In sales, the path to closing deals can often feel like a maze. You make calls, send emails, attend meetings, and sometimes, it all feels like you’re knocking on the wrong doors. But what if there was a way to streamline your efforts, focus your energy, and land bigger wins? That’s where the power of starting high in the organization comes in. It’s a strategy that can save you time, build credibility, and help you land the kinds of deals that can change your year.
Too often, salespeople play it safe. They reach out to mid-level managers or lower-level contacts, hoping to work their way up. But starting high—at the executive level—changes the game entirely. It’s not always easy, and it can be intimidating. But if you can get in front of senior decision-makers, you’ll find that the rewards far outweigh the risks.
Why Starting High Works
Here’s the thing about senior executives: they make things happen. Unlike mid-level managers, who are often focused on maintaining the status quo, executives are thinking big. They’re focused on solving problems, driving growth, and achieving strategic goals. When you start high, you’re talking directly to the people who have the power to make decisions—people who can say “yes” without having to ask someone else first.
Think of it like this: if you start at the top and get their buy-in, they can direct you to the right people within the organization, and that introduction carries a lot of weight. Suddenly, you’re not just another salesperson trying to get a meeting. You’re the person who was recommended by the CEO or VP, and that endorsement can open doors that might have otherwise stayed shut.
Breaking the Fear of Rejection
It’s no secret that calling or emailing a senior executive can be intimidating. What if they’re too busy? What if they’re not interested? But here’s the reality—what do you really have to lose? The worst-case scenario is they say no, and you move on. You’re no worse off than if you had never reached out. But the upside? It’s huge. If you get a positive response, you’ve just fast-tracked your way into a high-level conversation that can shape the entire sales process.
Many salespeople fear rejection, but the truth is, reaching out to executives isn’t as scary as it seems. Senior leaders are often more open to hearing from salespeople than you might think, especially if you’re bringing value to the table. They appreciate directness and efficiency, and if you can show that you understand their challenges and have solutions that align with their goals, you’ll find they’re more receptive than you might expect.
The Ripple Effect of Executive Buy-In
Starting high in an organization doesn’t just give you access to a decision-maker—it changes the entire dynamic of your sales approach. When you get an executive’s attention, you’re not just another vendor knocking on the door. You become a trusted advisor, someone who understands their vision and can help them achieve it. This elevates your credibility across the entire organization.
Here’s a scenario: You connect with the CFO of a company, and after a productive conversation, they point you to the head of a specific department. Now, when you reach out to that department head, you’re coming in with a referral from the CFO. It’s no longer a cold call—it’s a warm introduction. And when you’ve got that kind of endorsement, people are much more likely to take your call, respond to your email, and engage with your pitch. It’s like having a golden ticket that sets you apart from the competition.
When to Start High, and How to Do It
Starting high doesn’t mean you abandon all other contacts within an organization—it’s about being strategic with your approach. Here’s when and how to aim for the top:
- When You Have a Strong Value Proposition: If your solution directly impacts the bottom line or addresses a high-level pain point, it’s a good time to start at the top. Executives care about results, so focus your message on the outcomes you can deliver.
- Craft a Tailored Message: An executive’s time is valuable, so you need to make your outreach count. Skip the generic pitch and focus on their specific needs and challenges. Research their recent priorities, initiatives, or challenges and connect them to how you can help.
- Be Direct and Confident: When you reach out, be clear about why you’re contacting them and the value you can provide. Avoid beating around the bush. Executives appreciate when someone can get straight to the point and respect their time.
- Prepare for the Next Steps: If you do get a positive response, be ready with a plan for the next steps. Have ideas about who in their organization you might work with or how you can further explore their needs. This shows you’ve thought things through and are ready to move forward quickly.
The Competitive Edge of Executive-Level Conversations
Here’s the reality: most of your competitors aren’t doing this. They’re playing it safe, sticking with mid-level contacts and hoping those contacts will pass the message up the chain. But when you go straight to the top, you’re taking control of the conversation. You’re positioning yourself as a strategic partner, not just another vendor.
And let’s not forget the difference this can make in your sales results. Deals that come from executive buy-in often move faster, involve larger budgets, and have a higher chance of long-term success. When you’re starting at the top, you’re aligning your pitch with the company’s overall strategy, making it easier to secure larger commitments and deeper relationships.
A Word of Caution: Handle with Care
While starting high has significant advantages, it’s not a magic bullet. You need to be prepared and thoughtful about how you approach these conversations. A poorly planned pitch can backfire if it wastes an executive’s time or comes across as self-serving. So, before you reach out, make sure you’ve done your homework. Know the challenges they’re facing, understand their industry, and be ready to discuss how you can make a real impact.
And remember, even if you start high, you’ll often still need to work with various stakeholders in the organization to get the deal across the finish line. Starting at the top gives you a strong initial advantage, but follow-through is key to turning that advantage into a win.
Reap the Rewards of Starting High
The power of starting high in the organization isn’t just about making a bold move—it’s about being strategic with your sales efforts. It’s about cutting through the noise and getting to the people who can truly see the value of your solution. It’s about positioning yourself as a partner in their success, rather than just another salesperson trying to get a meeting.
By focusing on senior decision-makers, you save time, build credibility, and open up opportunities that might have otherwise stayed out of reach. So, the next time you’re building your target list, don’t be afraid to aim high. Make that call, send that email, and go after the conversations that can make all the difference. Because in the world of sales, those who aren’t afraid to reach for the top often find themselves standing above the rest.
