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5 Insights I Learned While Growing My Business from a Startup to a 500-person Company

5 Insights I Learned While Growing My Business from a Startup to a 500-person Company
5 Insights I Learned While Growing My Business from a Startup to a 500-person Company


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Expanding from a small team to a company with hundreds of employees is a challenging yet rewarding journey. I had this experience with the last company I built: It started with ten people who mostly outsourced services and grew into several autonomous teams with diverse expertise. But the road wasn’t without its bumps.

Many tough decisions (and, of course, mistakes) along the way taught us a lot. So, I’d like to share five key insights from my company’s journey that can help aspiring entrepreneurs grow their businesses.

1. Strategy comes first

As a startup, we were ambitious, thinking big, and expecting rapid growth. We wanted to get our hands busy and jump into business right away. This approach definitely had its advantages at the beginning: we learned on the go and had many important lessons.

However, in time it became clear that everyone on the team had different goals in mind, and we were all moving in different directions. We reacted to immediate challenges rather than working towards long-term goals.

We needed a common vision. Otherwise, growth wouldn’t have been possible.

That’s why we took a step back and focused on developing a strategy that defined our goals and the steps to achieve them. It allowed us to prioritize tasks, allocate resources more effectively, and ensure every team member followed a common path.

So, my advice here is to create a clear roadmap for your business right from the beginning. If all the people work towards one goal, they are more likely to achieve it faster.

2. New team doesn’t mean new managers

According to the U.S. Bureau of Labor Statistics (BLS), around 20% of new businesses fail within their first two years of operation. Fortunately, it wasn’t our case.

Because of our hands-on approach, the business was growing rapidly. However, there was a drawback: our expertise wasn’t catching up. We couldn’t educate our teams quickly enough or expand our knowledge. Since all the team members had been working together for a long time, it was like the blind leading the blind.

Reflecting on this experience, I strongly recommend hiring skilled senior managers who already have the expertise to lead the new business. Of course, you should still invest in your existing team, but don’t demand what they don’t have; give them time to grow. Meanwhile, ensure your business benefits from experienced leadership.

Bringing in highly qualified managers made a difference in our company’s operations. They identified areas for improvement very quickly, which allowed us to handle the increasing workload. Thanks to them, we established a solid foundation for sustainable growth.

Related: Why Middle Managers Are the Key to Your Company’s Success

3. Ideas before data are hypothesis

At the outset of our business, we accepted partnership proposals or started acting on ideas without conducting inner analysis. Some projects seemed to have potential, however, in the end, many of them did not meet our expectations, nor bring strong results.

After a few disappointments like these we learned a simple fact: before data says otherwise, any idea should be treated as a hypothesis.

That’s when data became our guide. We started approaching decision-making with thorough analysis, using data from competitors and hiring leadership who can provide valuable insights from their previous experience. In time, every business step was backed by concrete evidence and strategic insight.

Going from 10 to 500+ people wouldn’t have been possible without this shift. If we wanted to grow, we had to recognize the projects that wouldn’t work out from the beginning.

4. Stick to your strengths

It can be tempting to expand your startup into multiple areas and directions. However, if not done wisely, diversification can drain your business. You should develop products only where you have the expertise and proven results.

Over the years, we maintained a few fully developed products and a team in place, despite the fact they were unprofitable. We held onto them and hoped that something might change. But without a real competitive advantage (which we didn’t have), there was little reason for optimism.

So, to validate our ideas, we conducted A/B testing, using minimal functionality and driving traffic to see the cost per click. Then, we analyzed whether to develop the project or close it.

5. Where there’s structure, there’s accountability

During our company’s startup period, there was no clear distribution of responsibilities. Roles were loosely defined and we were uncertain about who was accountable for tasks.

When we had questions about the project status, we had to consult the entire team without knowing who held the authority. It caused stress both among leadership and employees.

Over time, it just became necessary to implement a structure, but we faced resistance from employees. However, this was perfectly normal: according to Oak Engage’s Change Report, 37% of employees are resistant to change.

To make this process smoother, we held meetings to explain the reasons for the change. The most effective approach was explaining how each change would benefit everyone: what would happen if we implemented the change? What would happen if we didn’t? Later, we initiated general meetings to synchronize the entire company.

As a result of this change, employees became less stressed and more focused on their area of work. It positively impacted their efficiency and, in turn, increased revenue.

Related: How to Start Your Dream Business This Weekend, According to a Tech CEO Worth $36 Million

Transforming a small startup into a big company always comes with challenges, uncertainties and risks. However, it can be a more pleasant journey if you can learn from the experiences of other entrepreneurs.

Prioritizing strategy over tactical decisions, focusing on strong areas and data-proven hypotheses, and being supported by qualified managers and like-minded employees can help you grow your startup rapidly yet smoothly. Finding the balance is the key to successful operations and market expansion.

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