Driving Better Sales Enablement with a Digital Adoption Mindset

Bradley Chalupski
By Bradley Chalupski
Updated May 8, 2023

Humanity’s relationship to the technologies we create will never be the same. Corporate digital adoption that could be expected to take years has happened in months. These disruptions create opportunities for forward-thinking companies to improve their sales enablement processes. But they also come with hidden pitfalls.

Consider that Gartner research found that the average salesperson at a mature company needs to navigate through 13 different applications to go from prospecting to closed/won. This essentially takes employees whose job is to build human relationships and turns them into library administrators.

Adding layer after layer of complexity and calling it progress isn’t visionary. It’s a roadmap for an organization controlled by technology instead of empowered by it. Sales leaders must craft digital transformation strategies that enable employees to close more deals.

They can do this in three ways.

Focus on internal experiences, not technology silos

Strategies for digital adoption usually follow a pattern. During early-stage growth, ‘productivity’ technology adoption is rapid. But at 300+ headcount, it becomes clear only 20% of what’s being paid for gets used, so there is a pivot to increasing efficiency in the handoff between the technologies. At maturity, the productivity/efficiency strategy has created painful silos and no unified process– the focus pivots again to creating internal user experiences that allow reps to sell the way they want to sell.

Unfortunately, that final realization only happens after throwing hundreds of thousands of dollars at ‘productivity’ technology. For companies without strong leadership, it might never occur.

Sales tech stacks should be a centralized hub–including for remote sales teams–and foster a culture of intelligent work. Create workflows that enable support reps–not force them to do tasks that take them away from their core competency of building relationships.

“At the end of the day, technology is driving humanity forward. That applies to every single time you ask yourself ‘why did I buy all these tools?” It is part of a bigger picture. Because even though technology is driving us forward, we are still humans at the end of the day.”

~ Maor Ezer, Senior VP of Marketing, WalkMe

Create personalized selling experiences

Sales quotas often compel reps to emphasize quote volume. Brand is often sacrificed when a focus is placed on the quantity of opportunities rather than the quality. In practice, that often means abandoning deeper relationships in favor of using technology to pump out cookie-cutter quotes as quickly as possible. 

This is a mistake. Sales technology should cultivate personal connections between buyer and seller. Every buyer brings a unique mindset and set of expectations. Technology should help reps recognize what makes the other person unique and individual, let them give a signal that they have recognized it, and allow them to respond to that in a way that communicates we are on the same page. Building personalized experiences in this way differentiates brands and wins deals.

Break down barriers

B2B sales are conducted in a formal setting between professionals. Environmental factors, combined with viewing technology from a purely ‘productivity’ mindset, erect strong barriers between buyers and sellers. Instead, technology should be used not just to crunch numbers or iterate processes, but to facilitate human connections.

Enablement comes in many forms. Initial introductions that establish professional validation and credibility are a start. Deepening relationships can be nurtured by data-driven understandings of buyer pain and pinpoint delivery of relevant messaging and information to address it. Real-time responsiveness via chat and video offer collaboration opportunities. 

Ultimately, sales enablement technology needs to make it easier for teams to align on common ground, encourage personal connections with prospects, and create a single source of truth to guide buyers and sellers in their journey together.

Bradley Chalupski
By Bradley Chalupski
Bradley is Content Marketing Manager at DealHub, where he plays an integral role in creating experiences that help companies close more deals and capture more revenue.