Most founders think scaling is a hiring problem. It’s not, it’s a people problem.
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:
Doors open at 6:15 PM with a welcome drink and networking.
Starting at 6:45 PM, this 75-minute interactive session including Q&A will include:
Real Stories and Insights (Interview Format)
We’ll explore five key people challenges founders face as they scale, including:
- Creating clarity on roles and expectations
- Investing in people management including performance, feedback, and accountability
- Workforce planning, who you hire, when, and why
- How leadership needs to evolve as your company grows
- Building foundations before tools
Each theme will be brought to life through real examples and honest reflections from working with scaling businesses.
Founder-to-Founder Discussion
You’ll have the opportunity to reflect on one of the five key challenges that resonates most with you or is most relevant to your business right now.
Through guided prompts, you’ll explore:
- What’s currently feeling difficult in your organisation
- How this challenge is showing up as you scale
- What you might need to do differently
Q&A
A chance to ask questions and explore specific challenges you’re facing.
Community and Connection
From 8:00 PM, connect with fellow founders, operators, and builders in a relaxed setting designed for meaningful conversation.
You’ll also have the opportunity to speak with Katherine and Kuldish one-to-one about any specific people or organisational challenges you’re currently navigating.
Doors close at 9:00 PM.
Who Should Attend:
- Founders and co-founders building and scaling a team
- Leaders in growing companies where things are starting to feel more complex than they should
- Anyone hiring, managing people, and noticing that what worked early on is no longer working
This session is particularly relevant for companies moving beyond the early stage, around 10 to 50 plus people, where people challenges become more visible and more impactful.
You can also listen to these sessions on the Founders500 Podcast:
Supported by
