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C-Suite Selling: 5 Surprising Strategies for Selling to Executives
Shawn Casemore - Accelerate Sales Growth Shawn Casemore - Accelerate Sales Growth
For Immediate Release:
Dateline: Toronto, Ontario
Wednesday, December 14, 2022


Are you selling to the C-suite?

  • Have you found it’s difficult to get the attention of these folks that are executives, busy executives at that?
  • Or maybe you’re finding that you’re connecting and you’ve got something that’s working, but you want to know if it could work better.
  • Or, you want to connect with more executives for more selling opportunities?

In this video,  I’m going to cover the strategies you need to incorporate for C-suite selling and break down those barriers that are delaying or holding back on some of your sales opportunities.

5 Strategies for Selling to C-Level Executives

Whether you’re new to sales or maybe you’ve been in sales for a while, you’ve likely found that dealing with

  • getting the attention of,
  • getting meetings with, and
  • selling to C-suite executives

is a little bit challenging.

Who are C-Level Customers?

By C-Suite, I mean CFO and CEO, and even at the VP level.

These executives are very busy and they’re often fighting multiple fires at any one time and dealing with multiple priorities. Their job is overwhelming for the average person in many cases.

To be honest with you, I’ve been there. I know! You might have the same experience.

5 Strategies for Selling to Executives

What we really have to consider is this:

The way we approach and get the attention of C-level decision makers is a little bit different than our approach with a manager or a director, or even an individual business owner.

Let’s jump into some of these key strategies I want you to use, and some of which are either going to be scary or catch you off guard, but they work.

So let’s get into number one.

1. Be Provocative

The first point for you is going to seem a little bit counterintuitive. But, you need to be provocative.

The goal here (with executives who are so busy) is that

  • we have to say stuff that others aren’t saying,
  • we have to catch them off guard, and
  • we want them to go, “What the heck do they mean by that?”

That’s being provocative.

What are some examples of being provocative in sales?

Be Provocative

Instead of reaching out and trying to have a meeting to talk about the value and benefits of your product, you might reach out and say:

“You know what? I was thinking we should meet a year from now because for my estimation, that’ll be a good time for you based on when I estimate your product may need replacement.”

At this point most buyers would think, “What does he mean? Meet a year from now? Why is he calling me now?

And you see, it’s that response that we’re going for.

We want them to think, “What is he talking about?”

Or, you might be at a meeting or a networking event and you introduce yourself to somebody:

“Hi, I’m Shawn. I sell XYZ.”

And they say, “Oh, nice to meet you.” (And you can kind of tell they’re thinking, oh yeah, here’s Shawn. This guy’s gonna try and sell me something.)

And you could even say to them in that moment, being provocative. “Say, you know what? I’m hoping that we never have to have a sales conversation.”

They’re gonna say, “What? You’re in sales!

Now, the key to being provocative is you have to be able to back that up with something. So you wanna make a statement that gets them to go, “What?

But, you have to be able to respond with something that’s not a lie. It’s honest. You’re just simply twisting the words around a bit to get their attention.

So let’s run a role play then on that last point:

I might say to you, “You know what? I hope we never have to have a sales conversation.

They’ll probably laugh and go, “Me neither, but why would you say that? Aren’t you in sales?”

My response might be, “Oh, I’m in sales. But ultimately I’m in helping our clients achieve a return on investment that more than triples their investment in our product. And we can usually do that in six months. You know what? If you have a few minutes in the next month or so, why don’t we put something in our calendar?”

You see, I twisted that from a

  • “What?” to a
  • value statement and then into
  • a meeting.

Being provocative opens up the door. We want somebody to say, “What do you mean by that?”, which opens up the door for us to move into our sales process.

Step one, be provocative: Get their attention.

2. Speak in Terms of ROI

The second thing I want you to consider when it comes to dealing with C suite clients is you need to use their language.

Speak in terms of ROI

That is, talk in terms of
  • ROI, “return on investment”, which is money and
  • ROTI, “return on time invested”.

I won’t go into explaining them here, but you can easily look them up.

These calculations really are the way they speak.

  • Executives think about how much money do we have to spend and what do we get in return?
  • They also think about how much time do I or we need to spend, and what is my time savings as a result.

So you need to use these kind of terms and phrase your discussions around these in order to get their attention.

3. Pushback If You Disagree

This third point is about pushback.

C-Suite Selling - Push Back

Now, this is going to feel very uncomfortable if you’re not used to doing this, but trust me, it works.

Executives create their assumptions on different areas of the business and what needs to be invested in, what they need to purchase, and what they don’t. Those assumptions are based on their own experience as well as what their teams are telling them.

