How to Get Past the Gatekeeper, According to Sales Reps

Tarzan and Clayton.

Simba and Uncle Scar.  

Sales development representatives and gatekeepers.  

All tales as old as time.

If you're in sales, chances are you've encountered plenty of situations in which you're trying to reach a CEO or C-level executive to pitch your product or service ... only to get stopped by a gatekeeper.

Gatekeepers — who are typically executive assistants, receptionists, or office managers — are the people who stand between you and the decision-maker with whom you're hoping to make a sale.

But experienced sales reps know that gatekeepers don't have to be a roadblock in your sales process. Instead, a gatekeeper can (and should) be used as an opportunity to win the prospect's trust.

Here, I spoke with 13 sales reps to collect a list of tips you can use next time you find yourself up against a gatekeeper. Let's dive in.

How to Get Past the Gatekeeper When Cold Calling

1. Treat the gatekeeper as a resource, not an obstacle.

HubSpot Account Executive Chrissy Callen told me she considers gatekeepers less an obstacle, and more a resource when trying to reach a decision-maker.

As Callen says, "If it's a receptionist or an assistant, they hold so much power in what the decision-maker's day-to-day looks like — so lean into that. If they aren't in a rush to get off the phone, take some time to ask how their day is going and get to know them."

It might seem simple, but treating the gatekeeper as a human is an important tactic when trying to reach executives. And it's the right thing to do, too.

Callen adds, "I find when you do this, gatekeepers will usually open up a bit more, and are more willing to give information as to when you should call back or the best way to reach the decision-maker."

2. Name-drop a connection.

Andrew Dickelman, Co-Founder and Head of Enterprise Sales at Structurely, has been responsible for millions in revenue through cold outreach. As a result, he's refined two strategies that work well when getting past a gatekeeper.  

First, he suggests, "Name-drop someone they're likely to know (e.g. someone in their sphere/market, or someone who works for a bigger brand name). When met with gatekeepers and using this approach, I'd say something like 'Oh, I've been working with John Doe in your market, who [decision-maker] knows. He wanted me to connect — can you put me through to help make that happen?'"

Alternatively, if you don't have a strong connection to the decision-maker, consider how you might name-drop a publication related to their work.

As Dickelman advises, you might say something like, "'I've been reading/listening/watching some of [decision-maker's] recent work, and as a speaker in multiple industry publications myself, I'd like to connect to discuss these topics further. Can I speak to them about that now, please?'"

It doesn't hurt to do your research. The more you know about the decision-maker, the easier it is to connect on a personal level with the gatekeeper and demonstrate you're not just another cold caller.

3. Be polite and exude confidence.

QuotaPath Senior Account Executive Alex Brennen told me it's critical sales reps remain polite and exude confidence when speaking with a gatekeeper.

She says, "Something small but impactful is to always say your first and last name. This establishes trust and shows you have nothing to hide."

It might sound simple, but in practice, it's a little more challenging. Perhaps it's the end of the month and you haven't hit quota yet. As a result, you might come across as exasperated or frustrated when speaking with a gatekeeper. But that's not what you want.

Instead, ensure you sound respectful and courteous. It's not fair to convey your stress to the gatekeeper — they're just doing their jobs, too.

4. Don't use the decision-maker's last name. 

Mark Smith, a BDR at Proposify, believes the key to getting past the gatekeeper is sounding confident over the phone. Additionally, he told me he's found success by asking for the decision-maker by first name only. 

As Smith puts it, "My usual phrasing is 'Is [decision-maker] in the office today?' or 'Is [decision-maker] around?' When doing this, never use the person's full name. I repeat ... never use the person's full name! If you're talking to a friend, would you address your friend by first and last name? No."

Smith adds, "If they ask for the last name, of course you should give it, but never lead by addressing your prospect by their full name."

5. Don't lie. 

One thing that could break the gatekeeper's trust — and ruin the success of a deal? Dishonesty.

Whatever you do, you don't want to lie to get past the gatekeeper.

As Damian Schlereth, Business Development Manager at Qwilr, told me, "When interacting with a gatekeeper, there is one rule I enforce with our BDR's: don’t lie. Align the call with your email cadence content — lead with the truth and be firm but humble in your approach." 

"For instance," Schlereth adds, "You might say, 'Sarah, I'm hoping you can help me. I am supposed to be connecting with John Smith today but can't find his extension/we haven't been able to connect yet. Could you patch me through, please?' Be very polite, and acknowledge their help."

