Upskill Your Salespeople to Outsell the Competition

Since the COVID-19 pandemic, a myriad of things have changed in the B2B selling environment. Digital transformation has exploded. Buyer journeys have rapidly transformed and become more complex. Disruptions from supply chains to working environments to regulations and restrictions continue to ebb and flow.

It is a tough time to be a salesperson. Suddenly, a once-leading salesperson may be struggling with selling in a hybrid environment — in-person, virtual and blended. Another might not have the right sales enablement tools to make the best virtual impression on a buyer. Others yet might feel disengaged, uncertain, unable to find or access the right tools to help them excel at differentiated value selling.

Now more than ever, salespeople need the support of their organizations. And businesses need to hold tight to a fledging workforce to avoid skilled staffing shortages.

During the Great Resignation in 2021, retention bonuses were the No. 1 tactic used to retain employees in selling organizations. In 2022, though, there is becoming a greater focus on long-term strategies to keep valuable people working for your organization — including employee upskilling programs and increased sales enablement and training. In a McKinsey & Company research report, in fact, when B2B leaders were asked which are key concerns for their organization, the top answer was for collaborative tools, guides, training and operating norms. In other words, enablement, training, and formal processes and alignment.


Employee upskilling means increasing the competency in a skill or behavior to increase performance in a current role or to prepare an individual for a future role. For salespeople, upskilling translates, then, to sales enablement and training. Not only should every organization aim for a formal sales enablement program, the current fluid market demands extra support and new skills to meet the new responsibilities of sellers and the changing needs of buyers.

Additionally, when organizations invest in their people, they also reap the benefits of employees who are more engaged, who become higher skilled for your specific organization and who want to stick around. The retention benefits are substantial: According to McKinsey & Company, “When a sales organization implemented a mentorship program that helped their frontline with career pathing, they saw a double-digit increase in retention percentage of salespeople.”


In the age of rapid digital transformation, selling organizations have a lot of options for enabling and training salespeople for upskilling. One of the most effective ways remains through internal- and external-facilitated instructor-led programs.

Internally, mentors can support employees with consistent feedback, reinforcement and accountability. The most effective leaders at this take on the Chief Reminding Officer approach, knowing how to pick the most important spots of training and how to reinforce these consistently for real change.

According to leadership and front-line professionals alike, employing an outside resource offers focused expertise as well as credibility that overcomes internal oversights and politics. To learn more about the power of Mereo sales enablement and training programs, explore the Pitney Bowes success story.

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