How to Get Past the Gatekeeper and Make Sales

Donald Kelly’s first encounter with gatekeepers as a salesperson happened when he was selling candy bars to other kids in middle school.

It didn’t take him long to realize that, while kids love candy bars, they don’t have a lot of cash on hand — so the real candy bar buyers were actually the parents. To make the sale, he needed to make his case directly to parents, but first, he had to convince the gatekeepers — the kids — to make introductions.

It sounds simple, but getting the introduction requires earning the gatekeeper’s trust and equipping them with useful information to champion your cause. People don’t like looking bad in front of their bosses... -er — parents.

“You want to get to know the parents so you can help the parents see that Donald is a good kid, and he’s someone of worth,” Kelly said. “When you can empower your gatekeeper, those individuals can go back and bring you to the decision-maker who holds the purse.”

It’s been a long time since Kelly sold candy bars, but the experience has stuck with him throughout his sales career. Whether he was selling spring cleaning services as a high schooler or now, as the founder of the tech sales training firm The Sales Evangelist, there have always been gatekeepers standing between him and the decision-maker.

“When you can empower your gatekeeper, those individuals can go back and bring you to the decision-maker that holds the purse.”

In tech sales, the gatekeeper might be an executive assistant who books meetings, or an employee who wants your product but doesn’t have purchasing power. While sales reps may not be excited about not having another go-between, they are only making their lives more difficult trying to out-maneuver gatekeepers. There’s a more effective way.

Much like in the child and their parents in the candy bar example, gatekeepers possess a valuable relationship with the decision-maker. Rather than treating the gatekeeper as an obstacle to get past, Kelly has learned that a sales rep can get a lot farther in their efforts if they try to work with them instead.

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Treat the Gatekeeper With Respect

Every gatekeeper has their own job to do, and it’s not making the lives of sales reps more difficult.

This may seem obvious, but in the mad dash to hit quota, Kelly has seen plenty of reps who start treating gatekeepers like obstacles to get around rather than actual people. Doing so is a one-way road to rejection.

In Kelly’s view, the single most important thing a rep can do to improve their chances with a gatekeeper is to treat them with respect.

It starts with understanding their role. When a gatekeeper is an executive assistant, part of their job is to protect their executive’s time. That doesn’t mean that they’re trying to prevent any meeting from being booked, though. Rather, they’re trying to eliminate meetings that don’t align with the executive’s organizational goals.

“The way that has worked for me is to be honest, be upfront and to be forward with them in a professional way,” Kelly said. “Understand what they’re doing and see how you can help them.”

Perhaps the worst thing a sales rep can do is to lie to the gatekeeper or to push them over, added Displayr Major Account Executive Alexine Mudawar. Even if the gatekeeper is a lower-level employee without purchasing power, immediately asking them to introduce you to their director can be insulting — and it can have big ramifications down the line.

The gatekeeper doesn’t just hold the keys to the decision-maker’s calendar — they usually also have the buyer’s ear. Even if you get a meeting, you might find that the executive is unhappy about how you treated the gatekeeper.

“If you treat them like a professional, treat them as an ally, it’s going to help in the long run.”

Given how busy executives can get, booking a meeting in a timely fashion can be difficult, too — especially if the gatekeeper isn’t inclined to help you out.

“So remember that that influence of the gatekeeper is important,” Kelly said. “If you treat them like a professional, treat them as an ally, it’s going to help in the long run.”

Of course, it’s also just the right thing to do.

Tailor Your Pitch to the Gatekeeper

During a sales training exercise at a previous employer, CultureIQ Account Executive Anthony Monroig had the opportunity to ask an executive assistant about what they’re thinking when a sales rep calls. What he learned changed his entire pitch strategy.

“I’m putting them in the same context as the CEO because sometimes they know that calendar better than the CEO.”

The executive assistant told him that she meets with the CEO once a week, and that the CEO shared their top five priorities for the week. It doesn’t matter how dazzling a rep’s pitch is or how charming they are — they’re not getting a meeting unless they fit in with one of those priorities.

Now, when Monroig speaks with an assistant, he takes the time to understand what those priorities are and make sure he pitches to that.

“If I’m speaking to an executive assistant, I’ll let them know, ‘I’m sure there’s maybe two or three things that Mary’s focused on, do you know how culture happens to fit into that box?’” Monroig said. “I’m putting them in the same context as the CEO because sometimes they know that calendar better than the CEO.”

While it’s important to treat the gatekeeper as a partner of the CEO, that doesn’t mean they need the same information. The goal is to give them enough information that they can advocate for you to their executive. Kelly suggests starting with some information about your product, the value it can provide the firm and then a strong argument for why the CEO should get involved.

That can require a little research. Following company earnings reports and media output can help, but Kelly will often call his prospect’s sales line and ask them point blank how he can get on the CEO’s calendar. During those conversations, he’s learned things that might not come up in a report, like the fact that a company just hired three new sales reps.