Ultimately, even if a lie might work in the short-term, it's likely it could backfire in the long-run. If your decision-maker finds out you've lied to her employees to reach her, she won't want to do business with you. If you lied about that, what else might you be lying about? 

6. Have some background knowledge about the gatekeeper. 

Cam Karosis, a HubSpot Growth Specialist, advises sales reps to do their research on the gatekeeper. 

He says, "If you know who your gatekeeper is ahead of time, check out their LinkedIn. If the gatekeeper is slightly higher up and might be someone who's used software similar to yours in the past, look up their prior companies and see what tech they're using."

Karosis adds, "This might trigger memories of negative experiences in the past with software they weren't fond of, or positive experiences with your software, etc., that you can bring up on the call and show that you've done your research and you're not there to waste their time."

7. Don't try and 'get past' gatekeepers … align with them.

Finally, when you cold call a business and reach a gatekeeper, consider how you might create rapport and build trust with the gatekeeper before you push for the C-level executive.

As HubSpot Account Executive Carl Ferreira told me, "Gatekeepers are humans and they are charged with protecting the time of their executives. So if you are a time-waster … unfortunately you will not get past the gatekeeper and will have to resort to pushy, sales-y tactics to bypass the gatekeeper."

However, Ferreira adds, "Gatekeepers can be extremely valuable if you win them and align with them as opposed to 'getting around' or 'bypassing' them. This is one area where a modern seller can differentiate from a legacy seller."

That's all well and good. But how do you align with the gatekeeper?

Ferreira tells me, "Don't treat them like a gatekeeper. That dehumanizes them. Treat them like you would treat the CEO you are trying to reach. After all … that CEO trusts and likely has a close relationship with that 'gatekeeper' already."

How to Get Past the Gatekeeper in Medical Sales

You can implement some of the strategies listed above if you're in medical sales and you're trying to get past a gatekeeper — however, there are some additional challenges you'll come across in medical sales. 

Within the medical sales industry, you'll want to build an internal network so you can leverage industry contacts.

To build a network, spend some time in the field — for instance, perhaps you do marketing for a medical office, customer service in a hospital, or even vending sales in a hospital setting. 

These field experiences enable you to build expertise and a strong network of medical professionals.

Then, when you're ready to sell to decision-makers in the medical industry, you should have internal contacts you can leverage when calling a gatekeeper, such as, "Dr. Henry told me your hospital doesn't have X technology, which could help your staff save time and become more efficient. She suggested I reach out to [decision-maker] ... Mind putting me through?" 

Samantha Agyeman, a Medical Device Sales Representative at Lochness Medical Inc., told me befriending the gatekeeper is key to accessing decision-makers. 

As she says, "You always [want to] befriend the gatekeeper and ask for their names. Also, ask how they're doing — no one ever asks the gatekeeper that. They are usually just transferring people when they call or keeping sales people out."

Agyeman told me she also tries to build relationships with the staff at-large. "Another thing that helps, too, is befriended the staff of your decision-makers because if the staff likes you and what you have to offer, you set yourself up for the most success in front of the decision-maker."

Now that we've covered how to get past the gatekeeper, let's look at some specific examples of what to say to get past one. 

What to Say to Get Past the Gatekeeper

1. Tell the gatekeeper you have a connection at the company.

Brennen told me, "While all good sellers will have their own techniques when cold calling, here are a few of my go-to's — first, try leveraging if you've had a response with another contact there."

Brennen adds, "This could look something like, 'I was speaking with Wilson and they pointed me in the direction of Jeanne. Could you let Jeanne know I'm on hold?' This makes it less uncomfortable for the gatekeeper when asking Jeanne."

Another option, Brennen says, is to email the decision-maker first. "This way," she says, "when the gatekeeper asks if they are expecting your call, you can say, 'I told her I was going to follow-up on an email earlier. Would you mind telling her I'm on hold?'"

2. Explain why you're trying to help.  

Callen told me it's vital you work on gaining the gatekeeper's trust first — and to do that, you want to be open and honest about your intentions.

It's equally important, however, not to sell to the gatekeeper. "They most likely aren't interested in a pitch," Callen says. "Instead, they're more interested in why you're trying to help. You might say something like, 'I'm sure you know how busy [decision-maker] gets with XYZ … That's actually why I'm reaching out — to see if we can help.'"

While you don't want to launch into a pitch when the gatekeeper questions your intentions, you do want to remain honest and transparent about what you're hoping to achieve. Express your desire to make the decision-maker's life a little easier, and provide some basic background information so the gatekeeper has a better sense of who you are.

