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Selling to C-Level Executives: The No-Bullshit Guide

Chris Orlob
June 9, 2023

Selling to C-level executives is not like selling to other buyer profiles. 

Typical gimmicks and sales prospecting tricks are not going to work on executive buyers.

Sales professionals need to get out of “sales mode” and become a trusted advisor and subject matter expert — whether you are selling to the CFO, COO, CIO, CMO or CEO — it’s critical to understand their world and everything that matters within it. 

This guide will help you navigate the peculiarities of selling to executive-level decision makers and teach you the right sales strategies for success when dealing with any CXO. 

Reasons Why Senior Executives Hate Being Sold To

Most sales reps struggle greatly when it comes to connecting with executive-level buyers on a personal level. 

This is because most salespeople fail to acknowledge how senior-level profiles think and make buying decisions.

Let’s go through them. 

CXOs are ridiculously busy

C-level decision-makers have extremely short attention spans. They have too many conflicting initiatives and don’t want to spend time on discovery calls — answering questions that anyone else in their organization could answer.

CXOs are less likely to respond to cold outreach

Senior executives are bombarded with ungodly volumes of outbound solicitations. Given the sheer noise and clutter they constantly deal with, sales teams have limited opportunities to break through the noise

CXOs are less likely to respond to unknown brands

Senior-level buyers are unlikely to acknowledge pitches from brands they’ve never heard of. Without help from marketing, it’s going to be even harder to break through. 

CXOs have gatekeepers for the purpose of evading sales teams

Let’s be real — gatekeepers are there to screen and filter out sales solicitations. 

CXOs don’t want to deal with entry level sales reps

Whether we want to accept it or not — experienced senior executives don’t want to interact with junior level SDRs with limited sales training. This post from Gaetano DiNardi sums it up. 

What Distinguishes Senior Executives from Other Buyer Profiles?

  1. CXOs are primarily involved in high-impact purchases. 
  2. CXOs want to deal with trusted advisors and subject matter experts. 
  3. CXOs prefer intros and referrals from a trusted source. 
  4. CXOs (sometimes) don’t need buy-in from other stakeholders. 
  5. CXOs may care less about pricing, and more about impact. 

The Right Way to Sell to C-Level Executives

Sales organizations need to level up their approach if they are serious about breaking down walls with C-suite executives. 

The reality is that executive buyers don't care about product features and functionality — they think strategically and want to see how your solution supports their key objectives. 

Here are 10 things that matter when selling into C-level decision-makers.

1. Start with LinkedIn (and sometimes Twitter)

Your sales performance can improve greatly if you understand where executive decision-makers “hang out” online. 

For example — webinars, threads on LinkedIn posts, Twitter discussions and Slack groups may be great places to engage with digitally savvy executives online. 

Now granted, some executive profiles are less active on social media than others — for example, the Chief Financial Officer from a healthcare conglomerate may not be as active on LinkedIn as a Series A SaaS CMO. 

However, plenty of senior executives are highly active on LinkedIn and Twitter — as well as various online communities — where you can see the types of content they engage with online. 

Social media profiles are a goldmine of information you can leverage to extract clues for crafting a compelling outreach message. 

But remember — use common sense and don’t send creepy cold pitches. By getting into their private life, you’ll only annoy them.

Generally, it’s best practice to avoid pitching executives on Instagram or Facebook unless you have already established some degree of familiarity with them. 

Selling to CFOs? Get Instant Access to the CFO Cheatsheet. 

2. Get a referral from a trusted insider

Using relationships and connections to broker introductions is by far one of the most effective methods for breaking down walls and landing meetings with executive buyers. 

Most companies are working with advisors, consultants and partners who have a direct line to the c-suite. Rather than cold outbound, sales teams can work with liaisons to get introductions.

3. Craft a compelling pitch

Most executives live out of their email inbox. 

Despite being heavily cluttered, an effective sales process can still work with a good old fashioned cold email. 

So, how do you grab the attention of a busy executive? 

Utilize these resources:

4. Utilize an omnichannel outbound approach

Salespeople need to understand how their buyer likes to be sold to. 

For example, some executives will never check a LinkedIn DM, but they’ll answer a phone call. 

Others will never answer a cold call, but live out of their email inbox. 

The lesson is never to rely on one channel, and test multiple approaches based on what you learn about your target buyer. 

