C-Level Secrets – Tips for Connecting With The Top Brass

It may be intimidating to pitch and sell to top brass clients and C-level executives, but it always pays to reach higher… if you know how. Read on for some tips to help engage better with high-ranking officers.

RELATED: Four Tips On Selling To C-Level Executives

In this article:

  1. Engaging with C-Level Executives
    1. Start at the Top
    2. Forget the Features
    3. Understand their Priorities
    4. Level with Them
    5. Get Social
    6. Don’t Burn Bridges
    7. Be Pleasantly Persistent
  2. The Challenges of Selling to C-Level Executives
    1. Senior Executives Are Constantly Being Offered Something
    2. Most C-Level Decision Makers Prefer Referrals
    3. Their Time Is Limited
  3. C-Level Secrets: Copy the Things C-Level Executives do Daily
    1. Prioritize
    2. Get to the Point
    3. Able to Ask Great Questions
    4. Considers the Impact on the Organization
    5. Trust Others

How to Connect and Engage Better with the Top Brass and C-Level Executives

Engaging with C-Level Executives

“Shoot for the moon. Even if you miss, you’ll land among the stars.” This familiar adage comes from Norman Vincent Peale and has been used to inspire and motivate people around the world.

Why, then, do salespeople seem to shoot for the clouds and land among the trees? Why are so many calls made and emails sent that don’t even attempt to connect with the absolute highest decision-maker?

Cold calling the CEO is difficult, but not impossible — if you know how to structure your pitch and how to get past gatekeepers.

At Abstrakt, we’ve scheduled more than 100,000 B2B sales meetings in the last eight years, so we have unique insight and hundreds of thousands of hours put into mastering this skill. I’ve seen it in almost every new rep: fear of the owner, fear of the gatekeeper, fear of the 2nd gatekeeper (the dreaded executive assistant), and reluctance to even approach the challenge.

Some reps give in to this fear and go for the second best thing—mid-level managers.

Is it easier to get a mid-level manager on the phone? Absolutely.

Is it more productive? Definitely not.

A 2012 Harvard Business Review article reported a survey finding that more than 90% of C-level executives said they ‘never’ respond to cold calls or e-mail blasts.

What is a C-Level Executive? This is a high-ranking official in a company who usually makes decisions that affect the entire business. They are called such because they typically have a “C” in their job titles, such as:

  • CEO (Chief Executive Officer)
  • COO (Chief Operations Officer)
  • CTO (Chief Technology Officer)
  • CFO (Chief Financial Officer)
  • CMO (Chief Marketing Officer)
  • CIO (Chief Information Officer)
  • CSO (Chief Strategy Officer)

During an earnings call on February 24th, 2016, Salesforce CEO Marc Benioff credited their success to their ability to target the CEO.

“When I look at the largest transactions… every transaction was done with the CEO,” Benioff said. “I think it’s really unusual, and that’s why we’re really selling more enterprise software than Oracle or SAP.”

According to Anthony Parinello in the book Selling to Vito, targeting the CEO/President/Owner will result in:

  • A shorter sales cycle
  • Larger deal sizes
  • More add-on business

But, I assume you wouldn’t be here if you didn’t already know you should be reaching higher.

So, with more decision-makers guarding their time and companies adding more layers of protection to keep them insulated from pesky salespeople, how do we get a conversation? How do we keep a conversation going with the top decision-maker?

Here are some tips on how to engage with high-ranking officers of a company:

Start at the Top of C-Level Management

CEOs will occasionally push you down, but mid-level managers will rarely connect you up. If you don’t start at the top, it’s a steep climb to get there that risks relationships you build along the way.

Getting to know a company’s employees, their ranks, and levels can prepare you when you start penetrating the business.

As a sales rep, you should know that you should try and get to your C-level decision-makers as soon as possible. That way, you don’t have to exert too much effort making your sales talk on someone who isn’t even part of the decision-making process.

Plus, it’s better to get a rejection straight from the C-level executives. If you get one from lower-level managers, you’ll always be stuck wondering if you could’ve gotten a yes from the higher-ups instead.

Forget the Features

Features are great for an operations person, but the higher you climb, the more your conversation should be tied to the benefits to their organization.

People in C-level positions constantly think of ways to improve their company as a whole. If you can address the company’s challenges and offer benefits, then these executives will be more accessible and might be more ideal to talk to.

C-suite executives look at their company issues from a more macro perspective, so you should focus on the macro solutions you can provide. When you list down your features one-by-one, it’s not as appealing to someone higher up the corporate ladder.

They’re always going to be much more discerning. Also, these business leaders are going to be thinking: “What’s in it for me?”

Thus, you should answer that question before they even ask it.

Understand the Priorities of C-Level Executives

A CEO’s performance is tied to driving revenue, improving margins, and increasing the bottom line. They will spend their time in conversations that will help them achieve these objectives.

Remember that you should modify your sales pitch to accommodate for the person you are talking to. Therefore, for people within the C-level management, you shouldn’t be asking basic questions about their company.

In fact, you should already know enough to get straight to the point. If you ask questions about their company goals and background, they’re likely not going to think much of you.

You should be armed and ready and able to show your understanding of their company goals and needs even before they have to say what it is to you.

RELATED: How To Close Sales: 6 Annoying Sales Tactics To Avoid

Level with Them

Yes, this can mean being straightforward. More importantly, in this context, however, it means to make sure that the senior executives perceive you as an equal.

