6 Actions Sales Leaders Can Take for Managing Complex Sales While Working Remote

Jun 17, 2021 | Complex Sale, Sales, Sales Leadership

We’ve talked in the past about the sales leader’s role in conquering the complex sale. In fact, I have a free webinar you can watch if you’re finding it harder to close large enterprise deals. But as the world adjusted to the pandemic and more sales teams began working remotely, managing complex sales became even more challenging. Today, I want to share six actions sales leaders can take to manage complex sales – even while working remotely.

Understanding the Complex Sale and the Sales Leader’s Role 

Before we jump into the actions, let’s make sure we understand what we are talking about when referring to a ‘complex sale.’ Simply put, complex sale refers to a type of sale that is relatively large and resource-intensive. With a complex sale, there are typically many people involved on both the buying and selling sides.

With more people come more personalities and more thought processes. In addition, there may also be more technical complexities and integrations that come into play. For example, you may have the buy-in of all of the players on a deal, but if the IT person comes back and says they can’t make the integration work, the deal could be dead.

managing complex sales - leaders role


As the CEO, Sales Manager, or another leader of the organization, your role in the complex sale process is three-fold:

  • To clearly understand the complex sale and what makes it challenging. 
  • To understand your role in moving the sale forward. 
  • To learn how your coaching can lead to closing more of these complex deals. 

Leaders of the organization will always have a role in the complex sale, and conquering the complex sale requires strategy. As your company grows or you experience external factors like a worldwide pandemic, that role will likely change. And how you adjust will determine the success of your sales team. 

6 Actions Sales Leaders Can Take for Managing Complex Sales 

To help you manage complex sales in your organization, even while working remotely, take these six actions for success. 

Action #1: Hire Right 

Success in sales starts by hiring the right salesperson for your team. But quite often, organizations don’t get the hiring process right. This is one area you shouldn’t go alone. You need an expert to help you source the right candidates for your organization. 

Action #2: Set Goals 

Setting goals is a vital part of finding success in the complex sales process.  

When setting goals, don’t make it about hitting a quote. That is a lagging indicator, and by the time you realize that they may not have hit the mark, it’s too late. Plus, with complex sales, the sales cycle is much longer, so measuring in terms of quota just doesn’t work. 

Instead, measure in forward movement. Set markers that measure actions within the sales cycle that move the deal towards closing.  

And if you have a salesperson who isn’t hitting their markers and isn’t able to move the deal forward, after repeated coaching, you need to let them go. I can’t tell you how many companies I’ve seen waste so much money giving unsuccessful salespeople chance after chance after chance. Then, by the time they’ve called me, they’re like, “Well, I’m trying to decide if I should fire this guy or not.”

Here’s the reality: If you think you should fire them, you’re probably right. 

BONUS TIP: One of my favorite sales books of all time, and one I highly recommend to all the CEOs I work with, is ‘You’re NOT the Person I Hired!’ coauthored by my friend Barry Deutsch. It is the CEO’s guide to hiring top talent. 

Action #3: Educate on the Buyers 

Organizations spend a lot of time educating their salespeople on the product they are selling. They send them to boot camps, which now many are doing remotely. They download all the information about their products and services and even run them through some practice sales sessions. 

But the one thing many companies forget is to teach salespeople is about the buyers. Who the buyer is. How to relate to the buyer. What a day in the life of their buyer is like. Spend time teaching your salespeople everything they need to know about the buyers they will sell to and your customers and what matters most to them. 

Action #4: Allow Sales People to Shadow Other Sales People 

I’m often asked, “What is the one thing that my company can hone in on and focus on for the next four weeks so we can see a 1% improvement.” My answer is quite simple:  

Give your salespeople more time to shadow other successful salespeople, to hear from existing customers who know and love you, and learn from them! 

6 actions managing complex sales - job shadowing

By doing this, you allow your new salespeople to discover so many important questions that they need to ask to understand: 

  • Who were the people involved when you made the decision?  
  • What were they thinking about?  
  • What do they care about in terms of their company and the success of their company? 
  • What other initiatives might they have?  
  • Which products make the most sense?  
  • How to know if they need our solution?  

Sure, it’s easier to allow shadowing when you are making sales calls in person, but you can still make it work when working remotely.  

Action #5: Watch and Listen 

This is critical in ensuring the success of the complex sale. Sales leaders, and even the CEOs of companies, need to be listening to their salespeople’s calls, zoom sessions, or demos. They also need to be monitoring their written communication with clients. 

You are setting these salespeople loose into the world to represent your organization and products. You need to make sure that they are representing you in the best way possible. Think of it this way: how many cringe-worthy emails and phone calls do you get each week from salespeople from various companies?

I recently sent a CEO an email I received from one of his salespeople. He was appalled. Your people may be just as guilty. So, watch and listen to make sure they are not! 

Action #6: Lead, Inspire and Encourage 

As a leader in your company, your main job is to lead, inspire and encourage everyone on the team to be as successful as humanly possible. Each morning take a look in the mirror and ask yourself: “What am I gonna do to make my team successful today?”  

6 actions managing complex sale - leadership reflection

And remember, in the end, it comes back to company leadership and ultimately the CEO  when the salespeople don’t hit their number. When sales are down, stop looking around and look at yourself in the mirror and ask yourself, “What have I done to either inhibit sales or enable sales?” 

Without a doubt, managing complex sales can be a difficult process. By taking the actions I’ve provided, you can set your sales organization up for success.

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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