The CEO’s Role in Complex Sales

Sep 19, 2022 | Sales Leadership, Sales Strategy

“As the CEO of an innovative company with a complex sale that sells to companies 10x to 1000x your size, growing sales revenue is critical to earning the valuation you deserve. But you’re making your already complex sale more difficult than it should be because you and your team are using outdated methods. Instead, elevate your sales by putting the proper strategy and tactics in place.” Alice Heiman

CEOs have an important role in driving sales and participating in large complex deals. I’m diving into this topic today. 

What I share is based on three facts that you’ll need to embrace to own your role in sales:

  1. As the leader of your company, you will always have a role in sales.
  2. Your role will change as your company grows and matures.
  3. Success in sales requires strategy (and you must be involved in developing that strategy.)

These are common themes you’ll hear on my podcast, Sales Talk for CEOs, where many CEOs I interview discuss their evolving but ever-necessary role in sales as they grow their company. So, what exactly is the CEO’s role in sales?

As CEO, you have a broader role in sales strategy and orchestrating a customer-focused team. In this article, I’m going to focus specifically on your role in large complex deals. 

3 Keys to Success with the Complex Sales

The CEO's Role in Complex Sales positioning

There are three keys to closing more complex deals, and the CEO plays a role in each. They are:

  • Strategy: Participate in the strategies with your team to advance the sale.
  • Positioning: Advise your team on how to position you properly with the right senior executives.
  • Coaching: Be sure your managers are trained, equipped, and held accountable to coach.
  • BONUS: Leverage: Use your personal brand and relationships to share insights and make introductions to advance the sale.

Let’s discuss each of these.


When your team is working on large, strategic, complex deals, you need to get involved. Knowing that your time is at a premium, I recommend advising your sales leaders on when to bring you into a strategy session and the prep you will need to participate. Once the strategy is built, together you can decide if you should participate in the execution by getting positioned with the higher level buying influences to make an impact. 

As CEO, in today’s buying environment you have to be involved in sales and understand the customer journey. Your role is  orchestrator. The CEO leads sales by coordinating sales, marketing, customer success, and operations and encouraging them to collaborate so that the focus is on providing exceptional customer experiences. In my blog post, How Great CEOs Lead Sales, you can read more about the CEO as an orchestrator. 


The CEO's Role in Complex Sales positioning sales team image

In the complex sale it is generally difficult for sales executives to get to the economic buyer and the senior leaders involved in making the decision. This is where sales and company leadership comes in. 

As we discussed in my podcast Closing Bigger Deals with expert Lisa Magnuson, CEOs should be brought in to strategically add value at various times during the complex sale. The episode includes Lisa’s advice on how the CEO can be used strategically to close big deals. 

But positioning in general can be tough. Sales reps often meet with one or two of the people involved in the buying process and don’t get positioned with all of the buying influences. That’s where good coaching is essential. It’s not the CEOs job to close the deal but there are important ways the CEO can assist.  

Deal Coaching

Deal Coaching is the key to landing and closing deals. Training is the first step to making sure everyone is using the same language and process, but your sales leaders must coach their teams on strategy and positioning, without continued coaching, they won’t get the needed results.  More specifics on this in my article The Sales Leaders Role in Conquering the Complex Sale.

While daily coaching responsibilities fall on your sales leader, I encourage CEOs to stay active and involved in doing some coaching and observing coaching. Make sure your leadership team stays sharp and on top of their coaching skills. 

The CEO's Role in Complex Sales coaching

But it’s not just the skill, it’s the time. Be sure you and your CRO/CSO or VP are holding them accountable to spend time coaching. The biggest complaint I hear from sales leaders is that they don’t have time to coach. Here’s some help on solving that challenge

It’s your job as CEO to make sure they have the time. Remove the roadblocks. If you have a VP of sales, CRO/CSO, they need to ensure the leaders are proficient at coaching, schedule the time, and are held accountable. 

Then, once in a while you should listen to a few calls to see if that coaching is working. Check out my blog post, Are You Listening?, where I encourage CEOs to listen to the conversations that your salespeople are having and what you should listen for. In the end, if your salespeople aren’t receiving the deal coaching (and the other coaching they need to develop their skills and manage their pipeline) you won’t get results. You should also take a look at the emails your salespeople are sending out. You may be pleased, but likely you will be appalled. This is worthy of your attention. 

Bonus: Leverage 

One of the most powerful things a CEO has is leverage though it’s not used often enough (Why, because sales is the job of the sellers, right!). I’m going to stop and tell a short and true story. 

At a small SaaS company I worked with, I had trained everyone on how to do strategies for large deals. They were doing very well and progressing more deals to close faster. They had a particularly tough deal going with a multi-billion dollar company, and it had stalled. They had tried all of the tactics I recommended but got no response. They had identified about 8 buyers involved but only had conversations and relationships with about 5. I recommended we call a strategy meeting and invite the CEO to see if he had any insight.  As we revealed to him who the decision makers were and who we thought was the economic buyer he blurted out, “I know him. I went to school with him. I know him really well.” To that, we all asked in unison, “Can you call him.” He texted him while we were all still in the room, and guess what, the deal was moving forward again. 

I could tell this same story a dozen times and change the company name and the CEO, but they are all virtually the same story. We fail to leverage the relationships we have, let alone that of the CEO. 

On every very large, significant, complex opportunity in the pipeline, take a look at who is on the buying team and see if you know anyone. Encourage your sales teams to ask everyone in the company if they have any relationships that can be leveraged. If you find people you can influence, strategize with your team on the best way to do that. 

Another form of leverage is your advice and thought leadership. As CEO, you know what you know best. Especially if you are the founder. You care about the problem your customer is trying to solve, or you wouldn’t be leading the company. While it is not your job to sell for your team, they should bring you in at the appropriate time with the appropriate people to talk at a higher level and share what you know about solving their problem and how others like them have solved it. 

I’m sure if you think about it you can find other ways to leverage your leadership. 

Your Role in Closing Complex Sales

You have an important role in opening and closing the largest opportunities at your company. Throughout the buyer’s journey, there are places where it is appropriate for you to get involved and where you can make a difference.  It’s important to discuss this with your senior team and make sure everyone knows how and when to get you involved. 

Alice Heiman

Alice Heiman

Alice is nationally known for her expertise in elevating sales to increase valuation for companies with a B2B complex sale that have exceptional growth potential. She’s originally, from the widely known Miller Heiman Group. Spending her time strategizing with CEOs and their leadership teams to build the strategies that find new business and grow existing accounts is her passion.  Her clients love her spirit and the way she energizes their sales organization.


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