Building a company from the ground up is an exhilarating journey filled with unexpected challenges. At Hawke Media, we grew to 250 people in under ten years, and this rapid growth taught me something crucial about business evolution that isn’t discussed enough.
Every time your headcount doubles, your entire organization transforms. This isn’t just a minor adjustment—it’s a complete reinvention of your culture and operations.
I’ve lived through these transitions: 10 to 20 employees, 20 to 40, 40 to 80, 80 to 160, and beyond. Each phase required us to fundamentally rethink how we operated. What worked brilliantly at 40 people often failed miserably at 80.
The Transformation Cycle
When your team size doubles, several critical elements need immediate attention:
- Infrastructure requirements change dramatically
- Management structures need reorganization
- Communication systems must evolve
- Cultural dynamics shift in unexpected ways
- Decision-making processes require new frameworks
These changes aren’t signs of failure—they’re markers of growth. My business partner made an excellent comparison: these transitions mirror life stages like moving from middle school to high school, or college to the professional world.
Each stage brings unique advantages and challenges. The intimate, everyone-knows-everyone culture of a 20-person startup gives way to the more structured environment needed for 80+ employees. The scrappy, all-hands-on-deck approach that works for smaller teams becomes chaotic and inefficient as you scale.
Embracing the Evolution
Many founders resist these changes. They cling to “the way things were” in the early days, viewing each necessary evolution as a loss of the company’s soul. This resistance to change is one of the biggest killers of growing businesses.
I’ve learned to see these transitions differently. Yes, there’s often nostalgia for earlier phases—just as we might reminisce about college days—but progress brings new opportunities and challenges that can be equally rewarding.
The key is recognizing when you’ve hit these inflection points and proactively reshaping your organization rather than waiting for problems to emerge. At Hawke, we’ve sometimes made this mistake, holding onto structures or processes too long after we’d outgrown them.
Every time your headcount doubles, your culture and your operations completely change.
When we doubled from 40 to 80 people, we maintained our flat management structure too long. The result? Communication breakdowns, unclear expectations, and frustrated team members. We eventually built out proper middle management, but the delay caused unnecessary pain.
Planning for Phase Shifts
If you’re growing a business, prepare for these transitions before they arrive. Here’s what I recommend:
- Identify the systems that will break under twice your current load
- Plan management structure changes before they become urgent
- Document culture values so they survive structural changes
- Talk openly with your team about upcoming transitions
Growth doesn’t have to mean losing what made your company special in the first place. The core values can remain while the expression of those values evolves.
These business phases, like life stages, each have their magic. The startup phase brings the thrill of creation and close-knit teams. The growth phase offers new challenges and opportunities for team members to specialize and develop. Maturity brings stability and the chance to make a larger impact.
Don’t fight the natural evolution of your company—flow with it. The business you build through these transitions will be stronger, more resilient, and better positioned for long-term success than one that tries to stay frozen in time.
Frequently Asked Questions
Q: How do I know when my company is approaching a growth phase that will require restructuring?
Watch for signs like communication breakdowns, decision bottlenecks, and team members expressing confusion about roles or reporting structures. These typically emerge before you actually double in size and serve as early warning signals that your current structure is reaching its limits.
Q: What aspects of company culture are most vulnerable during growth transitions?
The informal communication channels and sense of unified purpose often suffer first. As teams grow and specialize, silos naturally form. Without intentional effort, the shared mission and cross-team collaboration that came naturally in smaller stages can quickly disappear.
Q: Should I hire ahead of growth or wait until we’re feeling the strain?
I’ve found that hiring key management positions slightly ahead of acute need works best. This gives new leaders time to understand the company before they need to build and manage expanded teams. Waiting until you’re already feeling significant growing pains often leads to rushed hiring decisions and longer adjustment periods.
Q: How do you maintain the founder’s vision through multiple growth phases?
Document your core values and mission early, then reinforce them constantly through multiple channels. As you add management layers, invest significant time ensuring these leaders deeply understand and can authentically represent the vision. Regular all-hands meetings, consistent messaging, and stories that illustrate your values in action help maintain continuity through growth.
Q: What’s the biggest mistake you’ve seen companies make during growth transitions?
The most damaging mistake is failing to acknowledge that change is necessary. Many founders try to preserve everything about their early-stage company, refusing to add needed structure or management layers because it feels corporate or bureaucratic. This creates dysfunction as the organization outgrows its structure. The companies that thrive recognize that evolution is not just inevitable but necessary for continued success.
