How to Scale a Sales Team in Security (What Actually Works)

How do you scale a sales team inside a security or life-safety business—without hiring too fast, burning cash, or building a “hope-based” sales org?In this episode of Entry & Exit, hosts Stephen Olmon and Collin Trimble break down the exact framework they’ve used at Alarm Masters to grow from founder-led selling to a six-person sales team—and the systems that make it repeatable. They cover quota math (3–5x coverage), segmented sales roles (hunters vs. farmers), the KPIs that prevent surprises, and why face-to-face wins in this industry.You’ll also get real-world guidance on hiring, ramp expectations, building playbooks, and how to design your sales process around a clear value proposition—so your reps don’t default to discounting when pressure hits. Plus, they share quick updates on what’s happening at Alarm Masters, including new add-ons and expansion plans across Texas.What You’ll LearnWhen to hire the next salesperson: The “pay for the next rep” principle (and how to apply it without waiting a full year)Quota math that actually works: Why 3–5x OTE coverage matters—and a simple way to think about itSegmented sales strategy: Why you shouldn’t expect one rep to do everything (and the roles to hire first)Hunters vs. farmers (install base): The difference between new-logo selling and expanding existing accountsLeading indicators & KPIs: Pipeline coverage, close rate, average deal size, conversion rates, and sales cycle lengthThe gospel of face-to-face: Why more in-person time increases win rate and reduces attritionSales process + value prop alignment: How “we’re the Chick-fil-A of security” shapes the entire sales motionPractical ops reminders: Contract audits, customer communication, and why intentionality beats hoping it works🔗 ConnectStephen Olmon Collin Trimble More Entry & Exit Owned and Operated New Episodes Every Wednesday!Subscribe For More