Scaling Leadership in Scale-Ups: Key Insights from Our Latest CHRO Community Roundtable

Traditionally, when people think of corporate leadership, they often picture executives at the top of the “corporate ladder”. However, in the fast-paced, ever-changing world of technology companies and scale-ups, leadership takes on many forms. It’s not just about the C-suite - it includes any team leader whose work drives the company’s growth forward. Our latest closed roundtable brought together the CHROs and People Leaders community (including attendees from Lifebit, Hack The Box, Pollfish, Persado, Spotawheel, Skroutz) to discuss the critical challenges and strategies for scaling leadership effectively. The discussion was facilitated by Endeavor Mentor Sofia Kouzinopoulos, Chief People Officer at Kantar Media, formerly Chief People Officer at Vestiaire Collective. Here are some of the key insights that emerged.

Leadership at Scale: When and Why It Becomes Crucial

A recurring theme in the discussion was the timing in which formalized leadership structures become necessary, even urgent for a tech scale up company. Specifically, several of the attendees observed that leadership structures need to be established around the 100–150 employee mark, when oversight by the C-level alone becomes unsustainable. At this stage, executive teams can no longer manage everything directly, making the next level of leadership, or the "C-Level minus 1" leadership, essential to the growth of the company.

When done “right”, these mid-level leaders serve as multipliers, ensuring ongoing, efficient execution and that the company’s vision is communicated effectively throughout the organization. However, without clear role definitions and expectations, companies risk misalignment, inefficiencies, and cultural drift.

Common Pitfalls of Scaling Leadership Teams

As companies scale, structuring and developing multi-level leadership teams comes with challenges. Key issues identified in the discussion included:

• Unclear Roles & Expectations: Without clearly defined leadership responsibilities across different levels within the company, teams operate in silos, leading to misalignment and underperformance.

• Overloaded Leadership Teams: Best practices suggest that no more than 10% of the organization should be in top leadership roles. Too many decision-makers can slow down execution, creating misalignment  and confusion.

• Lack of Leadership Development: Many scale-ups promote talent from within, which helps retain institutional knowledge but can lead to gaps in leadership skills. Supporting these leaders with proper training and clear expectations is crucial. At the same time, distinguishing when to promote internally versus hiring externally is key.

• Founder-Centric Decision Making: Founders often struggle to delegate, leading to bottlenecks and slow decision-making across the company’s operations. Leadership teams must be empowered to act independently while maintaining alignment with company values and their implementation across the organization.

The Different Paths of Leadership Development: The Build vs. Buy Dilemma

One of the biggest questions for any scaling company as it continues to grow is whether to build its leadership team from within through promotions, or hire externally. This can be a challenge for any scale up company at any scaling stage. While internal promotions help retain company culture and previously built knowledge, there’s a risk of promoting employees who may not be ready, and may not have the necessary knowledge and skills to support the company as needed for its subsequent chapter of growth. On the other hand, hiring someone externally can bring much needed, perhaps even missing expertise to the team but it may disrupt existing dynamics, as the new hire may not understand the company’s values and mission, or simply the company may be change-resistant.

The compass to navigating these dilemmas and challenges is intentional decision-making. Leaders must assess where the company is now, where it’s headed, and what type of leadership is needed at each stage of growth. This is particularly critical when transitioning from a 150-person company to a 200+ organization and beyond.

HR’s Role in Scaling Leadership & Managing Complex Dynamics

HR leaders play a pivotal role in helping companies navigate these challenges. Through the discussion, we identified common takeaways and themes for HR professionals which can be found below. 

• Be a Trusted Partner to the CEO: HR should act as a sounding board, helping the CEO see blind spots and providing strategic guidance. This aligns with insights from a previous session with Alexandra Loi, Chief People & Sustainability Officer at ESL FACEIT Group, previously Global Head of HR at Revolut.

• Define and Deploy Company Values: Leadership should reflect company values in hiring, culture, and execution.

• Encourage Delegation & Decision-Making at All Levels: A culture of ultra-centralized decision-making slows progress. HR can help leadership understand why and how to delegate effectively.

• Focus on Culture Add, Not Just Culture Fit: Instead of replicating the same leadership profiles, companies should look for individuals who bring new strengths and perspectives to sustain long-term growth.

The Path Forward: Scaling with Intention

It is essential that, as companies scale, leadership structures must evolve alongside them. The best leaders adapt, delegate, and foster an environment of trust and delegation, where teams feel empowered to drive results, beyond the C-suite. For scale-ups, the challenge isn’t just about growing the business, it’s about scaling leadership in a way that enables sustainable scaling. By addressing these leadership challenges head-on, tech scale-ups can set themselves up for long-term growth and resilience. 

Our roundtable discussions continue to provide a space for CHROs and People Leaders to share insights and shape the future of leadership in scaling companies. If you're navigating similar challenges, we’d love to hear your thoughts!

------------------------------------

About the Community: Endeavor Greece has co-created with Sofia Kouzinopoulou (previously in senior positions at Meta and Vestiaire Collective), a community of HR and People Leaders of scale up companies and leading technology companies in Greece as well as the diaspora with activity in the Greek market. The mission and vision of this community is to promote collaboration, innovation and strategic dialogue between members, offering a communication pathway for the exchange of information, best practices and emerging trends.