structures that keep everyone aligned, setting clear priorities, maintaining a cohesive culture: these aren’t distractions from growth. They’re prerequisites for it.

Mistake #5: Chasing Logos You Can’t Serve

Enterprise clients are seductive. They bring prestige, revenue, and investor approval. They also demand heavy customization, long sales cycles, and high-touch service that can break a company that isn’t ready.

I’ve seen this play out painfully. Sales teams invest months pursuing enterprise deals with no guarantee of success. When they do close and realize they have a tiger by the tail, everyone scrambles to meet their needs—CS teams especially. Standardized delivery gives way to bespoke service. Margins erode. Cash flow suffers from long payment cycles. And the smaller clients that actually fit the model get neglected.

The goal isn’t to avoid enterprise clients. It’s to land them profitably. That requires honest assessment of whether your infrastructure can support their demands without compromising everything else. Sometimes the right answer is to wait until you’ve built the foundation to serve them well.

The common thread

These five mistakes share a root cause: founders scaling the company they have rather than building the company they need.

The scrappy, opportunistic, founder-centric, heroics-driven organization that got you to $5M or $10M in revenue will not get you to $50M. The transition requires letting go of what worked before—not because it was wrong, but because it won’t work anymore. That’s harder than it sounds. The instincts that made founders successful are deeply ingrained. Changing them feels like abandoning what got you here.

For PE investors and operating partners, these patterns are worth watching for during diligence. A company stuck on one or more of these mistakes isn’t necessarily a bad investment—but it will require deliberate intervention to fix. The earlier you identify the issues, the faster you can build a value creation plan that addresses them.

If you’re facing these challenges, I’m happy to talk through them.