5 Minutes with Sara Roberts: Interview Three of Three

Collingwood's Managing Director, Doug Mackay, recently sat down with HealthTech, Wellbeing, Longevity and IaaS entrepreneur, Sara Roberts to discuss her experience with early-stage team building and executive recruitment strategies.

Sara is a purpose-driven operator with 15+ years’ experience in scaling ventures across HealthTech, Wellbeing, Longevity, and IaaS. From Europe to Africa to the US, she has built and led businesses from the ground up, taking them from concept to £10m+ ARR, while delivering measurable impact and sustainable growth. External to this, Sara sits on the Advisory for the International WELL Building Institute, transforming health and well-being with our people first approach to buildings, organisations and communities.

Scaling Leadership - From Doers to Drivers 

Doug: At what point in a company’s growth do you start feeling the shift from needing generalist 'doers' to bringing in experienced specialists, and how do you know it's time?

Sara: I have always believed in building robust foundations, processes, systems, and people that can scale, almost from the outset of starting a company. I am also an avid supporter of having generalists in the business, particularly in high-growth environments. They’ve been in different seats,  seen things from different sides and so in the event of needing to pivot and adapt, they are much more agile and suited to a high growth environment.

However, too many generalists and cracks can form. I have seen this around a team size of 25, project plans getting lost in translation between product and customer success, or new starters not knowing who to ask when they had a question! At this point building in a tolerable layer of hierarchy, with the inclusion of experienced specialists can continue the high growth trajectory. 

Doug: What signals tell you it's the right moment to bring in external executive talent versus promoting from within?

Sara: I look at three things:

• Capability – Does the internal person have the skillset for where we’re going, not just where we’ve been?
• Credibility – Will they be seen as a peer in the room we’re entering next?
• Capacity – Do they have the time, space, and support to grow into the role fast enough?

If the answer to all three is yes, promote. If not, bring in outside experience and build a growth path internally.

Doug: Have you ever faced resistance from early team members when scaling leadership, and how did you navigate that transition without losing trust?

Sara: Absolutely. Early team members often fear being side-lined.

The key is framing: this isn’t about replacing them, it’s about reinforcing the mission. I’m honest about what’s needed at the next stage and make sure they’re part of the transition, not blindsided by it.

I also double down on recognition. I remind them: you built this. And now we’re bringing in more hands to help it grow.

I also believe that this is something as a founder you need to be aware of in terms of your own skillset; knowing when and if the time is right to bring in someone to lead the business further.

Doug: What traits help early team members successfully evolve into scale-stage leaders, and how do you support that growth?

Sara: Self-awareness and humility are huge. The ones who scale well are open to feedback, hungry to learn, and willing to unlearn what no longer serves.

I support them by offering coaches, clear development plans, and stretch roles. But more than anything, I create safety, a space where growing pains are normal, not penalised.

Doug: When partnering with executive recruiters during this phase, what qualities or approaches make them a true strategic asset rather than just a hiring service?

Sara: Great recruiters don’t just fill roles, they help shape teams.

The ones I value most ask deep questions about culture, friction points, and team maturity. They act as mirrors, reflecting back where we’re strong and where we’re stuck. They challenge my assumptions, widen the search lens, and bring candidates I never would’ve found on my own.

They don’t just place talent, they build resilient teams.

This is a series of 3 interviews with Sara to help owners and entrepreneurs to build high performing teams. Find interview one here and interview two here.

If you're interested in working with Sara, contact her via email today.

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