Building and scaling a startup is hard, but turning it into an organisation is where things really start to break.
At around 15 to 30 people, what once felt easy suddenly becomes more complex. Communication slows down, expectations become unclear, performance becomes inconsistent, and founders often find themselves stuck in the middle of everything. Many assume it’s a hiring issue, but in reality it runs deeper.
In this interactive session, we’ll unpack the people challenges founders don’t see coming as they scale, brought to life through real stories, honest reflections, and practical insight from working inside growing organisations.
Through a conversational, interview-style format, we’ll explore five of the most common areas where founders underinvest early, and the impact this has as their companies grow.
This isn’t a lecture. It’s an opportunity to step back, reflect on your own business, learn from others in the room, and leave with practical ideas you can apply immediately, whether you are just starting to build a team or already navigating the pressures of growth.
About the Speakers:
Katherine Ray
Katherine works with founders and senior leaders to identify what actually needs to change in their leadership and people approach before it becomes costly as they scale.
With over 20 years’ experience across early-stage, scaling businesses and large global organisations, she brings a broad and grounded perspective on how people and leadership challenges show up at different stages of growth.
As an executive leadership coach, Katherine focuses on helping leaders build the clarity, capability, and confidence needed to lead effectively as their organisations evolve, while enabling teams to perform during periods of growth, change, and increasing complexity.
Kuldish Sibia
Kuldish is a fractional People leader and founder of Scaling People Solutions, with over 20 years of experience across global organisations, scale-ups, and high-growth environments.
He specialises in helping businesses put the right people foundations in place before growth exposes the cracks. From performance challenges to complex people issues, Kuldish brings a practical, no-nonsense perspective on what happens when early decisions start to catch up, and what it takes to fix them.What to Expect on the Night:
You can also listen to these sessions on the Founders500 Podcast:
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