Greatest Sales Challenges Plaguing CEOs

Leading a company can be a challenge, even in the best of times. But when you’re in the effects of a global pandemic that caused international supply chain disruptions, domestic shelter-in-place rules, and an economic downturn, it can be even more difficult. Here are five sales challenges CEOs are facing right now.

Planning for Growth

One of the biggest challenges also happens to be one of your core business decisions. That is deciding where growth will come from especially with how things are right now.

Your growth depends on the strategies and execution plans you implement to make it happen. To be successful in your strategy, you need to consider what will significantly impact business growth. Let’s take a look at a few possibilities.

New Markets

To maintain steady growth, you can go after markets in your same area – so long as it is not saturated. However, if you feel like your market is saturated, then you may want to look at entirely new markets.


Another growth strategy to combat market saturation or to grow margin in general is effective pricing.  Your aim is to hit the sweet spot — a price that reflects the value your customers receive and that they’re willing to pay, and that allows your company to hit its growth goals.


The further you go in defining differentiators the more your messaging will resonate with the right customers. Decide what you want to be known for and make sure that your salespeople are clearly articulating your story to your target audience.


The simple fact is if you add the right salespeople, they will make sales and bring in revenue. The most successful salespeople are able to identify the gap between the customer’s needs and the products/services that your company offers and create value by tailoring messages that align with stakeholder/decision-maker criteria and your differentiators.

Cash flow

Another big sales challenge for CEO’s is stable cash flow. CEOs want to make sure they always have the available resources to do what they want, like investing in their company, hiring new employees, growing, etc.

Determine what your strategy is to invest your cash reserves. Know how much cash you need to keep on hand and what triggers you to know when and how to invest. Calculate the return on your investment and what your current runway is to recoup these costs. Paying attention to your cash flow and tackling challenges head-on is a great way to make sure you always have the funds you need to stay in business.

A cash flow strategy must be considered to ensure sustainable growth. If you wait too long to do something, you’ll miss opportunities. 

Hiring Good Leadership

CEOs are concerned about hiring, employee engagement, accountability, and leadership. 

According to Forbes, “19% of Forbes Council members said leadership issues were their greatest challenges.” Most often, CEOs will see if the sales leader candidate knows their industry and has a good track record of being a “good” sales leader. That is typically reflected in their previous company’s sales numbers and growth. 

They also look to see if the sales leader has contacts, can ramp up quickly, and then they will hire based on whether they like that person/they interviewed well. This is a typical approach but not consistently the most effective.

Have you thought about the size of your sales team? The team’s receptiveness? Your company’s culture? What level of authority do you want your sales leader to have? What role do you need them to fill within the company? These are all critical things to know when you are looking to hire a sales leader. 

Buyer Habits

Many customers are rethinking their investment priorities, consolidating vendors, and freezing their spending. According to Research highlights, in 2019 - 2020, “53% of buyers have reprioritized their spending and 38% have a spending freeze in place.” As a result, you should revisit opportunities to assure proposals are aligned to solving priority issues.

Cold calling and buyers have changed over the years. Buyers now do a lot of research before talking to a salesperson. According to Mediafly, there were five characteristics that buyers were looking for:

  • Demonstrating unique insights
  • Helping the buyer come to a decision
  • Understanding and addressing different stakeholder needs
  • Helping the buyer build support across their organization
  • Making it easy for the buyer to make a purchase

Remote Employees

More and more people are working these days remotely. According to Apollo Technical, “Since 2020, people have been meeting by video calls 50% more since COVID-19. During COVID-19, close to 70% of full-time workers are working from home.”

The sales challenge is in making sure remote employees and leadership are finding ways to connect and engage.

Social interaction is a huge challenge. While Zoom is an excellent solution for connecting virtually, most sales and business development leaders are in this space because they are social and enjoy in-person networking and interaction.

Being physically distant from their teammates and customers is causing workers to question their impact. According to FrontPage, “69% feel detached from teammates, and 63% feel detached from customers or end-users.”

To counteract some of these feelings, make sure your employees are taking advantage of social media and interacting with one another through LinkedIn groups, WhatsApp team chats, Slack, etc. Make time for fun with online games like trivia or a virtual happy hour. Build a more inclusive culture.

The Results

CEOs are facing several sales challenges like not knowing where growth will come from, stable cash flow, hiring good leadership, changing buyer habits, and more remote employee than ever before. But now that you know these sales challenges, you can face them and continue to move forward.

Enhance your leadership skills and proactively build your legacy.

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