How to Scale a 100+ Person Team (Without Crashing Margins or Burning Out) with Jack Henderson

If your headcount is growing but your bottom-line profitability and operational control are slipping, your business design is leaking serious cash.  I

In this episode I sit down with Jack Henderson, founder of Henderson Advocacy and one of Australia’s most aggressive operators. Jack went from getting fired from his first buyer’s agency job to scaling a multi-entity brand with over 120 internal employees, 60 advocates, and 1,200+ properties under management in just 24 months. 

He breaks down the harsh truths of rapid headcount growth, why traditional commission-driven models alienate high performers, how to handle toxic hires immediately, and the exact leadership mechanics required to build a high-retention enterprise.  

Tune in to get the direct blueprint for building accountable teams, structuring corporate entities to protect capital, and leading from the front as a founder. 

Key moments:

00:00: Why Hiring the Wrong People Destroys Business Growth

03:33: The Real Cost of Bad Hires

08:36: Why Soft Leaders Avoid Hard Conversations

14:19: How to Fix Broken Commission Structures

17:00: The Real Reason Traditional Agency Models Don't Scale

22:56: How Authentic Personal Branding Outperforms Suits & Studios

27:28: Why Brand Authority Protects You During PR Crises