When the COVID-19 forced much of the world to go remote, organizations put a lot of thought and work into enabling employees to work effectively from home. That work involved consideration of time management, digital skills, personal effectiveness and emotional intelligence — skills that enable workers to meet their goals, even when working remotely.

The secondary attention companies paid to the digital upskilling of their salespeople, on the other hand, is not surprising. Field sales teams have had a hard time bringing themselves up to speed with digitization. Customer relationship management (CRM) platforms, sales funnels, chatbots, video calls and social selling have enabled digital sales processes, which have often taken bits and pieces of work away from salespeople, becoming a competitor of the traditional sales rep.

But this misconception went up in flames with the pandemic. Digital technology has become a fundamental enabler for any sales approach, in any industry. Business-to-business (B2B) sales was the first to make the switch to remote, but business-to-business (B2C), life sciences and business-to-government (B2G) sales have followed. In Italy, we have started calling digital sales “smart selling,” linking it to “smart working,” the Italian phrase referring to the work-from-home revolution.

Many human resources (HR) functions and sales organizations have tried to shift field sales to smart selling by handing out tools: buying webcams and Zoom subscriptions and telling their sales staff to “go remote”. Salespeople, being the adaptable, goal-driven people they are, have done so, to a degree of effectiveness. But smart selling — i.e., the full use of digital tools to support field sales — is not a “lift and shift” of a traditional sales approach. It is a reorganization of sales approaches in order to empower salespeople.

There are three core areas of smart selling:

The Top of the Funnel: Personal Branding

Salespeople can leverage digital media such as social networks to make their potential customers more aware of their personal brand. This process is a way for sales professionals to “own” a piece of territory that is traditionally the marketing team’s, because it puts salespeople in the position to start building thought leadership and a brand of their own.

This personal brand puts more power in the hands of smart seller, as they are now a reason for customers to engage with the company or consider their. Excellent salespeople can use their charisma and influence to persuade customers to buy, and excellent smart sellers can influence customers into including them on their shopping list.

For learning and development (L&D) professionals, this evolution has important implications. It means that organizations that want to embrace digital sales need to put in place multi-stakeholder projects that empower salespeople’s online presence. Training salespeople on how to write blog posts, for example, is pointless if the organization is not committed to enabling their salespeople to “own” a personal brand. Excessive red tape from the legal, compliance, communication or marketing team is a sure way to smother the fire of smart selling.

However, the L&D and sales teams can and should include other stakeholders in the definition of the boundaries of salespeople’s personal branding. Starting off with a few “pilot” reps who are given higher degrees of trust and flexibility is often a good idea. These salespeople can start paving the way for smart selling.

After that, training is necessary to teach salespeople to leave their traditional comfort zone. Content management, cognitive empathy, social media marketing, and even video creation or graphic design basics can be powerful skills to teach to smart seller, because they will help them craft content that can grow their personal brand.

The Middle of the Funnel: Digital Networking

Networking has always been a significant part of sales, especially in certain industries. If not networking, per se, referrals and event marketing have been key to acquiring new business and avoiding the stress and drop rates of cold calling.

Digital networking follows the same general rules as traditional networking. Many salespeople still don’t consider social media an effective tool for networking, but it is. Smart sellers create strong bonds with customers and prospects online, creating deals and establishing great relationships with people that they have never met in person.

Here, L&D should provide specific training that teaches tips and tricks on how to network effectively. The keys to digital networking are easy to explain, even if they are difficult to master:


A good networker has a giving attitude, rather than a requesting or bartering attitude. Rather than doing favors on a quid pro quo basis, they always try to give value to their contacts in the form of information, insights — or favors.


Networking should not be hasty. Salespeople need to meet their quota, but being overly aggressive can push potential customers away. Smart Sellers nurture relationships that turn into business in their own time.

Digital Skills

Good networking mixes different channels and media. Smart sellers keep in touch with customer and prospects any way they can, whether through personal messages, courtesy video calls, personalized content, tags and comments, responses to stories, invitations to webinars, live interviews, and podcasts. The possibilities are numerous, and salespeople need training on how to handle this complex digital networking ritual.

The Bottom of the Funnel

The last piece of the smart selling puzzle requires salespeople to restructure their competences to accommodate for digital media. Whether it’s a discovery meeting, a video call, a presentation with multiple stakeholders or a negotiation meeting, selling online is not the same as selling in person.

Conversations are more difficult when the customer becomes a tiny window on the screen, as we can easily miss facial expressions and movements when we focus on presenting our content. In addition, our regular rhythm may be too fast for a video call, as lag compels us to leave some room between one argument and the next to allow for the customer to jump in.

Digital selling does not require new competences but, rather, an update on the traditional ones:


The greatest asset of many salespeople, empathy must be thoroughly updated and changed to work in an environment where emotional cues are conveyed through a tiny window on our desktop, such as when someone is presenting content. Shifting from affective (“see-feel-react”) to cognitive (shift perspectives, and imagine feelings) empathy is crucial to avoid the inevitable loss in nonverbal communication.


Salespeople must sustain their rhythm with prolonged pauses between arguments. Their speech should keep the customer alert and leave some room for him or her to speak; pauses are necessary because of delays in communication, which happens when WiFi connections come between the salesperson and the customer.

Needs Discovery

Smart selling relies heavily on insight-based sales methods. Customers are working from home, and their time is precious. Asking a lot of questions to assess the customer’s situation is risky in a digital environment.

Insight-based sales approaches stress preparation and a profound knowledge of the customer’s business to build competence and align on needs while saving time. In B2C sales, it can be more challenging, but even here, imagining the customer’s situation and figuring out what he or she needs, wants and fears helps salespeople be empathic and relevant, in their communication.


In some industries, where demonstrations are crucial for the sales process, smart selling seems like a daunting challenge — but it shouldn’t be. Learning to use a camera to create a digital walk-around of the car or to show a medical device, for example, can help bridge the gap.

Digital Skills

Learning how to use proficiently videoconferencing tools is crucial to smart selling. This skill does not only involve knowing the tool’s basic buttons and functions but also how to use them in conversations as well as when to use more advanced options, such as whiteboards, annotations and different view modes.

L&D professionals can leverage their sales and information technology (IT) colleagues as subject matter experts (SMEs) on these topics. In training, the key to success is rehearsals and role-plays. Salespeople can lose focus easily if digital skills training is too tool-oriented; scenario-based training and role-plays help them see these behaviors in action.

All in all, it’s an exciting time to be in sales training, with the need to update salespeople’s skills as quickly and effectively as possible. The success of our companies depends on it.