Selling to Executives? 3 Types You’ll Meet & How to Handle Them

Certain challenges come with selling to executives. These prospects can be difficult to reach and tend to pack their schedules well in advance. The good news? Finding out early in the outreach process both who you’re dealing with and what their preferences are can help to optimize prospecting attempts with these folks. In other words, if you figure out whether a prospect falls within a certain character type, you can tailor your outreach from there.

In my experience, many executives fall into one of three personas (affectionately named below). Let me introduce you to…

1. The “Bill Murray” Executive 


Bill Murray
Photo credit: CVT Soft Serve

Bill Murray’s been seen on social media taking random pictures with surprised fans everywhere — from posing in ice cream shops, to even crashing wedding photos. He’s the kind of guy that will apparently show up when you least expect it and be more than willing to make you laugh.

There are executives who do this, as well. Just when you think it’s going to be impossible to reach them… BAM on the first call they answer, ready to talk. This type genuinely likes making connections and makes themselves easy to reach. That said, they are often hard to close. With all of the calls they take and pitches they receive, these executives are inundated with things to do. You have to hook them on the first call and get them to move quickly. If you don’t, they can lose interest quickly and get pulled in other directions.

The best way to contact?

  • Just call them!

Things that could suggest they are a “Bill Murray” Executive:

  • Receptionist gives you a direct extension or cell phone number right away.
  • They list their phone number on their LinkedIn page on the company website.
  • Assistant will transfer you without too much questioning.


2. The “Mark Cuban” Executive

Mark Cuban has made a name for himself in the last decade for being the prototypical businessman. He’s extremely passionate about making his businesses succeed, but with this passion also comes careful consideration; Cuban picks and chooses who he makes a connection with.

This is the most common type of executive, accounting for about 50 to 75% of everyone that you will contact. They rarely answer a call from an unknown number, but will reply to an email or voicemail if they find value in what you say. If you don’t articulate your value, they won’t hesitate to press delete.

The best way to contact?

  • A great voicemail, email or LinkedIn message. They often won’t respond the first time you reach out, but will return emails or answer calls once they decide you are someone worth talking to.

Things that could suggest they are a “Mark Cuban” Executive:

  • They’re listed in the company directory.
  • The company website provides their email address.
  • Their phone actually rings when you call.
  • They have an updated LinkedIn profile and are active on social media.
  • Their receptionist/assistant will ask who you are, but will still be open to transferring you.


3. The “Michael Jordan” Executive

Michael Jordan is a difficult person to connect with. Rumor has it that he doesn’t sign autographs, never takes pictures and doesn’t like making public appearances. The guy really just wants to be left alone — just like some executives.

In my experience, it’s best to learn how to identify a “Michael Jordan” executive right away, so you can prospect carefully. It often takes some extra creativity to get in front of these folks. For example, try to get in touch with someone else at the company who has influence over the “Jordan” and get them to help you make the connection. You can also attempt to reach out to this executive via LinkedIn, but make sure to start by mentioning shared connections, which can be helpful in establishing some credibility.

The best way to contact?

  • Reach out to an influencer and have them help.
  • Attempt through LinkedIn, mentioning shared connections.

Things that could suggest they are a
“Jordan” Executive:

  • Their voicemail is always full.
  • They are not listed in the company directory.
  • Their receptionist/assistant questions you hard when you call.
  • Their phone never rings and goes right to voicemail.
  • Voicemail has a default “robot” type of greeting.

Ideally, you’d be able to fill your prospecting list with all Bill Murray and Marc Cuban executives and eliminate calling the Michael Jordan types after a few attempts. Realistically, though, you’ll come across some Jordans and need to go after them. Accept it as a challenge, and then celebrate a little longer when those prospects become a sales win.


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