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Selling to the C-Suite: Basics and Best Practices

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November 23rd, 2023

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Selling to C-level executives can be equal parts daunting and exciting. 

On the one hand, pitching products and services to the leaders in a business can be intimidating. On the other hand, connecting directly with the C-Suite means you can bypass a number of gatekeepers and hurdles that can extend the sales cycle, and make it harder to close deals. 

Gaining buy-in from a C-Suite executive often means you can move a deal through the pipeline much faster, increasing revenue rapidly. However, capturing and keeping the attention of a C-level executive, and tailoring your pitch to suit their needs can be complex. 

Here’s your introductory guide to selling to the C-Suite. 

What is Selling to the C-Suite? The Nuances of C-Suite Sales

Selling to the C-Suite is different to pitching products and services to other employees in a business. C-level executives are the people who work in the highest (most authoritative) positions in the company. They get their name from the use of “Chief” in their titles. For instance, common C-level executives include Chief Financial Officers, or Chief Technology Officers. 

While a C-level professional might just seem like another prospect at first (albeit with more clout), C-level selling can be quite complex. In common sales situations, where you’re connecting with lower-level employees and individuals, you might be able to generate engagement just with a generic pitch about the benefits of your product or service. 

However, C-level executives are only interested in hearing personalized pitches that appeal to their decision-making motivations. For instance, C-level executives want to hear how your product or service will improve their profitability, revenue, employee productivity, and margins. 

This means you often need to invest more time into research, building rapport with C-level executives, and personalizing your pitch to their specific needs. What’s more, since C-levels have significant demands on their time, you need to make an impact quickly. 

The Basics of Selling to the C-Suite: Getting Started

Selling to the C-Suite can be complex for a number of reasons. Not only does it require salespeople to hone a number of hard and soft skills, from social selling to rapport building, but it also requires a careful strategy. Remember, executives are often very busy, and guard their time carefully. 

To ensure you’re getting started on the right foot, you’ll need to:

  1. Identify the Right Decision Maker

First, you need to ensure you’re connecting with the correct executive for your sales strategy. Going straight to the top and asking for a meeting with the CEO or CFO of a company might seem like a time-saving idea, but it may not be suitable if the benefits of your product are more likely to appeal to the Chief Marketing or Technology Officer. 

Before you reach out to anyone, take the time to determine your ICP. In some companies with less than 100 employees, you may choose to reach out directly to the CEO, as they’re likely to be responsible for making most purchasing decisions. 

However, in larger businesses, it often makes more sense to reach out to the c-level executive directly responsible for the product you’re selling. They can often be your key to entering into a more lucrative conversation with the rest of the business. 

  1. Understand C-Suite Decision Making Styles

Part of learning how to sell to the c-suite is understanding how executives make purchasing decisions. C-level executives are often driven by the same goals, such as improved revenue or team productivity, but the way they make decisions can vary drastically. 

For instance, Charismatic decision makers are constantly looking for their “next big win”, and want insights into how a solution will help them achieve their goals. “Thinkers” in the C-suite are more cautious and precise, who tend to be methodical about choices, and require access to a lot of data. Other common decision making styles include:

  • Skeptics: People who are inherently suspicious of anything new. They’re risk-averse, and require reassurance and validation of a solution from a respected thought leader.
  • Followers: Disciplined leaders who follow the guidelines set by other members of their team. They implement tried-and-true approaches based on their past experiences.
  • Controllers: Self-reliant perfectionists and micro-managers who are driven by a fear of failure. They need to feel ownership over the idea you present. 
  1. Navigating GateKeepers

One of the reasons selling to the C-Suite is such a complex process, is it can be extremely difficult to bypass the gatekeepers that protect their interests and time. There are a few different ways you can find ways to “overcome” gatekeepers. 

For instance, depending on how difficult it is to reach your c-level executive, you can also consider connecting with other people in your target company, to see whether they can help champion your solution to the board, such as VPs and department managers.

Using your employees’ existing connections can also be helpful. Someone in your company may already have a connection with someone in your target company. They may be able to make an introduction that helps you earn the trust of gatekeepers, and eventually c-level executives. 

It also helps to show some respect to the gatekeepers when selling to the C-suite. In other words, CC the executives assistant in the email, or reach out to them before you ask for a meeting directly.

