One of the biggest mistakes roofing contractors make happens early — their first hire.

In this episode, I break down who you should hire first in your roofing business, who you should absolutely avoid hiring too early, and why getting this decision wrong creates years of stress, wasted money, and stalled growth.

If your business still depends heavily on you for sales, phones, scheduling, or finances, this episode will help you make a smarter move and build a company that doesn’t fall apart when you step away.

Hiring your first employee is one of the most important decisions you’ll ever make as a roofing contractor — and it’s also where many contractors go wrong.

In this episode, Dave Sullivan explains why hiring a salesperson too early is usually a mistake, and why your first hire should focus on removing you from the day-to-day chaos, not adding more volume you can’t support.

Dave walks through real-world examples from his own business and from contractors he coaches, showing how the wrong first hire leads to confusion, poor cash flow, and burnout. He explains how outsourcing and administrative support can often be a smarter first step than hiring full-time sales or production roles.

This episode gives you a clear framework to decide when you’re ready to hire, who to hire first, and how to build systems that support growth instead of magnifying problems.

• Your first hire should buy back your time, not add complexity
• Hiring sales too early usually creates more problems than profit
• Systems must come before scaling
• Administrative and operational support often delivers the fastest ROI
• Clear roles and expectations prevent hiring regret
• The goal is a business that runs without you

00:00 – Introduction

04:17 – Why the First Hire Matters So Much

13:51 – The Mistake of Hiring Sales Too Early

24:21 – Outsourcing vs Full-Time Hiring

31:36 – Financial Clarity Before Growth

42:07 – Transitioning from Chaos to Structure

50:30 – Building a Business That Doesn’t Rely on You

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