Lessons – shifting from startup to enterprise scale

Transformation is essential for scale-up businesses shifting from startup mode to enterprise scale. This phase of growth is full of opportunities and challenges, but businesses that succeed in this journey show that transformation goes beyond adding new processes or tools—it’s about aligning people, priorities, and leadership for sustainable change.

Drawing from companies that have successfully scaled and from the Enterprises I now work with and also have been a leader within for the past 20+ years, here are key lessons that scale-ups can apply to transform and thrive.

1. Leadership Buy-In is Non-Negotiable

Transformation requires everyone to be on board, especially at the leadership level. As seen with Slack’s rise, a clear vision from Stewart and the team, supported by the whole leadership operating as leaders that bring their combined experience to the table, yet can align around this vision (Leadership Stories from Slack), makes all the difference in scaling effectively. Leadership buy-in doesn’t just mean passive support; it’s about active engagement. Leaders who champion transformation create alignment across departments, paving the way for smooth transitions and building trust.

Lesson: Secure the full commitment of your CEO, Board, and executive team. Without strong alignment at the top, transformation efforts will likely stall. Consider appointing a transformation lead in your C-suite to drive and maintain focus on long-term goals.

2. Transformation Takes Time

The path from a startup to an enterprise is often longer than expected, but patience pays off. Atlassian’s journey from a small, scrappy team to a global player wasn’t an overnight success—it resulted from continuous, incremental improvements (From 0 to 1 at Atlassian). For scale-ups, quick wins are essential to create traction and keep momentum, but there also needs to be a long-term view and the understanding that true transformation takes time.

Lesson: Set realistic expectations with stakeholders about the transformation timeline. Highlight quick wins to build momentum, but be transparent that the journey will require sustained effort and patience.

3. Prioritize the Right Changes

Not every change is equal in importance or impact. It’s critical to focus on foundational elements that support reuse, scalability, and adaptability. Amazon’s journey over the starting 5-10 years demonstrates the value of staying focused on what truly matters: long-term customer value and operational efficiencies. A balanced scorecard can be useful here, helping you align on goals, methods, and measures to keep everyone on track.

Lesson: Prioritize changes that enable repeatability and scale, like those impacting core processes, technology, and cultural alignment. A clear focus on foundational elements creates a stable base for continued growth.

4. Communication and Transparency

Effective communication is one of the most important aspects of transformation. HubSpot’s growth was powered by a culture of open communication, which ensured that teams were aligned and motivated throughout periods of rapid growth. With clear channels, everyone knows the “why” behind each change, building trust and engagement from the ground up.

Lesson: Keep your teams informed. Transparency builds trust and keeps teams engaged. Use a variety of communication channels—whether synchronous, asynchronous, text, or video—to make sure all voices are heard.

5. Celebrate Wins and Learn from Mistakes

Transforming at scale isn’t without challenges, and mistakes will happen. However, every error is a learning opportunity. Netflix’s culture of openness to change and willingness to learn from missteps (Netflix Culture) helped shape the company into the innovative giant it is today. Celebrating successes, including mistakes, helps to foster resilience and adaptability within the team.

Lesson: Recognize and celebrate progress, big or small. By doing so, you keep morale high and maintain momentum. View mistakes as lessons that guide future decisions, creating an environment where teams feel safe to innovate.

Scaling with Purpose

Moving from startup to enterprise scale is a complex journey that requires more than just new processes—it needs alignment, communication, and a commitment to continuous improvement. By embracing these principles, scale-up businesses can transform purposefully and build a strong foundation for enterprise success. Each of these elements—leadership buy-in, patience, prioritization, communication, and resilience—has proven essential for companies that have mastered this transition.

The journey may be challenging, but with a focus on these transformative elements, your organization can turn growth potential into sustainable success.

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