But you being the sales professional, you know more than they do about your product or service. You’re the subject matter expert. You faced all sorts of scenarios, all sorts of buyers. So if a buyer is to say something to you that is a little bit out of the norm,

Maybe they say something, you’re like,

“Oh, we don’t think this investment’s really gonna save us any time.”

Don’t say, “Well, yeah, I can understand why you think that way.”

You’ve got to push back and do it using that provocative nature.

You could take a few different approaches in order to push back:

You could ask a question, “Oh, why is it you think that?” (Now that’s not super pushback, but I’m not going, “Mm. Yeah, I understand that.”)

There’s a lot of phrasing and terminology training out there that suggests to agree with what somebody says and then turn it around.  But, that’s not being provocative.

Remember, C-Suite executives don’t have a lot of time.

So, I might want to ask a very direct question:

“Why is it you think that?”

Or, I might want to give them something that pushes back: “Actually, our clients have found they save twice as much time. The sooner they invest, the more savings they achieve.”

Now, again, just like being provocative, I’ve got to be able to back that up with statistics and information.

But the point is, don’t just accept something that a C-suite executive says and just nod and say, “Okay, yes, I understand. No problem.”

You want to push back because all day long they’re dealing with people around them that are telling them “yes”, and “thank you”.

You’ve got to stand out amongst that! And one of the ways is to push back, particularly when they say something that you know or you can back up that is not true.

It’s going to be uncomfortable, but you have to do it. Just make sure you can back it up.

4. Consider Yourself as Their Concierge

C-Suite Selling

If you’re trying to sell to the C-suite, you need to consider yourself a resource for them.

I’m not suggesting you’re there to, to, to bring them coffee and that kind of thing. You need to see yourself as what I call a sales concierge.

Think about it, when you’re in a nice hotel, and they have a concierge service, any issues or problems get directed to the concierge:

  • So you can’t find a parking spot, go talk to a concierge, right?
  • You get a problem with the room, go talk to a concierge.
  • You’re looking for restaurant directions for a nice restaurant for dinner. Go talk to the concierge.

You need to see yourself in that manner.

A recent study by LinkedIn showed that 88% of buyers in the B2B space specifically end up buying from those who they see as trusted advisors.

Trusted advisors are concierge. They’re people that are there to help.

So just because I’m selling you product A doesn’t mean I can’t give you ideas and feedback in other areas that I might have experience in.

You’ve worked for other companies. You may be not pitching their product or service, but I might point out,

“You know, there’s a better solution to racking those products out there. I’m not sure if you’re aware of it. Or, you know what? It looks to me, by looking at your financials, that your cost for insurance is high.

I’m sure it’s a great company, but there’s others I’m happy to introduce you to that I know have lower rates.”

I might not be selling insurance services, but by giving ideas feedback, I’m starting to create this idea that I’m a concierge. What I’m doing for that C-Suite executive is creating the need for me.

They need me, then they’re going to need to buy my product or service.

So I want to make myself that resource by acting as a concierge.

5. Stay Connected

This last tip is a little bit outside of what we’re talking about here, but it’s important for you as a sales professional.

Selling to the C-Suite - Stay Connected

C-suite executives move around a lot. They’ll take different executive roles in different companies.

So whatever you do, whether you sell somebody something or not, always stay in touch. Even though you don’t sell them something at company A, continue to

  • stay in touch,
  • be provocative,
  • push back when it makes sense to do so, and
  • act as a concierge,

because they might move to company B, which offers a whole new opportunity.

Let’s be honest, not all C-suite executives have the full authority to make a buying decision. Sometimes it might have to go to their boss, the CEO, or even the board.

If that’s the case, maybe they didn’t buy from you because the board pushed back.

So, always stay in touch with your C-level contacts as you build these relationships. Never let them go.

They’re going to offer you new opportunities to sell when they move to new companies.

Next Steps for C-Suite Selling:

Plan Your Activities with My Sales Planner

As a sales professional and somebody who’s selling into the C-Suite, you really have to be clear on what you’re doing and when you’re doing it.

For that reason, I created what I call my 30-Day Sales Action Planner.

You can print it off, or you can use it electronically. It really lays out your week and the specific activities you need to focus on.

It’s my gift to you. Click the link, and grab yours right now.

Watch Related Video

Now, if you’ve been selling to C-Suite executives, the next video I want you to check out is about selling into big companies.

There are some nuances you’ll want to consider, and most big companies have C-Suite executives. So these two videos are complementary.

Watch this video next: Selling Into Big Companies.

Until next time, let’s get out there and go sell something!

Thursday Thrive Opt-In

© Shawn Casemore 2022. All Rights Reserved.

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Name: Shawn Casemore
Title: President
Group: Casemore and Co Incorporated
Dateline: Chatsworth, ON Canada
Direct Phone: (519) 379-7697
Main Phone: (519) 379-7697
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