He’ll then cite that information on his call with the gatekeeper and explain that he has information that can help the CEO ramp those employees quicker.

“If you sound like a salesperson, you smell like a salesperson, and you smell like you’re pitching, they’re going to pitch you to the voicemail,” Kelly said. “You need to personalize your data.”

Turn Them Into an Ally Throughout the Buying Process

The equation changes when the gatekeeper is an employee who has authority but not purchasing power.

At Displayr, Mudawar sells to marketing directors at Fortune 100 companies. Since it can be difficult to reach them, she’ll often need to get the buy-in from marketing analysts further down the company ladder. At this level, her goal is to turn the analyst into a champion for the product, since they may have a bigger role in the buying process.

To do that, she tries to target the analysts she thinks will be most likely to advocate for her product. She’ll research LinkedIn accounts to find a few employees whose job descriptions relate to her product and who have previously worked for companies that used Displayr.

“I try to explain it and make sure people realize this is an opportunity for you to level up your career.”

Her pitch then focuses on how the product can help them personally. This is where customer stories can help, Mudawar said. Since her company is automating a portion of the analyst’s job, she’ll often come across gatekeepers afraid it will put them out of work. Explaining to them how the product has helped other employees move into higher-impact roles is a quick way to help them see why they should advocate for the tool.

“I try to explain it and make sure people realize this is an opportunity for you to level up your career,” Mudawar said. “Customer stories are super powerful.”

If an employee is on board, she’ll encourage them to arrange a team product demo as a next step. This helps her get more employees on board and keeps the buying process moving.

This strategy has helped Mudawar find analysts who were willing to champion her cause throughout the buying process.

“Not only that — they then helped us expand out to other groups internally and spread the word with referrals to other businesses,” Mudawar said. “Those are the best examples where there’s someone who other people might underestimate [...] and they open so many doors for you.”

Create a Cadence for Gatekeeper Outreach

Winning over a gatekeeper might take more than one conversation, however. Monroig tries to get in touch with a gatekeeper at least six separate times before he accepts a rejection or tries another strategy.

Those six touch points are important because there’s no telling what kind of day the gatekeeper may have had before he contacts them. They may be rejecting him because they’re slammed with work or because they’re dealing with a personal issue. Over time, those instant rejections will become less common because a relationship has been established, he said.

But his relationship-building doesn’t end there. He also puts the gatekeepers of his top 25 accounts in a separate sales cadence and keeps notes about them. During his calls with them, he’ll share details about his life and ask how they are doing. If the point of contact talks about family, he’ll make a note to check up with them on how their family is doing. And when holidays roll around, he’ll send them a holiday card with a picture of his family.

“They are an incredibly strong asset and tool. You just have to treat them that way.”

Another strategy that can help is to keep the gatekeeper in mind when sending a care package to the CEO, Kelly said. In one instance, he asked the assistant for advice on what to include in a care package for their CEO and then added a Starbucks card for the assistant as well.

Ultimately, taking the time to build those connections pays dividends down the line. When he has a good relationship with a gatekeeper, they’ll often follow up with him after the call to book the next meeting.

“They are an incredibly strong asset and tool,” Monroig added. “You just have to treat them that way.”

Overcoming Rejections

Of course, sales reps can’t sit around forever waiting for gatekeeper approval. And sometimes, a gatekeeper just won’t budge from their initial rejection.

In those cases, it’s important to take the time to fully vet the relationship. After a call with an assistant, Monroig will often send a follow-up email thanking them for their time and asking them to confirm that they received the message. He’ll then give them a few days to reply and then follow up again.

If a couple weeks go by and they still haven’t responded, he’ll then start to work around them.

If the gatekeeper does reject you, it’s important to understand why. Every company will have a budget rejection, so Mudawar will often use that as an opportunity to dig deeper. Asking about what tools they do deploy and understanding why they aren’t in the market for a new tool can yield valuable information for her next outreach cycle.

Armed with new information, she can send messages that address the rejection rather than running to the next person.

“There’s an overall misrepresentation of who those folks are.”

When all else fails, it might be worth trying to go right to the source. To do that, it’s important to take the time to connect with the executive on LinkedIn first and engage with their posts. That way, you don’t come off as a complete stranger, Monroig said.

He then recommends trying to time the call for either 8 a.m. or 6 p.m., when the CEO is least likely to be busy, to make his pitch.

One way or another, however, all roads usually lead back to the gatekeeper when it comes time to book a meeting. Sales reps can either work with them or face roadblock after roadblock in the sales process, Monroig said.

“There’s an overall misrepresentation of who those folks are,” Monroig said. “They’re in tune with the business strategy, they’re in meetings with the CEO. So salespeople need to start looking at them as valuable assets and ways to get to the CEO versus getting around them.”

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