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David Jacoby

By: David Jacoby on June 9th, 2021

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Selling to Key Executives: 5 Questions You Must Answer

Sales Process | Building Relationships | Call Planning

Are you struggling to gain access to and effectively sell to key executives?

If so, you're not alone. Many sales professionals find it challenging to navigate the complex world of B2B sales and gain access to decision-makers at the executive level. But don't worry—we're here to help. In this blog post, we'll share five essential questions you must answer to sell to key executives successfully.

But First: Shift Your Mindset for Success

Every sales leader wants their team to “sell higher,” and it’s easy to understand why.

Senior-level executives can make bigger decisions faster than the typical buyers salespeople engage with: low-level technical users, program managers, and mid-level executives. As Marc Benioff, founder of, once noted, “When I look at [our] largest transactions … every transaction was done with the CEO.” Benioff’s experience is typical of many sales organizations.

Suppose your solution's costs and potential impacts are significant, radically new, or different from the status quo.

In that case, a senior executive must ultimately be involved in the decision-making process. But according to an article in the Harvard Business Review, senior executives consider less than one-fifth of their meetings with salespeople valuable. One problem is the mindset: Salespeople are most comfortable discussing the features of their product—the type of conversation a technical user would be interested in—but not how their solution impacts the bigger picture.

Key executives, on the other hand, operate at the strategic level.

They have to look at issues from an organization-wide perspective, not just at the department or program level. So, to have productive conversations with senior executives, you must change your mindset from the tactical (i.e., your product’s features) to the strategic.

OK, Here Are the Five Essential Questions You Must Answer to Sell to Key Executives

  1. What business outcomes can you help the key executive achieve?
    In many cases, salespeople struggle to quantify the business impact of their solution or fail to understand how their solution will influence important KPIs.

  2. What makes you, your company, or your solution different?
    This question is particularly relevant if the buyer already has an incumbent vendor.

  3. How will your solutions impact the key executive’s organization and stakeholders?
    This is a challenging question for most salespeople because it forces them to focus on the bigger picture, just like a senior executive.

  4. Can the key executive (and others in the organization) easily and effectively work with you?
    The financial impact isn’t the whole story. Senior-level executives don’t want more problems on their plates, so they want partners who are easy to work with.

  5. What is the long-term value of working with your organization?
    Senior leaders are not just concerned about the short term; they want to partner with companies that offer long-term benefits such as technological or competitive advantages.

Answering these questions will require you to do substantial pre-call planning and research. You can’t “wing it” when meeting a senior-level executive. But the extra effort up front will pay off when you have more meaningful sales conversations with senior executives.

💬 Join the Conversation

What strategies have you found most effective for engaging senior executives in your sales role? Share your tips and experiences here.

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About David Jacoby

As a Managing Director at Sales Readiness Group, David helps large B2B sales organizations improve sales performance. Previously, David was a Principal at Linear Partners, a sales consulting firm providing sales strategy, sales operations, talent management, and interim management services to emerging growth companies. In the past, David has served as Vice President of Business Affairs of Xylo, Inc., where he was responsible for the Company's business development, sales operations, legal affairs, and financing activities.