What CEOs Don’t Know About Sales Transformations (And How It Can Hurt Them)

Brian Williams, PhD

One of the best parts of being a consultant is getting to know CEOs. Compared to the past, most of today’s senior executives really “get” sales. They understand the importance of consistent, sustainable top-line growth. And they have welcomed Chief Sales Officers with a seat at the “big boy” table.

Despite that, there’s a lot of things CEOs don’t understand about sales, especially when it comes to sales transformations. And for many, what they don’t know, can really hurt them. CEO knowledge gaps are a less obvious, but deadly contributor to sales transformation failures.

Re-engineering the sales function is a massive undertaking. Done correctly, transformations guide companies safely through turbulent markets. Botched transformation efforts become massive distractions, triggering a downward spiral in sales performance.

When it comes to sales transformations, a CEO’s impact is tied to their level of understanding around five critical factors:

  • It’s a journey – Sales transformations don’t happen overnight. There are many moving parts to sequence and multiple stakeholders to align. CEOs should expect (and demand) ongoing pivots and refinements, but timelines can’t be rushed.

  • Linked to the strategic agenda – Sales transformations must connect to the broader corporate strategy. It’s the CEO’s responsibility to ensure that this linkage is clearly communicated. Setting this tone and requiring support from all functions (IT, HR, Ops, Marketing, etc.) is essential.

  • Active CEO engagement – Sales transformations are complex and dynamic, so CEOs must keep these initiatives on their immediate radar. They should demand meaningful updates during each executive team meeting. And they must continuously clear roadblock and redirect resources.

  • Internal politics are brutal – Sales transformations will also trigger negative reactions from some. Change is threatening and there’s a natural bias to pay too much attention to the loudest, but not necessarily most informed voices. CEOs must be keenly aware of signal versus noise and snuff out distractions or gamesmanship when they see it.

  • Smart management is the unsung hero – Sales transformations are often any company’s most complex and risky undertaking. The right program and change management will make or break the effort. CEOs need to marshal the right investments and organizational support.


The best CEOs use this knowledge to partner with their CSO to create a driving force behind their sales transformation. A savvy CEO will demand:

  • Early engagement in sales transformation planning. This includes a fact-based discussion of the rationale, scope, timeline, and expected ROI.

  • A well-constructed communication and change management plan. A quality plan explicitly links to the corporate strategy and maps all stakeholders, messaging, and actions.

  • Definitive milestones for holding the sales team accountable. This must define the leading, lagging and behavioral metrics for each phase in the transformation.


A CSO’s priority is to educate CEOs about these five issues. While not directly responsible for detailed execution, CEOs will make all the difference in the success of a sales transformation.

Are you a sales leader planning or managing a sales transformation? Or, are you a CEO or senior business leader in a company executing major change in the sales model? We’d love to share our insight, including learnings from good and bad transformations.

Contact us and let’s explore how you can harness the power of a sales transformation to achieve lasting sales improvement.

Brian Williams, PhD

Brian Williams, PhD

Researcher, consultant, and sales leader, Brian uses a data-driven approach to drive sales effectiveness. His clients include leading sales organizations in financial services, technology, healthcare, and professional services. Using insight from academics and change management, Brian helps senior leaders and sales enablement teams understand and succeed in today’s more demanding market. His research has been published in Harvard Business Review and other outlets.