Founders: When to Let Go of Sales

As a Founder or CEO, every decision you make shapes the future of your company. But if you’re still managing sales yourself, you’re holding the business back. In this video, I share why founders must learn to let go of day-to-day sales management to scale effectively. Founders start out leading sales because they know their product best. But staying in that role too long drains energy, limits growth, and prevents the business from scaling. Fractional sales management gives you a proven framework to replace founder-led selling with a structured sales process, sales leadership, and accountability—without the cost of a full-time VP of Sales. You’ll see how making the right decision—handing sales leadership to a pro—unlocks growth, builds a scalable sales team, and frees you to focus on strategy, funding, and vision. If you’re a Founder, Entrepreneur, or Small Business CEO struggling with sales, this video is for you. Learn how to stop pouring time into sales management and start building a team that sells without you. The 3 Biggest Takeaways Get in the Trenches or Get Out of the Way You cannot expect your sales team to execute on tasks you are unwilling to do yourself. Your team needs to know you have been into battle before. If you sit in an ivory tower demanding 50 cold calls a day but refuse to pick up the phone yourself, you don’t have a sales team; you have a group of employees who secretly resent you. Respect is earned on the sales floor, not in the boardroom. Show, Don't Just Tell "Leading by example" isn't a metaphor; it’s a tactical instruction. Sit down and make cold calls with them. Open up your laptop and show them exactly how you prospect. When they see the Founder or VP of Sales getting rejected and keeping their cool, it removes the fear. When they see you book a meeting, it proves the process works. Leverage Your "War Stories" for Training Your past success is their current playbook. Don't hoard your knowledge. Give them the exact words and scripts you used to build the business in the early days. Better yet, call one of your legacy customers and put them on speaker (or Zoom) so your reps can hear why they bought from you. That is the most powerful training material you can possibly provide. Frequently Asked Questions (FAQs) Q1: I haven't cold called in 10 years and I'm rusty. Won't I look stupid if I fail in front of my team? A: No, you will look human. In fact, failing in front of them is almost better than succeeding. It shows them that rejection is part of the game and that even the boss gets told "no." It gives them permission to fail without fear, provided they get back up and dial again. Q2: I’m the CEO; I don't have time to sit and make calls with reps. How do I balance this? A: You don't have time not to. If your sales team fails, your company fails. You don't need to do this all day, every day. Dedicate one "power hour" a week to selling alongside them. The ROI on that hour—in terms of morale and culture—is higher than almost any meeting on your calendar. Q3: My old scripts from 5 years ago feel outdated. Should I still share them? A: Yes, but frame them correctly. The tactics might have changed, but the psychology hasn't. Share the scripts to show how you handled objections and built value. Then, work with the team to update the language for today's market. It’s a collaborative exercise that builds buy-in. Q4: Why should I have reps talk to my old customers? Isn't that risky? A: It’s only risky if you didn't deliver value. If you did, those customers are your biggest advocates. Hearing a client say, "I bought from Louie because he understood my pain points, not because he had a flashy pitch," teaches your reps that empathy sells better than features. Q5: Is this micromanagement? A: Absolutely not. Micromanaging is hovering over their shoulder asking, "Why haven't you done this?" Leading by example is sitting next to them saying, "Watch me do this, then let's do it together." One breeds anxiety; the other breeds confidence.