Navigating Leadership Evolution: A Simplified Transition Model from Startup to Scale-Up

Transitioning from startup to scale-up requires leaders to shift from hands-on roles to more strategic positions. This discussion examines the approach recommended in the article “How to move from a startup founder to a scale-up founder” by Colin Hewitt, and looks to analyse the article, the approach, make recommendations for improvement by simplifying the initial five-role model into a three-role framework – Executive, Manager, and Executor, aiming to ease this transition. By offering visual representation, real-world examples, personalized assessments, and mentorship, we aim to provide a clear, value-added pathway for leaders evolving alongside their growing organizations.



In the article, “How to move from a startup founder to a scale-up founder” authored by Colin Hewitt, the narrative discusses the transition journey of a startup founder evolving into a scale-up founder based on his own experiences at Float, a startup he co-founded. The piece sheds light on the challenges associated with this transition, such as lack of focus due to constant fire-fighting and the need for a shift from an operational to a more strategic role. Hewitt provides tangible solutions like adopting an Entrepreneurial Operating System (EOS), restructuring time management to allow strategic thinking and the practice of journaling to facilitate this transition. While he shares a personal affinity for operational roles, he advocates for a necessary evolution towards strategic roles to ensure business growth and sustainability.

Critical Analysis

Colin Hewitt’s piece serves as an insightful guide for startup founders facing the daunting transition to scale-up founders. He underscores real challenges like loss of focus and the inherent operational whirlwind at the startup phase, which many founders can relate to. His account also offers practical advice such as adopting EOS, realigning the roles of a CEO, scheduling strategic thinking time, and journaling. These suggestions are pragmatic and could be applied with relative ease.

Nevertheless, there are some areas where the advice could be refined or expanded upon. For instance, while EOS has worked for Float, the narrative could have benefitted from exploring alternative systems or frameworks, catering to a broader audience. A comparative analysis of different frameworks would provide a more rounded perspective to readers and enable better-informed decisions.

Moreover, the transition from being operationally focused to strategically inclined is depicted as an essential evolution. However, the emotional and psychological challenges attached to letting go of operational control are briefly touched upon. A deeper dive into how founders can mentally and emotionally navigate this transition would have been a valuable addition to the discourse.

Additionally, the article leans heavily on Hewitt’s personal experiences and preferences, which, while providing authenticity, may not resonate with or be applicable to a wider audience. Broadening the narrative to include experiences and strategies from other startup founders could provide a more holistic view and diverse range of tactics for managing this transition.

Lastly, while Hewitt mentions the importance of senior hires and helping team members transition into senior leadership roles, he doesn’t delve into how to effectively identify, train, or transition these individuals. Offering strategies or insights on building a competent leadership team could significantly bolster the practical utility of the article, given the crucial role a strong leadership team plays in scaling a business.

Hewitt’s narrative is a valuable read for startup founders on the brink of scaling up. It offers tangible advice gleaned from personal experience. However, a broader perspective exploring alternative strategies, emotional challenges, and the creation of a robust leadership team would have enriched the advice and widened its applicability.

Model as Discussed

The model discussed in the text outlines the evolutionary roles a CEO or founder may undertake as a startup transitions into a scale-up phase. Here’s a breakdown of each role and how they relate to the transition from startup to scale-up:

  1. Strategist:
    • Involves long-term vision and strategy formulation.
    • Crucial for setting the direction of the company as it scales.
  2. Ambassador:
    • Centers on building external relationships, partnerships, and garnering support from stakeholders.
    • Becomes increasingly important to gain credibility and resources in the scaling phase.
  3. Orchestrator:
    • Concerned with aligning resources, processes, and teams to execute the strategy.
    • Ensures the various parts of the organization are harmoniously working towards common goals.
  4. Captain:
    • Involves day-to-day management, making crucial decisions, and leading teams.
    • Vital in the early stages to navigate through challenges and maintain operational efficiency.
  5. Operator:
    • Encompasses hands-on tasks and immediate problem-solving often prevalent in the startup phase.
    • Important for overcoming initial hurdles and maintaining momentum.

In the startup phase, a founder or CEO may find themselves acting more as an Operator or Captain, dealing with day-to-day operational challenges and making crucial decisions to keep the business afloat. However, as the business grows, matures, and perhaps diversifies into different departments, the leader’s role needs to evolve to ensure sustainable growth.

The model suggests that as the business transitions into the scale-up phase, the leader should gradually shift their focus from operational (Operator/Captain) to more strategic and outward-facing roles (Strategist/Ambassador) while also ensuring organizational alignment (Orchestrator). This transition is particularly necessary as more senior hires are brought on board, and other team members rise to leadership roles, thereby filling the operational and managerial gaps the CEO originally covered.

The narrative also touches on the emotional and practical challenges of letting go of certain operational control, using a light-hearted example of choosing coffee for a larger team. This highlights the necessary yet sometimes difficult process of delegating tasks and responsibilities, which is crucial for freeing up the leader’s time to focus on broader, long-term strategic issues vital for scaling the business.

Simplified Model

The model outlined is essentially a framework guiding CEOs on how to transition their roles as their companies evolve from startups to more established entities. It defines five roles, each with distinct responsibilities and focus areas. The idea is to help leaders identify where they are spending most of their time currently and where they should be allocating it as their organizations grow. Here’s a simplified breakdown of this model and how to make it easier to understand and more valuable:

  1. Simplifying the Model:
    • Condense the Roles: Consolidate the five roles into three broader categories:
      • Visionary (Strategist + Ambassador): Focused on long-term strategy and external relations.
      • Manager (Orchestrator + Captain): Engaged in day-to-day operations and team management.
      • Executor (Operator): Involved in the hands-on tasks and immediate problem-solving.
    • This condensation simplifies the transition process and lessens the complexity of managing multiple nuanced roles.
  2. Easing Understanding:
    • Visual Representation: Create a visual chart or diagram illustrating the three roles, what they encompass, and how the focus should shift from one to the other as the company grows. Visual aids can provide a clearer understanding.
    • Real-world Examples: Offer real-world examples or case studies demonstrating how shifting roles have positively impacted other organizations.
  3. Increasing Value:
    • Personalized Assessment: Implement a self-assessment tool or a facilitated workshop where leaders can evaluate their current time allocation across the simplified roles, and receive personalized recommendations for transition.
    • Mentorship and Training: Offer mentorship programs or training sessions to aid in developing the necessary skills for the new roles they need to transition into. This not only clarifies the model but adds value by promoting personal and professional growth.
    • Feedback Loop: Establish a feedback mechanism to continuously assess and adjust the role transition process. This could involve periodic reviews with peers, mentors, or an advisory board.

By streamlining the roles, providing visual and real-world examples for better comprehension, and implementing personalized assessments, mentorship, and a feedback loop, this model can become simpler, more understandable, and significantly more valuable to individuals navigating the transition from startup to scale-up leadership.


The shift to scale-up leadership is crucial for organizational growth. This article’s simplified three-role model facilitates a smoother transition from operational to strategic roles for leaders. By reducing complexity and adding value through mentorship and feedback, this framework seeks to ensure a successful evolution from a startup to a mature, scalable operation, positioning leaders effectively for long-term organizational success.