6 minutes
April 8, 2021

How to sell to CEOs & other executives (hint: you don't)

How do you sell to a CEO? It can seem daunting — but the key to s elling to executives is to build a real relationship and provide real value.
Sabrina Jowders
Table of Contents

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Key Takeaways

  • Executives, especially CEO, are unique people — so understand the best communication method for each individual such as short emails over unplanned cold calls.
  • Focus on building a rapport through understanding the CEO’s priorities and interests, often facilitated by connecting with their executive assistants or the COO of the organization.
  • Demonstrate clear value in your communications by addressing the CEO’s specific business needs and priorities, avoiding direct sales pitches in favor of useful queries or insights that are clearly tailored to them and their company.

We hear the question time and time again, "How do you sell to CEOs?"

The answer is, you don't.

CEOs wear many hats and hate wasting time in their hectic schedules. When it comes down to it, their main priorities are their relationships with their investors, customers, and potential customers.

During a webinar called How to Sell to CEOs, Olof Mathé (Co-Founder and CEO of Mixmax), Eric Spett (CEO of Terminus), and Roy Raanani  (Co-Founder and CEO of Chorus) were asked if they had ever purchased something that started with a cold email to them.

All of their answers were no.

As they're not experts in every area, CEOs hire trusted decision-makers at their companies to do this for them. But they all agreed that they're more than happy to get a sales rep in front of the right person if approached the right way.

Believe it or not, CEOs are people like you and me. They have families, binge-watch their favorite TV shows, and they have a life outside work.

Connect with them, get personal, and build trust, just like you would any other prospect. At the same time, keep a few other differentiators in mind.

Tip #1: Know their method of communication (cold email vs. cold calling)

All three CEOs admitted they do not have desk phones (who does anymore?). They won't even answer their cell phones to unknown numbers (just like everyone else, right?).

If you do happen to get through, they might pick up your cold call, you must ensure they will engage with you. Really hard to do with a busy CEO.

What about voicemails, you ask?

"I delete them right away."

"I don't even have my voicemail setup."

Two direct quotes.

Email is probably your best approach. It's essential to remember that these are high-level individuals. Their inboxes are constantly flooded. They are getting emails to try products or services, emails from investors, emails from customers, emails from their employees, and the list goes on.

Also, keep in mind that with an inbox this busy, they will most likely have software that will filter their inbox. You do not want to get sent to spam… so how do you stand out? Two concepts: personalization and building a relationship.

Tip #2: Build an authentic relationship

When you're reaching out to CEOs, some degree of flattery works. You're putting them in a good frame of mind, and let's face it, who doesn't like hearing how awesome they are? But usually when you're doing this, you are personalizing, showing that you have done your research.

Eric, CEO of Terminus, shares, "If someone has put a lot of time into personalizing and has made it really relevant, I at least will read the email. Most of the time, I will forward it to someone who would resonate with it or forward it to our SDR manager/sales team and say, 'this one caught my attention, and here's why"

A significant component of getting a response is providing a personal story on how their product/company has impacted your life in some way. Often, this is a more powerful way to get the attention of a CEO than having a mutual connection. You are showing how you have interacted with the product/company and are now putting in the effort to build a relationship with this individual.

More often than not, CEOs have gatekeepers in the form of their Executive Assistant. Don't dismiss building a relationship with that person.

The Executive Assistant relationship can be the key to building a relationship with the CEO you're trying to prospect. Executive Assistants can pull strings to get you on a call or push the CEO for a meeting they would have never taken.

"If someone has put a lot of time into personalizing and has made it really relevant, I at least will read the email. Most of the time, I will forward it to someone who would resonate with it or forward it to our SDR manager/sales team and say, 'this one caught my attention, and here's why".

Tip #3: Know their priorities & focus on value

The maturity of the company depends on priorities. Companies change constantly. Therefore, CEOs' priorities for their company are continually evolving as well.

As a sales rep, keeping up with the organization and knowing the current state of the business will help you discover a CEO's priorities before you reach out to them and show how you can provide value for them. You don't want to waste their time otherwise.

Even if you are not showcasing what they may need right now, you may be what they're looking for in 8 months. If you've built enough of a relationship with them, you'll always be in the back of their mind when the time makes sense to have that discussion.

If all else fails, a general theme is that CEOs care about their relationships with their investors, customers, and potential customers. They want a fantastic customer experience, so relate back on how your product/service to how you can contribute to a great customer experience, and you'll probably attract their attention.

Before you send that email, ask yourself, "have I proven how I can provide value to their priorities? Why would they respond to this email?".

Tip #4: Ask simple (but smart) questions

Never ask a CEO to hop on a call with you or if you can schedule a time for a meeting. They will never take you up on that offer. These people are busy and hate wasting time. Why would they spend time taking a meeting with someone they barely know?

Roy, CEO of Chorus said, "If you ask for money, you'll get advice. If you ask for advice, you'll get money." If you are cold emailing a CEO and directly asking them to hop on a call, they will reply (if they even take the time to) with feedback on what you should have said to save the time and effort for the next person.

The best approach is to ask a simple question that is worth their time and will take minimal effort to respond to. Roy shared a story of a cold call gone wrong, and his feedback for the rep was, "If you had asked me a single question, 'Do you know what percentage of emails your sales team is sending that are highly personalized and end up bouncing? This will impact and help you grow, I would think, 'no, I don't know this number," and then I would meet with my VP of Sales and ask him this question, and then when you follow up with me, we can then discuss the opportunity and value you provided me."  

Adjust your messaging, and resonate with the prospect more. Put yourself in their shoes and know what their day is like and what their priorities are.

Summary: don't focus on selling to CEOs and other executives

When three CEOs were asked if they had ever purchased something that started with a cold email, all of them answered no.

The key takeaway is that these CEOs always passed purchasing decisions off to those they put in charge of particular concerns or departments. While they may be the final signature needed to make a purchase, CEOs trust their department leaders to make decisions themselves.

Instead of looking at CEOs as the ones with the wallets, focus on building relationships with them, and they can open doors for you.

The best way to approach a CEO is to understand their methods of communication, build trust over time, know their priorities, and leave them with simple questions that prove you can help them and provide value. Don't pitch to them or push for a meeting.

At the end of the day, remember that CEOs are people, just like you and me.