When I started in sales, my only job was to make cold calls: usually 100 a day, targeting high-ranking company leaders whenever possible. I always knew executives were the most important people to speak with; I didn’t realize how daunting it can be until it was my responsibility to get them on the phone.

At first, I was terrified – how could I, a recent college grad, have a reasonable business conversation with an experienced and powerful CEO, or CRO? I wanted to skip those names on my list so badly, but I dutifully persisted and instead - just hoped they didn’t pick up.

After gaining some confidence and developing better messaging, I started to look for creative ways to reach these busy executives, who rarely answer the phone. This became a fun challenge, and it was exciting to see my success rate climb.

Then, I discovered something unexpected. For the most part, C-Level prospects are easy to talk to! Most salespeople are afraid (like I was) to call C-Level prospects, or doubt that they will pick up. This means it’s rare for someone in the C-Suite to talk to sellers. As a result, executives are often more receptive than you may anticipate. Often enough, executives are appreciative of the skill it takes to reach them, and will entertain what you have to say if you manage to open up the conversation.

I don’t think my experience is that unique. Many sales teams hesitate when reaching out to the C-Suite, and with good reason—executives know more about their business, industry and needs more than any sales person. Sellers might also feel that attempting to reach the executive is a waste of time because they rarely engage. To get past this wall, sales people need to be very deliberate about their process for getting through and conveying a good message.


Reaching the C-Level

Most executives at a high level have support staff of some kind. Their primary administrative assistant is a good person to know and speak with. In today’s world, the C-Suite is not in the office every day. They travel often, work remotely and squeeze in vacation too. Assistants can be helpful in sharing the schedule or routine of their bosses. You might consider putting them on a special call list so you can take a different approach to reaching them. I had the most success reaching people while they were driving home, around 6pm. Sometimes you’ll encounter an admin who manages your prospect’s voicemail and email – they’ll intercept anything you send. What they rarely manage is the LinkedIn or Twitter account of your prospect. These channels can be a great way to get the attention of a C-Level executive; just remember to focus the message on them and your interest in what they are working on, THEN follow up with why you should connect or continue the conversation.


Conversing with the C-Level

Talking points that have been successful with your Director and VP prospects will likely fall flat with a higher-level executive. Day-to-day challenges and problems are for their direct reports; executives look at the big picture. For this reason, dwelling on any attractive benefits or features of your product won’t mean anything to executives. Effective talking points come from referencing how a small challenge might develop into a more pressing need. Imagine your C-Level prospect sitting in a room with their peers and the Board, explaining why the results of the last quarter did not go to plan. This is the moment that executives are preparing for, and messaging around that focus will have the most impact. Leverage the fact that C-Level targets think further into the future and aim to insulate themselves from the unexpected.

When selling to the C-Suite, confidence comes through successful repetitions. Focusing on these two areas of interaction will improve your success rate and help you develop a greater comfort with the highest level of decision makers.

Increase sales with the C-Level.


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Selling to the C-Suite

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