Why Targeting CEOs in Smaller Companies is Your Best Bet for Sales

Why Targeting CEOs in Smaller Companies is Your Best Bet for Sales

Kevin Oliveira

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Oct 17, 2025

Oct 17, 2025

CEO of a small company looking determined
CEO of a small company looking determined

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When you're trying to reach out to potential clients, figuring out who to talk to is half the battle. This approach focuses on a smart way to find the right person, especially if you're dealing with smaller businesses. It's all about making sure your message gets seen by someone who can actually make a decision.

Key Takeaways

  • Go for the Top: In smaller companies, the CEO is often the best person to contact first.

  • Size Matters: Company size dictates your approach; smaller is simpler.

  • Top-Down Works: Reaching out to leadership can lead to introductions to the right people.

The Power of Going Direct to the Top

So, you're sending out emails, trying to connect with people who might buy what you're selling. A common question is, 'Who should I even be emailing?' My strategy? I like to aim high. If you go to the top decision-maker, like the CEO, and they can't help you directly, they'll usually point you to the right person. It's much easier than trying to work your way up from the bottom.

Think about it: if you email someone lower down the ladder, they might not have the authority to make a decision or might just pass your email along, maybe without much enthusiasm. But if the CEO gets your message, they have the power to connect you with the right department or person immediately. It saves a lot of time and effort.

When Company Size Changes the Game

Now, this doesn't mean you should email the CEO of Amazon. Jeff Bezos probably isn't reading cold emails about partnerships. That's where company size comes into play. If you're targeting huge corporations, you might need to aim a bit lower, maybe at directors or managers who handle specific areas.

But here's the sweet spot: for companies with 500 employees or fewer, going straight to the CEO is often the most effective move. These leaders are usually more hands-on and accessible. They're more likely to see the value in a direct approach and respond, or at least direct you appropriately.

A Simple Strategy for Maximum Impact

My advice is pretty straightforward. For businesses up to about 500 people, target the CEO first. If you don't hear back after a reasonable time, then you can try reaching out to the next person down the line. This top-down approach is generally more successful because it cuts through the layers of management. It's about making your initial contact count by going to the person with the ultimate say or the best connections within the company.

Ready to see how a direct, strategic approach can boost your sales? Let's talk about your specific business. Book a strategic discovery call to explore how AI can help you grow your revenue: https://cal.com/kevin-oliveira/ai