Tighten Talent Acquisition Strategies to Compete in the Challenging Labor Market
Tighten Talent Acquisition Strategies to Compete in the Challenging Labor Market

Why Sales Transformations Fail and Critical Steps to Avoid Common Pitfalls

Heather Hall, Director Digital Strategy and Transformation

The big picture: In today’s virtual selling environment, revenue-aligned organizations must adopt a different mindset to drive successful sales transformations. Technology alone is not enough for successful digital transformation in sales; practical considerations and change reinforcement are crucial.

Important takeaway: Business leaders should prioritize technology stacks that improve buyer engagement and simplify seller workflows. Other important considerations outlined below include understanding the internal adoption culture and segmenting sales accordingly. Also, anticipating and engaging all likely users are among the critical steps to avoid common pitfalls.


The statistics are well known. When deploying sales-enablement technology or strategy, the first 45 days are the most critical. Twenty-one days is typically how long it takes for most sales changes to form a habit within an organization. And a message usually requires seven marketing touches to stick.

These are basic considerations for business leaders deploying transformational changes in a revenue-aligned organization. But in today’s virtual selling environment, successful transformations require much more, and it begins with the leaders adopting a different mindset and approach than many organizations have has traditionally been used in many organizations.

Gartner projects that 65% of business-to-business sales organizations will adopt data-driven decision-making, built on technology that unites workflow, data and analytics by 2026. To be effective, organizations must prioritize technology stacks that incorporate improved buyer engagement, data-driven seller actions and simplified seller workflows.

Imagine being able to accelerate from seven marketing touches to sales-accepted lead to sales-qualified lead that is primed and ready for closure.

Adoption Depends on Guided Change

When thinking about digital transformation, especially in sales, there is often an over-rotation to technology and technologically enabled processes. The practical considerations of how to deploy solutions for users, drive adoption and reinforce change are left to the last minute, slowing implementation and increasing resistance.

Suddenly, prospects who have engaged in the marketing programs are left in limbo, likely researching other options because the salesperson assigned to them cannot or will not engage in the tools put in place to ease their pursuits. This reminds us of the adage that you can lead a horse to water, but you cannot make it drink.

Before embarking on any technological sales transformation, consider these additional critical steps:

  • Understand the internal adoption culture. Just as prospects and customers are segmented to identify potential and upselling opportunities, sales should be segmented the same way. By understanding personas such as those who are confident in technology adoption but are resistant to change and need proof that something will work before they commit, organizations should anticipate and build enablement and ongoing training that engages all likely users.
  • Build an influencers tiger team to help identify friction or needs in deployment. Influencers can be excellent early adopters. They not only help identify potential challenges or supplemental needs as illustrated through their day-to-day jobs but can also help to build consensus better than those who do not sit inside the sales organization.
  • Consider different segments as solution is deployed. If the sales organization follows a traditional adoption curve, business leaders should consider a phased deployment approach that pairs more conservative or skeptical sales team members with a cohort of early adopters and influencers who can help build the case for change. Often, it’s less about the technology presented and more about the request to work differently that meets with resistance.
  • Treat the full launch not as a point in time but as an introductory 45-day cycle. It will take time for sales teams to build habits and routines. By treating the launch as an ongoing effort with microbursts of enablement, coaching and small wins, you can build momentum across the organization.
  • Promote the wins. At the beginning of development, use cases or ROI statements to support the reason for change. Revisit those and connect them to tangible proof to reinforce the impact of the sales transformation. By doing so, you establish value as it relates to wins.

Following a simple, structured approach to deploying technology in a diverse sales organization that considers unique seller dynamics, companies will see faster, higher returns in their investments. When the original intent of a sales transformation is to drive higher margin or average sales and claim greater market share, it’s time well spent.

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