The Importance of Sales Readiness in Digital Transformation

Originally published as part of, “The Day Before Digital Transformation” by Phil Perkins and Cheryl Smith

Most CEOs leading digital transformation efforts, whether highly successful or not, will tell you that when reflecting on their past endeavors, the one thing they would have made more of a priority, and done more of, is invest in the readiness of their sales organizations, including:

• Continuous sales learning.  Successful digital organizations continuously educate, train, and coach sales representatives to become consultants, not salespeople who drop off product or portfolio brochures.  Time spent internally in training and coaching versus time spent outside the organization prospecting clients can feel like it is taking sales reps off the critical path, but it is not.  It is focusing on long-term gains over short-term success.
• Continuous product learning. As the pace of change accelerates, it will start to outstrip your sales team’s ability to keep up, particularly as these representatives are increasingly distant, deskless, and digital. To overcome these frictions and challenges, effective solutions are emerging to drive ‘sales readiness,’[i] which enable the sales leadership to better mold the sales representative’s knowledge and behaviors to the new approaches. 
• Continuous feedback cycles.  There are a multitude of new technologies that help individuals get direction from their manager by recording their core presentations and sales discussions to check the pace they deliver the message, the amount of time they use filler words, etc.
• Collaborative marketing and sales partnership.  Establishing a specialized account-based Sales/Marketing team to reach high-value customers has proven to be effective in many digital transformation efforts.  Marketing and Sales collaborate to create personalized buying experiences for a mutually identified set of high-value accounts.

Maintaining your current customer base is critical at the outset of your transformation effort, and even more critical if you are financing your transformation efforts from current profits and cash reserves.  Unfortunately, many digital transformations stop before they start because executives are worried about how it will impact their sales force.  Any changes that make sales representatives uneasy can have them heading for the doors, taking critical customer relationships with them.  It is important to protect the existing customer base, of course.  Which means that the current sales representatives are critical to the new efforts. 

To help them better understand how to transition, consider bringing in sales leaders who have solid experience with digital sales.  These leaders must be empowered to develop and/or (eventually) replace the current sales force to make sure representatives are comfortable and experienced in newer digital selling techniques, such as social selling.[ii]  As we mentioned earlier in the chapter, digital sales often have more stakeholders to approve a decision, so sales representatives must also be able to master challenger[iii] and advisory[iv] selling methodologies over focusing just on traditional relationship and feature-based sales.

When starting the business development transformation based on a new digital solution, start with a guerilla team that can evangelize the solution and test out every aspect of acquiring a new customer.  These are a rare breed of business development individuals we call Market Finders.  They are excellent at listening to potential customers and adapting the solution to meet their needs.  A great sales executive excels at deal creativity, a great Market Finder excels at solution creativity. It is important that Market Finders can identify the early adopters who will take a risk on a new solution.  The guerilla team needs to identify the correct long-term customer stakeholders, help customers see things differently by educating them on how the technology can be applied to create benefits, develop messaging and collateral, optimize the pricing model, and operationalize the sales process for scaling. 

The Market Finders must also ensure that it is easy to work with your new organization. Traditional organizations will have legacy approaches to sales.  Often this process is led by the legal, or a combination of legal and procurement teams.  It is time to tear down some of the old barriers so that processes are straightforward and simple to bring in new customers while satisfying legal and regulatory requirements without adding new barriers. Once it is developed and proven to be successful with the carefully selected representative customer base, the guerrilla team can train the rest of the sales organization on the storytelling and processes.

After the solution is established with early adopters, the full sales organization must be prepared to grab as much market share as possible before competitors are able to copy and improve upon the solution.  It is important to position your organization as the market leader.  Consequently, your digitization strategy needs to have some unique feature or capability to it.  If you are simply copying another organization’s strategy, your sales team will spend most of its time trying to educate the prospect on why not to use the market leader.  With a market differentiator your sales representatives can focus on validating the buyers’ predisposition to buy versus trying to sell the customer on why to go your solution versus a competitor.  A prospective customer’s internal staff will be biased to a clear market leader because it is always the safe choice, e.g., buy IBM.  A market leader approach shifts the sales strategy to ‘why us’ away from ‘why not them.’

In the early stages of digital transformation, the organization must address a few critical issues:

• Does the sales team believe in the product and want to sell something new?
• Does the new solution require the sales representative to sell to stakeholders outside his or her experience and navigate a more complex organization?
• Do they have the skills to sell the more complex solution?

The top sales representatives are likely to be the most apprehensive about introducing new solutions to customers. They have invested a tremendous amount of time and energy building trusted advisor relationships with customers, and they will smartly maintain a high hurdle to introducing new factors into those customer relationships. The sales representatives that have struggled to make their quotas are often looking for a shiny new ball to sell, so they will often become very engaged, but their output tends to be low. 

Most organizations address these issues by increasing the aggressiveness of sales quotas.  This can help create short-term revenue, but when the maturity of the overall organization does not get the benefit of the momentum created, it is quickly followed by a pullback in revenue and profits in the following year.  Reaching for quick revenue does not create predictable/repeatable revenue.  It damages client relationships, creates pricing concessions that are difficult to rollback, requires investment in infrastructure for short-term revenue that ends up underutilized, and hurts talent loyalty causing turnover and lower delivery quality.  It is marked by telltale signs of a feeling of “burning hot” and an inability of the sale force to enjoy their newfound success. 

The war for top digital sales talent is just as fierce as the war for top engineering talent.  Almost every organization will see 80% of their sales come from 20% of their sales representatives.  Every organization on the market is after those sales leaders that are delivering the 80%.  

On the surface, digital sales cultures are vastly different than digital engineering cultures.  Digital sales require navigating uncertainty, persistence, and fostering a sense of healthy and positive competition.  But when reviewing the new engineering and technology team requirements, their preferred development methodologies also introduce the same components into the culture: the ability to navigate uncertainty, persistence, continuous education and mentorship, cross functional collaboration, and foster a healthy and positive sense of competition.  It will be up to the leaders to understand and accept these new culture components and learn to not only manage effectively inside them, but to lead the changes needed to instill them into the organization’s day-to-day culture.

[i] “What Is Sales Readiness — And Why Should You Care?” Jim Ninivaggi, Forbes Councils Member, Forbes Business Development Council, Council Post, February 20, 2018.

The concept of sales readiness has spawned an entire industry today.  We have selected a Forbes article here as a reference to begin to state the difference between sales reference and sales training, but there are dozens of excellent articles and blogs on the subject.  Search the term ‘sales readiness.’

[ii] “Social selling,” Wikipedia. https://en.wikipedia.org/wiki/Social_selling.

[iii] “The Challenger Sale: Compete and win in a customer-empowered world,” Gartner.   https://www.gartner.com/en/sales-service/insights/challenger-sale.

[iv] “What is consultative selling?” www.hubspot.com.