Selling to the C-Suite: Best Practices for Pitching

One of the biggest differences between selling to C-Suite executives, and selling to other employees and consumers, is how you pitch your product. C-level executives generally don’t care about the “features” your product or service can offer. They’re looking for outcomes. 

You need to rework your pitch to present yourself as a “crucial solution” to an existing problem. This means conducting extensive research to find out what problems your executive is facing, what issues they care about, and what opportunities they could be missing out on. 

The more time you take to personalize your pitch to the needs and pain points of the executive, the more likely you are to be successful. Here are some common strategies for “pitching” to an executive. 

  1. Show How Your Solution Serves the Executive’s Goals

One way to make your sales pitch more appealing to a C-level executive, is to prove to them that you can help them achieve their specific goals. To do this, you’ll need to understand exactly what the C-level executive is trying to accomplish (such as increased revenue or improved margins). 

Take the time to gather as much information as you can about the executive and their targets. Build rapport with gatekeepers, and ask open-ended questions to collect insights. Leverage champions in your target company for behind-the-scenes data. You can even consider reading articles and social media posts shared by an executive to learn more about them. 

Once you have the right data, use your own sales content to validate the benefits of your solution. Use case studies, statistics, and success stories to highlight what your solution is capable of. 

  1. Use the Loss Aversion Track

Sometimes, c-level executives aren’t driven to make a purchase by the goals they might be able to achieve. Instead, they’re more motivated by the desire to avoid potential losses. Instead of explaining how your product or solution will deliver certain gains to your executives, consider talking about the problems they can potentially avoid. 

Many C-level executives are under a lot of pressure to avoid failures. Constant competition, demanding customers, and changing legislation can lead to a lot of stress. They all want to avoid negative outcomes that can put their reputations or roles at risk. 

With this in mind, instead of saying, “our solution can help you save money”, consider approaching the conversation with “Our solution can help you avoid losing profits and revenue.” 

  1. Treat C-Suite Selling like an ABM

Another way to approach C-Suite selling is with an account-based marketing approach. Ultimately, to capture and retain the attention of a C-level executive, you’re going to need to invest time and effort. You need to research their goals and pain points, and get to know their business. 

Becoming hyper-focused in your quest to find out what makes your contacts tick, and how you can support them in achieving their strategic goals isn’t too different to account-based marketing. 

This approach works particularly well in enterprise selling if you need the buy-in of various decision makers. Commit to building relationships and strengthening connections in this way, and you could improve the lifetime value of each deal too. 

Quick Tips for C-Level Selling

We’ve covered the basics of connecting with executives, and the best practices to use when pitching products and solutions, but there are still some additional strategies you can use to improve your chances of success. Here are some more quick tips for C-level selling:

  • Be prepared for negative responses: C-level executives are experts at raising sales objections. They have to be cautious about what they say “yes” to. If you got a lot of “no’s”, be willing to persevere, and change tactics when necessary. 
  • Get insights from your team: Your team members may be able to provide useful insights to help you connect with specific decision-makers. Engineers can be excellent resources when selling to a CTO, while financial experts are fantastic at understanding CFOs. 
  • Be willing to re-introduce yourself: Remember, C-Suite executives might forget about you from time to time. They have a lot on their plate, so be willing to re-introduce yourself, the benefits you can offer, and the purpose of your outreach.
  • Listen to the executive: Always actively listen to what your executive is saying. This will give you an opportunity to better understand their needs, goals, and pain points, so you can tailor your pitch accordingly. 
  • Communicate in their language: Ditch cheap sales talk. The C-suite is smart enough to see through sales gimmicks. Make sure you’re speaking their language, and presenting your solution in a genuine and authentic tone.
  • Connect with the executive’s team: Don’t ignore the gatekeepers and other crucial employees on your executive’s team completely. You might be able to find champions in this landscape who can advocate for your product or solution.

Mastering C-Level Selling

Selling to C-level executives can be challenging. Not only is it hard to reach the right executive to begin with, but you can struggle to pitch your solution in a way that achieves instant buy-in. However, following the tactics and strategies above will give you a good starting point to work with.

If you’re struggling with C-level selling, the easiest way to get an edge is to invest in expanding your skills. Existing experts have some fantastic insights into how to master executive level selling. View Gerry Hill’s AMA on this topic or book Gerry for a call through HSE!

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