3. Say 'yes' or 'maybe' when the gatekeeper asks if the decision-maker knows your calling. 

HubSpot Sales Director Dan Tyre told me he thinks of gatekeepers as gate-openers, and has a strategy that has helped him reach the decision-maker in the past. 

First, when Tyre calls the gatekeeper, he asks for the gatekeeper's name and tries to remember it. "That's right, ask them and greet them with their name. 'Excuse me, what is your name? Victoria? Hello Victoria, It is very nice to meet you, thanks for picking up the phone.' Is that so hard? It goes a long way."

Additionally, after he asks for the decision-maker (by first name only), he encourages reps to anticipate the next question. 

"'Victoria typically asks, 'Does Sharon know why you're calling?' If they downloaded a form, the answer is yes ... If they didn't download a form or have a trigger event, the answer is maybe," He told me. "That may be a bit weird, but it is true and it is distinctive, polite, and accurate."

4. Employ humor to build rapport with the gatekeeper.

Sarra Herlich, a sales development representative at PandaDoc, and Joe Huizenga, a sales development team lead at PandaDoc, told me they use a 3-step approach when working with gatekeepers.

Step one: Open with humor.

To use humor in your opening, Sarra and Joe suggest something like — "Hey, I'm trying to find [insert first name] but I guess I don't know how to properly use my dang phone."

Step two: Give them a question with which they want to help.

Next, Sarra and Joe told me they'll use the following question to encourage collaboration between the sales rep and the gatekeeper: "I'm trying to find out who is in charge of X, Y, Z. Would that be [insert name] or someone else?"

Step three: Get the extension before hanging up.

To close out your conversation, Sarra and Joe say it's important to get an extension. Try saying something like, "Before you transfer me, can you give me the extension so I don't have to bother you again?"

Overall," Sarra and Joe advise, "we try our best to acknowledge the gatekeeper as a hardworking person who deserves respect, and a good laugh."

5. Ask the gatekeeper for information. 

Gabby Furlotte, a team lead and BDR at Proposify, told me that gatekeepers typically hold a lot of information. 

Furlotte says, "If they give you the typical 'they're busy, they aren't interested' response, use this: 'Thank you, I appreciate you taking my call. I'm looking to get in touch with the person who oversees the XYZ process here. Is this something you have insight into?'"

"They might actually end up directing you to another person," Furlotte adds, "or if they know a little bit about what you're calling about, they might be willing to give you some information."

6. Do your research to understand each stakeholder's agenda. 

Steve Findley, Senior Account Executive at Qwilr, advises, "Do your homework first. Know who the decision-maker is, but also identify other influencers and company contacts that might be easier to reach."

Additionally, Findley told me it's critical sales reps take the time to understand the agenda of each individual stakeholder who might be involved in a deal. This information can help you get past the gatekeeper, and will also serve you well when making your pitch. 

As Findley told me, "Map out the company hierarchy as you understand it, and tailor your pitch according to the objectives of each stakeholder."

Findley provided two examples — one, when speaking with a CFO or financial stakeholder, you'll want to talk in terms of financial ROI. Alternatively, when speaking with a team leader, you might leverage the efficiency or time savings of your solution.

Once you've done your homework, Findley advises saying something along these lines to the gatekeeper: "'Dave Smith in Marketing mentioned this project would deliver X,Y, Z, and suggested I reach out to Bob directly to get his feedback.'"

7. If need be, leave a voicemail for the decision-maker ... and then call back later. 

Tyre told me if he can't get in touch with a decision-maker, he always says yes when a gatekeeper asks if he wants to leave a voicemail. 

"And then you leave a 20-second, professional, focused voicemail that shows you did research and are interested in helping," Tyre says. 

Next, he advises reps to tell the gatekeeper, "I am trying to get in touch with Sharon about [business purpose] so I have to call and email four times over the next two weeks to be professional. Do you want me to cc' you on the email?" Asking the gatekeeper if they want to be included on the email chain earns trust with the gatekeeper. 

Finally, Tyre tells me he waits two days and then calls back again. But before he calls back, he always does some research on the gatekeeper. "This way, on the second connect call, you can say, 'Wait, are you a History major at McGill?' This helps build rapport and trust."

"Then," Tyre adds, "you can ask — "'Do you know if Sharon got my message/email?' 'Can I leave another voicemail?' Or 'Is there a better time for me to connect with her when she might be available?'"

Finally, Tyre tells me he ends the conversation by asking the gatekeeper if there's anything he can do for them.

Ultimately, building trust and creating a relationship with the gatekeeper is your biggest key to getting past them. 

