Navigating the Waters of Startup Leadership: A Founder’s Journey

March 6, 2024

Just over 12 months ago, I found myself sitting on a beach in Abu Dhabi, surrounded by the breathtaking scenery of Saadiyat Island—a destination I highly recommend.

On paper, my company was thriving, with strong revenues and a clear path to exit, particularly over the previous two years. However, during this period, my focus was more on filling positions rapidly rather than on the quality of staff, a situation further complicated by the challenges of COVID-19. This oversight became glaringly evident during a critical juncture: I had sent my senior leadership team to represent us in exit discussions, facilitated in part by KPMG. Due to travel restrictions, I couldn’t be in London for these meetings. It was then that KPMG relayed a disconcerting message: the buyer’s interest had waned, citing the conduct and caliber of my executive team as major concerns. They pointed out that I had inadvertently presented a C-class team to the buyer, a misstep that jeopardized the entire deal.

This revelation led the buyer to question the caliber of the wider team working under these executives. Their concerns were valid; the reality was that the staff mirrored the deficiencies of their leaders. The lack of diligence in our hiring process had not only affected the executive tier but had trickled down, influencing the overall quality and effectiveness of our entire workforce. This was a harsh but necessary wake-up call, highlighting the critical importance of leadership quality and its direct impact on a team’s performance and, ultimately, on the company’s valuation.

This led to a pivotal realization: my dream of a massive exit might not materialize. I want to share my experiences and insights from this period, helping you avoid similar pitfalls and highlighting how I redirected the course to develop the successful business I run today.

The most significant error I made was hiring individuals outside of our industry and giving them immediate decision-making power without allowing them sufficient time to understand our domain. In a high-growth, scaling environment, the luxury of time for extensive education and training is often scarce. I employed people from larger enterprises accustomed to more structured environments—a stark contrast to the scrappy, agile nature of a startup. This mismatch in expectations led to growth challenges and internal tension, and I failed to identify this disconnect as a root cause of our problems—a major oversight on my part.

In retrospect, I wish I had spent more time evaluating each candidate. Had I done so, I suspect I wouldn’t have hired 80% of that team, saving hundreds of hours spent addressing operational issues caused by their lack of understanding and direction. These team members, while not inherently problematic, were not solution-oriented and contributed to a toxic environment.

The concept of A-Team, B-Team, and C-Team players is something I’ve encountered repeatedly. Your company should not harbor C-Team players—if identified, they need to be let go immediately. B-Team players, destined to become A-Team contributors within six months, should already grasp the rules of the game and possess the skills to advance based on merit, not training. Those who don’t meet these criteria must be let go. A-Team players, the backbone of your organization, require minimal management and inherently understand and drive your vision. Unfortunately, most of my team consisted of B and C players, with only about 5% being A-Team material. This imbalance made retaining top talent amidst mediocrity a near-impossible task, exacerbated by the fact that many of my executives were at best C-Team players.

I don’t fault these B and C players; the accountability rests with me. It was my investment and my responsibility. I also owe them an apology for not recognizing sooner that they were not the right fit, thereby prolonging their false hope.

So, back to that beach in Abu Dhabi. It was there that I resolved to start anew. In the following five months, I focused on envisioning a new, product-centric platform. I redesigned everything from the product itself to the technological architecture, keeping these developments confidential until I had a viable proof of concept. Subsequently, I rebranded and assembled a smaller, more agile A-Team. Today, we’re delivering more personalized experiences than ever before at my previous venture.

I’ve partnered with Oliver from Behind the Login to discuss this transformative journey and our collaborative approach to product development and deployment. You can find the podcast link here. As always, I welcome your feedback and comments.