Two Surefire Ways to Get Past Gatekeepers and Talk to CEOs

November 4, 2019

You’re ready to close the big deal.

You know what you’re going to say. You’ve practiced your pitch, memorized every competitor’s offering and worked on your negotiation skills. You’re going to absolutely kill this sale. This CEO is going to buy your product.

You get on the phone, ready to deliver the best sales pitch of your life. And you get stopped by a gatekeeper.

“Yeah, our CEO wants me to gather as much information as possible and present it to her, so you can send me all of your materials,” says this irritatingly effective defender of the executive calendar.

It’s time to make a move. You need to get past this gatekeeper (and any others who stand in your way) and deliver your pitch to this chief exec so you can close the deal.

I have two strategies for you that’ll help get you past gatekeepers and talk to the real decision-makers at a company.

But first, let’s talk about why this is such a crucial skill.

Why Gatekeepers Are the Enemy (Or Are They Really?)

I don’t hate gatekeepers. I really don’t. They’re usually operations professionals who are great at their jobs. And they perform an important function.

Execs are busy, and they don’t want to be interrupted every time a salesperson comes calling. So they install people as an information (and time) filter.

As an executive myself, I totally get it. I respect that decision. As a salesperson, however, I know that gatekeepers can kill a deal faster than you can say . . . well, “gatekeeper.”

And many salespeople start feeling antagonistic toward gatekeepers after a while. If that’s you, adjust your attitude. Nothing good will come out of it. The best salespeople I know actually appreciate gatekeepers. Because they understand that every decision-maker would be inundated with lousy sales pitches, and it would be much harder to actually stand out and get noticed. If you’re a skilled salesperson, and you offer a solution that provides value to the prospect, gatekeepers are actually good for you.

But here’s the problem: no matter how much you tell the gatekeeper about your product, no matter how many information packets you send them, they’ll never be as good at selling your product as you. Even if they’re 100% convinced that the company needs your product, they’re less likely to close the sale to an executive.

Now imagine if they’re not totally sold on your product. They’ll give a half-hearted pitch and leave out important features and benefits—if they remember anything about you at all.

But it’s not your job to convince the gatekeeper. It’s your job to convince the decision-maker.

Which means you need to get to the decision-maker.

Here are two ways to do that.

1. Be an Expert, Not a Sales Rep

Let’s face it: people usually don’t want to talk to sales reps. Especially when they’re already super busy.

But getting around that problem is easy: don’t be a sales rep. Instead, be an expert on your industry, your product and the competitive landscape. Stop pitching your product and start pitching the helpful information that you possess.

Here’s something you might say to a gatekeeper:

“I’m not selling you here. I just want to be available when you chat with the CEO, so when she has questions, she immediately gets a knowledgeable answer. I’ll be there to answer follow-up questions, too. That way we don’t have to schedule another meeting. I know she’s busy—this way will save us all a lot of time and effort.”

Here’s why this technique works so well:

  1. You immediately take the sales pressure off the gatekeeper
  2. You acknowledge the importance and busyness of the CEO
  3. You head off the problem of follow-up questions and meetings before you even get started (seriously, who wouldn’t jump at “we don’t have to schedule another meeting”?)

If you can help the gatekeeper as well as the CEO, even better. Again, this is an operations pro who has a million other sales reps banging on his or her door. They’re not just there to make your life harder.

You can also take a more “consultative” approach with something like this:

“I’m not trying to set up a sales pitch. Think of it like a consultation. I’m very familiar with all of the products in our space, and my priority is to help you choose the right one. I can sit down with you and your CEO to help you figure out which product is the best for your company so you don’t have to listen to pitches from every company out there.”

Again, the emphasis is on helping, not selling. That’s crucial. (Also, with this one, be sure not to come across as sales-y in your meeting. If they think you fooled them into having a sales meeting with you, this deal’s dead.)

Of course, you have to actually deliver on a promise like this. You have to know not just the drawbacks of your competitors’ products, but their benefits as well. If your product is the best, you can be confident in a sale—but remember that sometimes a lead will just go with another option. It happens.

If this method gets you a meeting with the CEO, be sure to keep it quick. If someone values their time enough to hire another person to defend it, you should respect that.

2. Pull the CEO Card

If you think the decision-maker you’re trying to set up a meeting with has a serious case of, “My time is too valuable for sales pitches,” you can use this strategy (though you should probably clear it with your CEO first).

Here’s what you’ll say:

“I get that your CEO doesn’t want to talk with reps from all these different vendors. Because this deal is so important to us, and your CEO needs as much information as possible, I’ll bring in our CEO. They can talk, she can get her questions answered, and we’ll go from there.”

This response has some big advantages:

  1. You acknowledge the importance and busyness of the CEO (see a pattern here?)
  2. You tell the gatekeeper that their company and their decision are very important
  3. It’s much harder to turn down a meeting with another CEO than it is to turn down a sales rep

Whether this meeting is with just your CEO or you and your CEO, you’ve made progress. You might be taken out of the sales equation for now, but you would have gotten rejected anyway. So scheduling a meeting for your CEO is a big win.

Note: the CEO you’re selling to might accept a meeting with a senior VP, director, or other high-ranking employee of your company. But meeting with another CEO will almost always be more appealing.

Again, focus on helping instead of selling here. The more helpful you can be, the more likely you’ll be to get a meeting with the decision-maker on the calendar. You’ll also have to pitch your CEO as being very helpful, and not just a higher-ranking sales rep.

Get in Touch with Every Stakeholder

So far we’ve talked about getting past gatekeepers to talk to CEOs. That’s where I’ve found the most success with these strategies. But there’s a fact we have yet to deal with: there’s often more than one decision.

What do you do in these cases?

The short answer is “the exact same thing.” When the CEO isn’t the only person who will weigh in on this decision, you need to get past as many gatekeepers as you possibly can and personally meet with all the stakeholders you’re able to. Keep your conversations with those stakeholders quick, but make a good impression.

You might not be able to meet with everyone, especially if you’re selling to a huge enterprise. But it’s important to talk to as many stakeholders as possible. Even if you have an internal champion at the company, this is crucial.

And that means you need to sharpen your gatekeeper-passing skills.

Stay in Control of the Sale

The entire point of this exercise is to ensure one thing: that you’re in control of the sale. You don’t want your information filtered through a gatekeeper that may or may not be in favor of this sale.

You also don’t want it filtered through an internal champion, even though they’re on your side.

No one is going to be as good at selling your product as you are. Which is why you need to do everything in your power to be the one who delivers the sales pitch.

This is very similar to the “send me more information” problem. You lose control of what happens next, and that means it might not go your way. When you’re involved in the process, you can guide the lead toward another meeting, a call with your CEO, a demo, or whatever else seems like the best next step in the sales process.

Staying in control goes beyond getting past gatekeepers, too. Whenever someone at the company wants to handle something on their own or says they can do some research without you, it’s in your best interest to offer—tactfully—your help.

Don’t Give Up

Dealing with gatekeepers can be a stressful, disheartening experience for a sales rep (again, nothing against gatekeepers!). But with the right tactics, you can keep the sale moving forward.

The most important thing is to not give up. If you can’t get past the gatekeeper, keep following up. Send emails and make calls. Keep pitching your product and asking to get in touch with the CEO.

Continue being helpful to whoever you talk to—do what you can to get them the information they need and save as much of their time as possible.

Eventually, you’ll make it through that gate.


Steli Efti is the CEO & co-founder of <a href=""></a>, the inside sales CRM of choice for startups and SMBs. Want to get his best startup sales advice? <a href="">Claim your free Startup Sales Success Course!</a>