Software Sales: Empowering The Challenger Strategy
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Software Sales: Empowering The Challenger Strategy

The Challenger Sale: Taking Control of the Customer Conversation, a book by Matthew Dixon and Brent Adamson, was released in 2011 and made a substantial splash.

Why did it garner such attention? It was, well, challenging—to say the least. Its authors claimed that sales based on relationships were ineffective, with buyers fed up answering questions from sales reps who delivered no value. It ran counter to many long-held beliefs, prompting industry sales leaders to rethink their approach to complex sales situations.

Justin Mares, a HubSpot contributor, discussed the book in a blog post, as well as part of his eBook, “The Best Sales Books: Summarized.” He provides a great overview which I’ll borrow from in order to share key highlights. Afterward, I’ll show how software sales teams can effectively put the Challenger strategy to work, focusing on using technology can facilitate the prospect education process.

Loyalty And The Selling Experience

“The Challenger Sale” was based on data gathered from more than 6,000 salespeople, making it one of the largest sales studies ever conducted. A major finding of the research is that customer loyalty is largely driven by the sales experience—not brand, price, service or product—which is defined by how a rep interacts with the customer.

So, how do successful sales pros engage with customers? Based on their research, Dixon and Adamson came up with five typical profiles of B2B sales reps. Though not mutually exclusive, these provide a glimpse into a sales pro’s natural way of dealing with customers. Here are the 5 profiles, along with 3 defining characteristics of each:

1. The Hard Worker

  • Doesn’t give up easily
  • Self-motivated
  • Interested in feedback and personal development

2. The Lone Wolf

  • Follows his or her instincts
  • Self-assured
  • Delivers results but is difficult to manage

3. The Relationship Builder

  • The classic consultative sales rep
  • Builds advocates internally
  • Creates relationships with prospects

4. The Problem Solver

  • Detail-oriented
  • Responds to stakeholders reliably
  • Ensures all problems are solved

5. The Challenger

  • Has a different view of the world
  • Has a strong understanding of the customer’s business
  • Prone to pushing the customer

As you likely surmised, the Challenger typically achieves the most success. This conclusion was supported by data, including that 40% of high sales performers use the approach. Further, only 7% of top performers were Relationship Builders, arguably the most widely used approach in sales and training at the time, yet the least effective.

What Makes A Challenger Unique?

According to marketing and sales strategists at Four Quadrant:

“The Challenger approach communicates a compelling value hypothesis and empowers the customer with new industry knowledge and business insights. Although this approach requires considerable homework up front, when done right, it results in a much tighter funnel with high conversion rates.”

Customers want to learn during the sales experience and Challengers deliver. Perhaps most important for those in sales areas such as software, the more complex the sale, the more a Challenger rises to the top. In fact, Dixon and Adamson’s research showed more than 50% of star performers in complex sales were Challengers.

Those are the results, but what’s in the makeup of the Challenger? Here are 6 distinct traits the book’s authors said these individuals bring to the job:

  1. Offers customers a unique perspective
  2. Has strong two-way communication skills
  3. Knows the individual customer’s value drivers
  4. Identifies economic drivers of the customer’s business
  5. Is comfortable discussing money
  6. Can pressure the customer

The 3 Ts

A Challenger Sales Rep Excels At The Following:

  1. Teaching customers ways to be more competitive
  2. Tailoring their sales pitches to hit the buyer’s hot buttons
  3. Taking control of the discussion and challenging the customer

Let’s unpack each a bit, beginning with a look at teaching, specifically as it is tied to sales presentations.

This Forbes article offers insight into how “The Challenger Sale” should be adapted for presentations. It notes:

“Your goal is to educate the audience. Unlike other sales presentations they sit through, this time they will have a better perspective on their problems. You are helping them do their jobs better, and this makes you much more valuable than simply having a good relationship or offering the lowest price.”

The Challenger tailors content based on how the prospective customer views the world. To ensure it resonates, a pitch should be personalized to the decision-maker and their objectives. This means taking care to ensure messages are customized to the role and communication style of the prospect.

“Taking control” relates to a Challenger holding firm on value. They should not be deterred by hesitation from customers. Instead, they should be comfortable asserting themselves. It really becomes more of a coaching scenario, intended to take a prospect through each step of the decision-making process.

When combined, the 3 Ts enable a Challenger to create “constructive tension” that will then motivate a customer to take action.

Tooling For Complex Software Sales

As those in complex software sales know, the key to success is the demo; today’s customer needs to see and touch to believe.

And it’s not in the Challenger repertoire, either.

A sales team needs to deliver a tailored, interactive demo that educates and is accessible to all the prospect’s stakeholders. This usually entails more than six people in about four different functions areas, so delivery ease is vital, as is speed - sales pros need to be able to reach prospects with their latest features quickly.

Virtual IT labs now offer a unique ability to captivate with full-featured demos of software in the cloud, regardless of complexity. As opposed to basic show-and-tell web conferencing, these platforms enable hands-on teaching via dedicated, production-grade replicas of a product at work in real-world scenarios, customized for a prospects’ existing environments. With the right tool, a salesperson can spin up reliable demos in minutes, anytime, anywhere, regardless of how are involved in the decision-making process.

It’s important that demos are as frictionless as possible today, especially whereas the average tech buyer is already 57% through the purchasing process before even speaking to a sales rep. The right platform can deliver demos without involving a prospect’s IT department, which is often hesitant to provide access to their network. It’s also important to keep customer acquisition costs low, and such a solution eliminates product shipping and travel, while also automating time-consuming tasks.

With virtual IT labs, sales teams can better control the conversation and deliver demos that prompt those a-ha moments that lead to deals. Yet, some solutions offer an additional, and arguably, just as an important function - Proofs of Concept (POC) that are also powerful and easy to deliver.

With virtual IT labs, you can send prospects a link to an easily accessible test drive even as you’re closing a presentation. This not only provides a practice-by-doing experience, but it also gives prospects the chance to try your technology without you around, showing confidence.

Further, the right solution can offer POC analytics that offers visibility into usage. Sales can understand how a trial is going, ensure prospects experience full value, see what features grabbed their interest. And if the target is stalled, they can jump in and offer assistance.

This technology is right in keeping with The Challenger profile. And just as the book and concept changed sales, when you provide this or any other profile with tools that more effectively teach prospects, tailor presentations and take control, uncontested results are sure to follow.

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