Sales Training Online: Why You Must Sell to the CEO

December 19, 2020 / Comments (0)


Salespeople who sell at the higher executive levels often outperform the rest and when it comes down to executive leadership selling, it doesn’t get higher than the CEO.

Just take a look at this article concerning the importance of selling to the CEO from the Harvard Business Review.

But, there is an inherent fear that resides in many salespeople that makes them extremely uncomfortable about selling to the CEO, although logically, they can accept the fact that deals are signed off at the top, budgets can be re-allocated, and doesn’t it make sense to start the sales process with the person and people that can make deals happen?

Sales trainers and online sales training programs are full of strategies and motivational reasoning when it comes down to teaching salespeople to move up the value chain and engage with CEO’s and the executive leadership team, but for me and having seen so many salespeople over the years, the training hasn’t worked.

Too many salespeople operate in their own comfort zones rather than the right zone for maximum effectiveness and reward.

I should know because I was one of them — I was far happier dealing with line managers and the odd operational head because I didn’t feel intimidated by them and I could produce some great results that would please any sales manager or sales director…but I always felt there was something missing from my sales career development and that I could do more.

A meeting with someone who mentored me early on in my sales career left me under no illusion that I was not maximizing my success and simply adding unnecessary layers of complication to the sales process.

If you are not selling to the top, you are wasting your time.

He had worked in IT and technology selling for most of his career and learned very quickly that if you want to get a decision that would help you build a real company to company relationship, you needed to get to the top.

People come and go, but company relationships will be maintained, provided there is a good and consistent value proposition.

I started my sales career knocking on people’s doors trying to sell home improvements and slowly worked my way up to selling into the boardrooms of some of the worlds leading technology companies.

From that first meeting with my first sales mentor, I realized that I needed to devise and refine a strategy to get to the top of the tree and talk to the people who could really understand the value that I and my company could provide them.

Being a CEO is one of the loneliest jobs in the world — you are fighting external and internal organizational forces…plus yourself and your insecurities. I have personal experience here, and even as a private company, with no shareholders to worry about, there was still a huge amount of pressure on me to deliver results and to handle the responsibility that comes with employing others.

Corporate CEOs live in a totally different world and one where they are spending most of their time dealing with analysts, who are eager to get an insight into the next quarter’s results, which can, in turn, seal a CEO’s fate of employment or not!

There is also the matter of running the day-to-day business and making sure the business engine is running optimally to ensure that the results can be delivered and that is where the rest of the executives come into play.

The C-Suite or executive leadership team is the most important and influential group of people in the company and they are headed by the CEO.

Now, there is one thing I would like to clear up from the outset — the CEO is the top of the tree, but that does not mean that they will wield their power and overrule people.

I saw a post on social media recently that talked about not worrying about selling to the Chief Financial Officer (CFO) and moving directly to the CEO because the CEO will “take care” of the CFO.

Nothing could be further from the truth in my opinion because it is not the job of the CEO to take care of anyone, in a business sense and they are more reliant on receiving the right advice from other C-Suite executives rather than directing them as to what to do.

This is an extremely important point to understand, so you may well think to yourself that it may be better to focus on the individual executives rather than the CEO and you would be right…to a degree.

Over the years I have always targeted the CEO initially, but that is for reasons that I will explain in this article let me give you another piece of advice…forget any form of salesmanship and most of the sales training that you have received.

It doesn’t work.

Focus on providing factual and data-driven information and learn how to influence people rather than sell to them.

There is a huge difference.

Take a look at this article to get a much deeper insight:

“Sales Training: The Ultimate Guide To Help You Become A Key Influencer.”

Do people really buy from people?



I believe people engage with people and buy the value from them or their companies.

There have been many times where I have bought services and products from companies where I haven’t particularly liked the person concerned, but I have seen the value of those products and/or services to me, my company, or both.

I have also bought from people I have really liked, but when it came down to service and/or product delivery they failed, and liking them didn’t help one bit when it came to making my feeling known!

So let’s clear up that myth right now and start to focus on engaging with people, influencing them with knowledge, and then delivering a service, product, or both that gives them tremendous value.

A CEO is not going to be overly concerned with how nice a person you are, but they will be absolutely concerned with the value that you provide to their organization…their very existence depends on delivering value to their customers, and to deliver value, they have to buy value.

And that is where you come in.

Why start with the CEO?



Because you are starting from the top of the tree when it comes down to the day-to-day executive running of the company.

But before you go ahead and make contact with any CEO, you must learn to think like one.

Your value proposition should include a vision — the ability to look to the future, predict and prepare for it, plus to have an acute awareness of the history of your particular industry and market, will make sure you fully understand the “now.”

But you have to take a big picture view and not delve too deep into the weeds.

A CEO will combine this vision with strong leadership skills and decision-making skills — taking advice from a highly skilled leadership team is one thing…acting on it is another.

It is vital to think like a CEO and also to understand some of the problems that keep them awake at night and here are a few:

  • Hyper-competition — we are living in the most competitive economic environment ever.
  • Geopolitical uncertainty — the world is becoming increasingly more volatile and uncertain.
  • Regulation and Taxation — corporate regulation, environmental and taxation issues are liable to change.
  • Technology, innovation, and security — Cyber attacks are on the rise, innovation is an ongoing process and challenge along with having the right technology.
  • People — there is a never-ending war for top talent.
  • Finance — having enough capital to run an organization is a constant challenge along with making the right investments.