Getting Past the Gatekeeper Examples

Let's dive into a few examples of sales reps getting past gatekeepers, so you can see how this looks in-action. These are fictitious examples, but they're based on sales reps true experiences.

1. Account Executive Sarah and Gatekeeper Dave

Account Executive Sarah has done her research — she has background information about the decision-maker, Jennifer, including her unique challenges as CEO of her company, Blue Goat.

She also knows Blue Goat just launched a new product, and she suspects they're struggling to keep up with demand. Fortunately, the sales enablement product Sarah sells can help.

Sarah has also done her research and found a mutual connection with the decision-maker: Mark, who is CFO. Mark is a fellow alum of Sarah's college, so Sarah emails Mark and explains that she truly believes her product could help Mark's company as they scale (only after mentioning the college connection).

Mark thanks her for the information but tells her he's not the right person to reach out to — Jennifer is.

Now, Sarah calls Jennifer's office.

Dave, her receptionist, answers the phone. "Can I ask who's calling, please?"

"Hi there," Sarah's voice is confident and respectful. "I'm Sarah Hastings, an Account Executive at Rev. I'm hoping to speak with Jennifer ..."

Unfortunately, Dave cuts her off — "Sorry, Jennifer's not interested."

This doesn't deter Sarah, as she's prepared for this. She continues, "I completely understand. However, I spoke with Mark, and he suggested I reach out to Jennifer to explain how our product will help your sales team work more efficiently. I'm reaching out per Mark's referral."

A pause, and then, "Okay, I'll put you through."

Why This Works

Once Dave understands that someone internally referred Sarah, he can feel more comfortable allowing Sarah to share her pitch with Jennifer. Plus, Sarah focuses on how her product can help Blue Goat grow their business, rather than what she's hoping to get out of the deal – and, best of all, she speaks to Dave with respect and kindness.

2. Sales Rep Elijah and Gatekeeper Martina

Sales rep Elijah spends an hour researching a Boston-based startup before giving the decision-maker, Pam, a call. He learns they've recently received funding, and they've doubled their customers within a six month period.

While he doesn't have a personal connection at this company, he believes his research will help get his foot in the door, particularly since his product is such a good fit for the startup's needs.

He's ready to call.

Martina, the office manager, answers and says, "Hello?"

She sounds friendly, so Elijah chooses the conversational route: "Hi there. I'm Elijah. Who's this?"

"I'm Martina, the office manager at Quick," the woman replies.

"How's your day going, Martina?" Elijah asks.

Martina tells him it's been good, if not a little busy. They chat for a few moments about the warm Boston weather — where they're both located.

Then, Elijah says, "The reason I'm calling is because I've noticed your startup has begun to grow, and quickly. Congratulations, by the way, on the recent round of funding. In my experience I've seen startups struggle with their social media presence as they scale, and I'm hoping I can chat with Pam to explain how we can help."  

Martina tells him Pam is in a meeting, so instead, she sets up a time for Elijah to call back.

Why This Works

Elijah is friendly and respectful. He treats Martina like a human, and he also shows Martina that he's done his research and is not pitching a product or service that won't apply to their company.

Try Alternative Methods

When all else fails, you might consider shifting your methods for getting past the gatekeeper at all. 

Rather than cold calling decision-makers, consider how you might demonstrate value upfront — for instance, Karosis told me that he's found video messaging to be an effective way to appeal directly to the decision-maker. 

As he puts it, "I've found that personal messaging, namely video messaging, almost always opens up that gate."

If you're interested in testing out video messaging for yourself, take a look at How the HubSpot Sales Team Used Video to Engage More Prospects. 

Ed Calnan, CRO and Co-founder of Seismic, agrees that creating high-quality content is a good alternative to cold-calling your gatekeeper. 

“To reach decision-makers," Calnan told me, "companies must make sure that email content is great. 87% of business buyers say online content impacts vendor selection. We're moving from 'Content is King' to 'Experience is King', with today's customers expecting engaging, interactive experiences over static content."

He adds, "To get past the gatekeepers and to the decision-makers in an organization, sales content must be personal, engaging, and consistent with the ability to reach multiple channels."

Ultimately, sales is all about relationship-building, so consider a conversation with a gatekeeper as another opportunity to engage with someone.

As long as you're polite, honest, confident, and knowledgable about the company, you should find yourself getting past gatekeepers the majority of the time (and having less of a Simba and Scar-like relationship) ... and when you don't, you can always try alternative methods like the ones mentioned above.