How to Succeed at Sales Transformation

Katherine Lovelace

Over the last fifteen years, I’ve directed dozens of large-scale sales transformation initiatives with companies of all sizes. Here’s one truth I’ve learned: While operational transformations can be tough for any business department, B2B sales organizations often struggle more than others—particularly when implementing new technology. 

Over the last fifteen years, I’ve directed dozens of large-scale sales transformation initiatives with companies of all sizes. Here’s one truth I’ve learned: While operational transformations can be tough for any business department, B2B sales organizations often struggle more than others—particularly when implementing new technology. 

Why is that? And what can you do to clear obstacles and ensure maximum ROI? 

In this post, I’ll review the reasons many sales organizations face unique challenges when undertaking a transformation initiative, and I’ll highlight the key elements necessary to help them achieve success. I’ll also outline some real-world do’s and don’ts from sales technology transformations I’ve witnessed firsthand over the course of my career. Finally, I’ll clarify exactly what you should expect from a vendor when it comes to executing a successful sales transformation initiative at your company.

Salespeople Thrive on Peer Knowledge and Efficiency

I wish I could say there’s an overarching reason salespeople react with greater difficulty to sales transformation initiatives–but it’s not that simple. Sales is both an art and a science, and salespeople are generally very driven to succeed, even in tough situations. I think the most important thing to bear in mind is that salespeople are best motivated when they understand why change is valuable.

Remember, there’s no major in college for sales. Most account execs have never had formal training on how to sell to executives, for example. Skills are typically acquired on the job, through hard-earned wins and losses, or by listening to people who have “carried a bag,” so to speak. Not surprisingly, then, sales reps tend to stick with legacy systems or methodologies passed down through the trenches because that’s what they know. That’s what has always worked. 

Nevertheless, Gartner estimates that today’s average virtual selling tech stack includes at least 13 different technologies. Salespeople are constantly being asked to add new solutions and try new approaches. The problem? Learning new things takes time. Time is money. And while benefits might ultimately become apparent, most reps will just default to what seems faster and easier unless they see up front why change will make them better at what they do.

Unfortunately, given today’s rising SG&A costs and uncertain economy, sales organizations don’t have the luxury of stagnating any longer. Informed buyers and competitive pressure make it nearly impossible to hit numbers using old approaches. Transformation efforts, particularly those that include new technology designed at elevating win rates and boosting productivity, are becoming more urgent. The key is figuring out how to deliver that “why” to sales organizations, so you can successfully execute these projects with minimal pushback and maximum progress.

Key Elements of a Successful Sales Transformation Initiative

Throughout my career, I’ve helped numerous sales organizations work to implement new technology solutions successfully. I’m not going to lie: It isn’t always easy. But with the right elements in place—namely, people (organization) and process (approach)—I’ve seen companies significantly streamline efforts, eliminate frustration, and accelerate time to results. 

People: Successful Transformations Start at the Top

As I mentioned earlier, salespeople learn best from their leaders and peers—people they trust to show why a project is both critical and feasible. That means large-scale sales transformation initiatives must demonstrate buy-in from everyone at the top, on day one, so there’s no reason to doubt the rationale or the potential rewards. 


  • Sales executives must support the initiative visibly, prioritizing it in training, in hiring, and throughout department culture.
  • Leadership should further efforts by leveraging hand-picked internal champions—people who have the respect of their peers, who can communicate the value of the project, and who can demonstrate how the use of new technology leads to more wins.

Process: How You Execute Transformation Determines Its Staying Power

As much as people play a critical role in sales transformation initiatives, processes also matter. Remember that change at this level and of this magnitude needs an efficient execution strategy for integrating the initiative into general operations, or sellers by nature will revert to their old habits. 


  •  To drive true transformational change, an implementation needs to be agile, focused on achieving and tracking specific outcomes and business value throughout the various phases of the project—and not simply a “one and done” training.
  • Advanced planning is vital in terms of operations, integration, communication, and understanding any functional barriers.

Do’s and Don’ts from Real-World Experience

Here are some good examples of how these people and process recommendations might look in action, based on real sales transformation initiatives I’ve seen over the years.

DO have executives show them the money.

At one company, execs recorded themselves introducing the sales organization to the new technology solution and the “why” behind their investment. Reps could literally see for themselves how excited and committed leadership was to helping them up their game

DO ask leadership to walk the walk.

Not only did one company give sales leaders first access to the new technology, ahead of the sellers, to ensure their buy-in and support, but they also integrated the tech into their sales QBRs to have peers share how they are using the solution to drive successful outcomes. Hearing excitement and success from inside the organization resonated far better with sellers than having external CSMs explain benefits.

DON’T give the wrong team control.

One company launched the solution through a centralized team of sales technology owners, not sellers themselves. Not only did this team not understand the “why” to help users resonate with the change, but they didn’t command the same level of respect that sellers have for their peers. When the tech team tried to reach out about training and usage, sellers simply ignored them.

DO leverage integration to reduce impact on sellers.

A Fortune 100 company leveraged an internal change management team to completely integrate the new platform into the existing sales tech stack prior to launch—giving sellers a “single pane of glass” to look through when utilizing solutions. This significantly reduced the technology noise and streamlined adoption.

DON’T let leadership drop the ball.

Sales leaders from one company failed to integrate the new technology into any processes or initiatives that would support adoption right from the start. Because leaders didn’t make the technology part of a seller’s daily strategy, sellers didn’t see a need to fully leverage the platform. Consequently, they struggled to see ROI and gain market share as quickly as other companies.

DON’T offer training without the “why.”

In one organization, a sales programs team owned the messaging and training for the new platform. They only required sellers to take a 15-minute training video at the beginning of the year, and it failed to connect a “why” to the operational changes. Even six months into the implementation, sellers remained unsure of how or when to use the new platform—which of course slowed ROI progress considerably. 

Sales Leaders Need to Understand the Vendor’s Role

After reading some of these cautionary examples, you might be wondering why vendors implementing sales transformation initiatives can’t just “step in” and “fix” things. 

Short answer? It wouldn’t work. Especially not with a large global sales organization. Vendors can help provide a blueprint for success, and offer plentiful resources to bring that blueprint to life, but the execution needs to be owned and ultimately strategized by sales leadership and supporting program leadership (such as Revenue Ops and Sales Enablement) in order for the transformation to truly occur.

That’s in part because every change management project needs leadership support to succeed, but it’s also due to the fact that salespeople have that different set of needs. For sellers to move away from what they know and comprehensively adopt change, they have to have a relatable, value-driven “why.” And the way to achieve that “why” needs to be explained (and proven) to them by their peers. 

Sales transformations are clearly complex scenarios. I know many buyers wish there were a magic solution that they could simply turn on—poof!—to see instantly successful results. Vendors wish that, too. But the reality is that the best way to drive transformational results in a sales technology initiative is to put in the work at both leadership and operational levels, communicating with sales teams in the manner that’s most effective to sellers. Now more than ever, as competitive pressure looms large, sellers must clearly identify with the reasons for change to seize the tremendous value potential at stake.

About the Author
  • Katherine Lovelace

    Katherine is a business strategist with over 13 years of experience in operational strategy, business process re-engineering, business case analysis and change enablement. She holds an MBA from the Wharton School.

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