5. Know their business inside and out

Like we said in the beginning, executives want to work with trusted advisors and subject matter experts — therefore you need to develop industry acumen in order to have intelligent discussions with senior executives. 

The type of knowledge you need to possess highly depends on the industry and the type of product you sell. 

For example, if you are selling ETL solutions to a CISO, you better be prepared to have technical conversations about data integration. 

If you are selling sales engagement to a Chief Revenue Officer, you must have intimate knowledge of their sales process, marketing channels, and other related information. 

It’d be smart to secret shop the organization before selling into the C-Suite, so that you’re prepared to discuss the flaws in their sales operations. 

6. Have other stakeholders and champions on board

C-level executives don’t often push purchasing decisions down the organization, but if they are involved in the buying process, they want their internal teams to support them. 

Before you engage with a senior decision-maker, connect with multiple stakeholders in the organization. LinkedIn is one of the best places to map out the “buying committee”. 

When engaging with various stakeholders at the organization, you’ll get a better idea of what their buying process looks like and how you can craft a more compelling case to an executive decision-maker. 

7. Focus on solving real business problems and communicating impact

There is no sales training program in the world that can help you if you can not perform these three critical steps:

  1. You need to understand the current state by doing proper discovery. 
  2. You need a crystal clear understanding of the problem, and the quantifiable impact of what happens if the problem is not resolved. 
  3. You need to effectively communicate the delta that exists between the current state and the future state. 

For example, if you are selling SEO solutions to a CMO — they don’t care about the exceptional functionality of your software — they want to hear about the economic benefits associated with organic traffic growth

Always aim to present the expected ROI of the buying decision. Talk in terms of business metrics and be prepared to share quantifiable ROI from other customers. 

Ideally, in collaboration with your sales management team, you should be able to calculate an estimated profitability outcome for the prospect’s business. 

Keep your estimates as close to real numbers as possible

8. Prepare case studies and references

You should be able to prove your words with real-life case studies. 

Include a success story of the most relevant customer (and make sure you have permission to create and share it) in your presentation to illustrate how exactly your platform contributes to achieving long-term business outcomes. 

Use your case studies as social proof, but avoid spending too much time talking about other companies. 

9. Use “loss aversion” tactics

Executives are only going to make a commitment to change if you focus on what they stand to lose versus what they stand to gain. 

In other words, the fear of losing outweighs the joy of winning.

Avoiding losses is a more powerful driver for executives than pursuing incremental gains. 

Therefore, by demonstrating what they miss out on while not using your product, you’re more likely to get executive buy-in. 

10. Understand their decision-making style

Your C-level executive likely falls under one of the five decision-making styles — it’s helpful to decipher their operating style to tailor your messaging accordingly.

  • The Charismatic: Described as enthusiastic and persistent, charismatics are quick to absorb and act on new ideas. While being open to risks, they are responsible and determined individuals. Despite initial enthusiasm, these people understand the need to reason their emotional decisions with facts. 
  • The Deep Thinker: These are the most difficult decision-makers to persuade. To make a buying decision, they’ll require as much information as possible, including real-life case studies, market research data, cost-benefit analysis, etc.
  • The Skeptic: This type of decision-maker is highly suspicious about everything you present to them until you win their trust. You should be ready to answer a lot of questions and stay incredibly diplomatic. A referral from a trusted source will help you establish credibility with a skeptic.
  • The Follower: Afraid of wrong choices, followers aren’t open to risk. They’re more likely to agree with you if you can show them how others have implemented your solution successfully.  
  • The Controller: These people are logical and objective in their decisions. Unlike deep thinkers or skeptics, controllers aren’t too interested in case studies and social proof. In your conversation with a controller, you’d better let them lead and ask questions. If they don’t convince themselves, nobody can impact their decision. 

You’ll get an idea of your executive’s decision-making style after your first interaction with them. 

Observe the way they respond to your pitch, ask questions, and present their concerns — and you’ll be able to figure out the triggers that impulse their buying decisions and include them in your sales communication.

C-Suite Executives Are Strategic Thinkers

C-suite executives perceive your value proposition differently from other roles. From their perspective, it only matters how it helps them solve an organizational problem and what it means for them in the long run. 

When selling to the C-suite, you should tailor your messaging to shift focus from immediate benefits to the big picture. 

At the end of the day, no matter what your buyer’s position is — the key to a successful sales strategy is understanding what’s truly important to them and addressing it in your sales process.

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