People naturally like to have conversations with people they perceive as having similar characteristics, challenges, and experiences to them.

If you want to appear to be on equal footing with them, then you should strive to be someone that they think wants the best out of their company. Instead of focusing on closing a deal, concentrate on the goals of the organization.

For a lot of business leaders, they tend to be bombarded by messages wanting to get a sale out of them.

To stand out, you should do some serious strategic planning on your positioning ideals.

Do you want to be a guide, a partner, or an advisor for the executive team?

Planning ahead is a smart and strategic way of establishing a better footing in your relationship with these business executives.

Get Social

business man hand working on laptop computer on wooden desk with social media network diagram | Get Social

According to a white paper published by IDC, “75% of B2B buyers and 84% of C-level/vice president (VP) executives surveyed use social media to make purchasing decisions.”

If 90% of C-level executives are ignoring your cold efforts, warm them up by sharing relevant information and engaging their content and industry on LinkedIn and other social platforms.

A blog post from LinkedIn selling provides the following statistics:

  • 92% of buyers engage if the professional is a known industry thought leader.
  • 88% of buyers accept connections through someone in their existing professional network.
  • 86% of buyers will listen if sales professionals provide insights about their business.
  • 46% of buyers will engage in the professionals has a complete LinkedIn profile.

In your C-level executive search, social media is a big help. Not only will it help you develop your target executives list, but you already find a way to connect and communicate with them in some way.

Don’t Burn Bridges With C-Level Connections

Speaking of getting social, try not to burn any bridges between you and anyone in leadership positions. You never know who is connected to who.

The funny thing about CEOs is, they tend to hang around other CEOs. This means that when you get a little overzealous in one of your conversations, you run the risk of hurting your reputation with multiple potential partners.

People in authority keep in contact with other people with the same status. Be confident in your message and confident in the value you bring.

However, you should also be respectful of their timelines and their priorities.

Be Pleasantly Persistent

Depending on the product you sell, you may already know that sales can mostly be a timing game. If the time isn’t right now, gain agreement to follow-up down the road at a time that makes sense and never miss a follow-up.

These C-level executives don’t want you calling and bugging their team. They don’t want you talking to their executive assistant every day while they’re in meetings any more than you want to do it.

It will save both parties time to agree to a follow-up and stick to it.

Add value in every interaction! Commit to never touch a base again (unless you’re in a softball league).

The Challenges of Selling to C-Level Executives

Senior Executives Are Constantly Being Offered Something

C-level executives are continuously bombarded with messages. Most of these are cold messages, all with offers and sometimes vague promises.

Being a part of any leadership team means that these senior execs have a say in the decision-making process, which is why sales representatives always try to target them. Your challenge is how to stand out among this sea of offers and promises.

Most C-Level Decision Makers Prefer Referrals

Since they’re receiving offers upon offers, they need a simple way of filtering these offers. One way to do that is by prioritizing referrals over cold calls or emails.

Just remember higher-ups like working with companies that already have a stamp of approval from their peers. Thus, be at your best when talking to any C-level executive because their word holds a lot of weight with other business leaders in their circle.

Their Time Is Limited

Given the fact that people within C-level management have a lot on their plates, their time is precious to them. Therefore, it requires quite a bit of incentive on a sales rep’s parts to be able to get a small chunk of their extra time.

Although it’s obviously much more challenging to do prospecting to CEOs, as long as you have the skills and you follow the tips listed above, it should come easier.

It’s not easy to catch the attention of top brass executives, but closing a deal with one is not impossible. You just need persistence and a little bit of planning as you pursue C-level executives.

Plan ahead and prepare for whatever issues the chief operating officer may raise when addressing your product or service.

C-Level Secrets: Copy the Things C-Level Executives do Daily

Another way to connect with senior executives is to understand what they do and how they do it. Using simple tricks, you can learn these C-level secrets, adopt behaviors to make your selling life much easier, and which are applicable even if you’re not in a C-level role.


Document Management Data System Business Internet Technology Concept | Prioritize

Any successful C-level executive has to nail the skill of prioritizing. Having the responsibility of managing billion-dollar accounts and sometimes hundreds of associates C-level executives have many demands thrust upon them. Their time and attention are divided but they still manage their tasks and monitor those of their managers and teams.

Get to the Point

Quite possibly because of time restrictions, C-level execs know how to communicate efficiently. Therefore, they know how to get to the point and will respect anyone who is not wasting their precious time.

Able to Ask Great Questions

C-level executives ask powerful and thoughtful questions despite not always knowing, or being involved with, the day to day work. Their techniques allow them to stay up to speed on subjects to yield helpful information.

Considers the Impact on the Organization

All decisions a C-level executive makes will be in the best interest of the business. They will always consider how decisions will impact performance and run a risk analysis to weigh up positive and negative outcomes. This C-level secret is something we can all adopt and improve our decision-making process.

Trust Others

C-level employees need strong teams which they can trust to get the job done. They promote this culture through empowering others, strong leadership, training, coaching, and succession planning.

These are all strategies we’ve used to great effectare there any that I missed? Have you experienced success using similar tactics? Share your thoughts in the comments section below. 

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Editor’s Note: This post was originally published on May 16, 2018, and has been updated for quality and relevancy.

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