The C-level sales conversation: preparing for the win

BY:  Rebecca Herson
June 10, 2021
Updated on January 15, 2023

Table of Contents

Not every sales conversation is the same. Sales people can’t expect to approach a sales call with a mid-level manager, who needs to champion your solution all the way up the hierarchy, in the same way as a call with a C-level (i.e. Chief Marketing Officer, Chief Information Officer, etc. ) decision-maker.

If your sales representatives have the same approach for every prospect, they’re only going to succeed when they get lucky and speak to the prospect who matches their approach. Unless you can reliably divide up your sales teams so that the same person only has to interact with the same type of prospect, you need to make sure that your sales employees have the sales training and experience to be able to adjust their approach and conversations according to their audience.

Dealing with C-suite executives is a whole different ball game for a sales rep who up until now has only spoken with mid-level champions. Quite apart from the apprehension they might feel about talking to a high-powered business leader, your sales employees also need to know what kind of style and approach to use in these conversations.

Account executives tend to be the ones who deal with these high-flying leads, so it’s a good idea to talk to them and get some advice before you head off into the unknown. To help get the ball rolling, we gathered these seven tips for succeeding at a C-level sales conversation.

1. Be persistent – before the sales conversation event starts

The first lesson begins before a sales employee even starts the conversation, and that’s not to feel disheartened if it takes a dozen tries before they get through, or having a meeting scheduled and then rescheduled at the very last second. C-level executives are incredibly busy people. Not only is it rare for them to be at their desk, it’s unusual for them to not be in a meeting or already on another call, so prepare sales teams to call, call, and call again.

It’s rarely worth it to leave a message, or to try to arrange a convenient time to call; you’re not one of the most important items on the prospect’s to-do list. That said, the person you are trying to reach probably has an assistant whose job it is to filter out the unwanted approaches and make time for the valuable ones, so try to identify who that person is, and enlist them to help get you in front of the person you are looking for.

2. Do your research to prepare for the c-level sales conversation

Did we mention that C-suite buyers are busy? Let’s say it again; they’re really busy. That means that they don’t have time for small talk and aren’t interested in forming a relationship with your sales rep. They typically want sellers to get to the point, as quickly as possible.

This is not the time for your salespeople to be asking questions about the company’s struggles or vision for the future – this type of information challenges, KPIs and goals should be gathered ahead of time through the reps’ earlier calls with other members of the team. And this then should color how you speak with the c-level person since you already know their hot button issues.

During the call, sellers should demonstrate how well they understand the company by using only relevant examples from the prospect’s geographic area and vertical, and illustrating how your solution can address their specific pain points.

Of course it’s always possible to be surprised and have the c-level say “actually, that’s not what I’m losing sleep over at the moment, this other thing is,” so if that happens, be prepared to listen closely and pivot as necessary.

3. Discuss the big picture

CXOs are not paid to obsess over the fine details of how the company works, but to direct the organization as a whole. They want to hear about how your solution will add value to the business and help it reach its big picture goals, not the benefits that your solution brings to a specific set of employees.

It’s important for sales employees to adjust their focus accordingly, and explain in broad strokes how your product or service will help the prospect achieve HIS/HER goals for the company’s future bottom line.

4. Demonstrate support from across the organization

Despite the popular image of the autocratic, bossy CXO who rules the company with an iron fist, most of today’s executives don’t like to force their opinion onto the organization. At least, not the good ones.

They consult with other stakeholders in the company and check other people’s opinion, so they aren’t about to make a unilateral decision about whether or not to go with your solution. Sales reps have better chances of success if they can show that they’ve spoken to other stakeholders and have champions in different departments.

5. Stand your ground

CXOs may not be autocratic and bossy, but they are (usually) dominant personalities and most of them have healthy egos, too. They’ve generally had to be more than a bit pushy and assertive to get where they are today, so prepare sales representatives to defend your proposition.

Many C-level executives will give sales agents a hard time, ask awkward questions about the weakest points in your product, and challenge every claim you make. Sales employees need to know how to respond in a confident but non-aggressive way to this kind of prospect, because if they back down or get angry, they’ll lose their chance to make a sale.

6. Earn trust with the c-level suite

One of the worst things that a sales employee could do on a call with a C-level buyer is to assume that they’ll buy from you just because of your brand reputation. In fact, it’s best to assume that they know nothing about you. The sales employee has to earn every inch of trust.

The best way to do that is by demonstrating their knowledge of the prospect’s company, industry, market, challenges, and external concerns, and showing they have this knowledge as early as possible in the call.

Sales teams need to bear in mind that the typical C-suite buyer is completely hardened to sales talk. The more impressive the claims, the more skeptical the executive prospect is likely to be, so it’s important for sales employees to know that they have to avoid the temptation to exaggerate their sales pitch, and be ready to back up every single claim with hard facts.

Finally, sales employees shouldn’t push too hard on their first call. They should show their knowledge, state their case, and answer questions, and then allow the prospect time to think it over. It’s a bad idea to press for a decision too soon.

7. Demonstrate that your company is a good, long-term partner

Successful C-level executives typically take the long term view of their company, and are looking for vendors that will stay with them for the long term.

No matter how much their company what you are selling, and even if you are offering the best price, the deal could fall through if they don’t feel that your company will be in it for the long haul.

Long-term vendors are in a committed relationship with their clients, providing service, consulting on issues that come up, and facing up to it if things go wrong along the way. Both parties need to feel there’s something in it for them, and should approach each other with trust, transparency and respect.

The right sales training equips sales reps for every eventuality

As you can see, succeeding on a C-level sales conversation takes slightly different skills and tactics to completing a call with mid-level leads. Offering sales employees ongoing sales training and the opportunity to practice sales pitches in different circumstances helps them build the capability and the confidence to knock CXO pitches out of the park.

Second Nature’s sales training software gives your salespeople the chance to practice their C-Suite sales conversations as often as they want and get immediate feedback and a chance to improve.. Learn how Second Nature can help better prepare your sales team.

Subscribe to our Newsletter

    MEDDPICC, SPIN, or BANT? The right sales technique fo...

    Read More »

    Enhancing Call Center Agent Productivity: 4 Ways AI T...

    Read More »

About the author

Rebecca Herson

Rebecca is head of marketing at Second Nature.

We’re Hiring

We have positions available in our Tel-Aviv and New York offices and remote/hybrid.

Check Our Open Positions

April 16, 2024

BANT’s simplicity makes it an effective part of lead qualification, so sales reps can assess...

September 05, 2023

Sales professionals know that different types of products/services, companies with different values, and different types...

July 31, 2023

It might feel like you’ve only just finished SKO 2023, but it’s not too early...

See Second Nature for Yourself


Compliance & Certifications

With over 50K happy trainees

Welcome to the Experience

Get a taste of various experiences, it take 3 minutes