ABOUT THIS EPISODE
What actually happens when a startup starts to scale?In this episode of Let’s Table That, we sit down with Holly, a veteran of the Kitchener-Waterloo tech ecosystem, to talk about the realities of building teams inside growing companies.People Ops wasn’t always seen as strategic. For a long time, it lived in the background, handling things like payroll, policies, and paperwork.But as startups scale, founders quickly realize something: people decisions are business decisions.Holly has spent years helping companies navigate that shift. From early hiring to building leadership teams, she’s seen how culture, structure, and leadership evolve as organizations grow. And she’s also seen where things go wrong.Because scaling a company doesn’t just mean growing headcount. It’s about building the systems, trust, and leadership needed to support all the new hires, and the existing ones too. In this episode, we talk about:• How People Ops evolved from administrative support to strategic leadership• The right time for startups to invest in their first People Ops hire• Why hiring “big company” talent doesn’t always work in startups• The common scaling mistakes founders make• Why copying corporate playbooks can backfire• The difference between managing people and actually leading them• What founders underestimate about the human side of growthIf you’ve ever:• Joined a startup during a period of rapid growth• Wondered when companies should invest in People Ops• Seen culture start to crack as teams scalePull up a chair.---Key Moments:00:00 Introduction02:30 The Evolution of People Ops05:37 When Should Startups Invest in People Ops?10:24 How High-Growth Teams Scale Performance15:00 Common Scaling Mistakes19:20 Being People-First While Setting Boundaries26:26 Leadership Lessons from Scaling Teams28:30 Logic vs. Intuition in Hiring32:00 Feedback in Startups42:48 Under the Table Segment46:00 Leadership in Startups vs. Corporate48:42 HR Horror Stories--- Keep the conversation going: Follow Borderless AI on LinkedIn: linkedin.com/company/hireborderlessConnect with Holly: linkedin.com/in/holly-warwick-4233a6171/Connect with Glaze: linkedin.com/in/glazemartillano Connect with Jazzy: linkedin.com/in/jazmineparrisInterested in diving deeper? Check out our Media Lab: https://www.hireborderless.com/media-lab