It is vital that you get in tune with the thinking of a CEO and in the article I’ve linked to above, I talk more about the research components that you can work through to help you, so I won’t go into them here.

Once you have a real appreciation of the role of a CEO, you can start to plan your approach and how to engage.

Now here is another important point — you should start your sales or influencing journey with the CEO and you may or may not end up back to them, but your deal is likely to be done with another member of the executive leadership team, depending on what category your business and it’s value proposition falls into.

But you should start at the top!

How to engage with the CEO

Sales-Training-How-To-Engage-With-The CEO


The best way to engage with a CEO is to communicate with their executive assistant — I have used this strategy throughout my career and it works.

And let me tell you to please avoid any advice that some trainers and gurus hawk and that is to blast through the assistant or “gatekeeper” as they are termed, with the goal of getting straight through to the top person.

As a former CEO, I had faith and trust in my assistants to make sure that my time was optimized and managed. The assistant is there to make my life easier and that will mean trusting them to field unnecessary calls and demands for my time. They are also more than capable of deciding what is important and when to put people through and if you upset the assistant by being too pushy or sales-like, then it will get straight back to me and we will then be starting off on the wrong foot.

Rule #1 for CEO engagement — respect the executive assistant.

My approach was to simply contact the assistant and ask for their help — I would very briefly explain the value I could bring to the organization and why I wanted to talk to the “boss” and then follow it up with a proposal.

I would ask the assistant to review the proposal and to then tell me if they thought it was appropriate to meet or talk with the CEO and on most occasions, I was put directly in touch with another member of the leadership team, who would welcome the fact that I had come with a recommendation from above.

On one occasion and early on in this process, the assistant not only gave me the details of the relevant executive leaders for my business, but they helped me re-write my proposal into their own internal “business language.”

This was invaluable to me at the time.

If you do manage to get through to the CEO, you must ensure that you value the one commodity that they are constantly battling with…time!

Along with the sleepless nights and the problems associated with them, the art of managing time during the working day is a precise art and if you waste it, you will certainly not do yourself any favors.

Make sure you are clear and precise when it comes down to articulating what I term, your “compelling value proposition” and get to the point.

Again, I cover this in the article I’ve linked to above.

In my own career, I was dealing with very large corporations, so the chances of getting in front of the CEO were limited and most of the time I was very nicely referred down to other members of the leadership and management team, but they were all very high-ranking executives at the very least…but I always started with the assistant to the CEO and I did manage to meet a few CEO’s in the process.

Your chances may be greater depending on the industry you operate in and the size of the companies you are dealing with, so just get out there and take that first step and connect.

But…do your homework!

Keep the CEO relationship



One of the mistakes I have made during my career is to work hard to get a high-level relationship, only to let it fizzle out over time because I was too engrossed in progressing the deal with other members of the leadership team.

I had worked very hard to get to a board member of a company and eventually signed a deal with my company.

I had a few meetings with his team after making my usual approach to the assistant to the CEO and eventually, I was granted a thirty-minute “approval ” meeting before the deal signing, which lasted well over an hour.

One other point to note — don’t fall the mere “approval” words and remember you are always under scrutiny. I re-located to the US from the UK, shortly after this deal, and one day in a restaurant with another client, I looked across and saw the board member in question, walking over to his table.

I managed to get a brief chat with him before I left and found out that he was now also based in the US and had been tasked with being the CEO of a subsidiary company that had just been acquired.

I should have known.

It is vital to keep relationships and especially when you have worked so hard, in the beginning, to get them — in this case, I was completely out of the picture and although I did manage to get into the new organization he was now heading, I had largely missed the boat on a load of opportunities.

Never rely on the CEO or any executive leader to keep in touch with you — they are far too busy and time-starved.

Make sure you keep in touch.


You have to get over any fears you have when it comes down to contacting the ultimate head of any company you are looking to do business with or to increase the level of business you already have with them.

Getting known at the top of the tree in customer organizations gives you the best chances of building a company to company relationship and one that is not in the hands of a few individuals.

The job of the CEO is an extremely lonely one and one that comes with a great deal of big-picture challenges that sit on top of the normal day-to-day business activities that challenge us all.

The CEO has ultimate responsibility for the vision, operation, and success or failure of the company…period.

But they are still human beings and have the same emotions and feelings as you and me.

But please don’t think they will use their power directly and just because you are able to present them with a compelling value proposition — they rely on key advice from their leadership team who they have empowered to run the respective business functions.

Make sure you respect the importance of the executive assistant and to me, they are one of the most important members of the leadership team.

Using the executive assistant correctly and respectfully, you will be able to more easily navigate through the corporate structure of the organization, plus get a feel for the internal language of the business.

You may well be pushed down to other members of the leadership team, but this will be a much more productive experience since you have been referred from the top.

Finally, make sure you maintain any relationships that you develop — it is easy to get caught up in the deal-making process and forget the people that got you there, or simply shy away from them because you believe they have served their purpose.

So go out there and make the conscious decision to move up the value chain…you won’t be disappointed and if you need any further help or clarification on this, please get in touch with me!


Neil Franklin


Last modified: December 23, 2020

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