People > Processes: A Conversation with Jonathan Sherman, SAE at Pluralsight

By: Teresa Weirich

January 25, 2018

In our inaugural People > Process post featuring Melissa Gindling, AE at Levementum, we began to uncover the incredible work that frontline sales professionals do every day, which is to help their prospective customers and existing customers succeed in the complicated world of enterprise technology.

We continue on in our People > Process series with our second article featuring another unsung hero, Jonathan Sherman, SAE at Pluralsight, a technology learning platform that helps enterprises assess technical talent among their workforce so that they may continuously improve upon it, innovate faster, and measure success. Jonathan is no stranger to the world of SaaS and technology sales, having spent years in sales organizations such as ExactTarget, Domo, Localytics, and now Pluralsight. In our conversation with Jonathan, he shared his belief of how enterprise sales should always be mutually beneficial, and provided us with some very helpful advice along the way.

Add Value By Diagnosing Before Prescribing

Historically, the profession of sales hasn’t always been seen in the most positive light, especially as it pertains to retail-oriented situations, such as car dealerships or clothing stores. Some individuals may choose to lump all sales professionals into a single bucket, classifying the overall category as pushy and money hungry, providing no tangible value other than to facilitate a purchase. However, to Jonathan, the sales executive role is highly valuable and dignified and is accompanied by major responsibilities.

Jonathan shared that he was recently in a training session where the presenter reinforced that in enterprise sales, it’s the sales professional’s role to add value by seeking to understand the issue at hand before providing a potential solution. Similarly, in the medical world, a doctor would never greet a patient for the first time by informing them of their problem and then proceeding to write a medication slip. Instead, the doctor would patiently work through a series of questions, perform the necessary tests, rule out potential culprits and, after enough information has been gathered, make a diagnosis and write the prescription. While the side effects of prescribing the ‘wrong’ technology solution may not be life threatening, the role of the sales professional is not all that conceptually different from the doctor’s.

Do the Ordinary Tasks Exceptionally Well

It can be difficult for enterprise sales professionals to set themselves apart. According to Jonathan, many sales professionals in the enterprise tech arena really do strive to help their prospects succeed. One way Jonathan sets himself apart from competition and builds trust is by paying attention to detail on the little things. Rather than rushing through the tactical administrative tasks or matter-of-factly ‘outsourcing’ them to more junior associates, Jonathan aims to focus on them and emphasize them. For example, Jonathan sends follow-up emails after meetings, detailing who was present and what was discussed, as well as planned next steps. It’s little things like this that are often overlooked, but go a long way in terms of earning trust and building credibility with prospects and clients.

“No sales professional prepares to the full extent that they could. If I can be more prepared and follow-up after the fact better than the competition, it’s a pretty simple way to set myself apart and earn customer confidence at the same time,” said Jonathan.

Approach Enterprise Sales as a Mutually Beneficial Partnership

Jonathan explained that enterprise sales professionals have a dual responsibility: add value to the customer and deliver for one’s own company. From the first prospect meeting to the last signature made on the contract, the sales professional is the face of his or her company. He explained that it’s their responsibility to approach every prospect respectfully and valuably. If a prospect were to meet him for the first time at a conference or on the street, he wants that individual to want to learn more, to want do business with him—not out of obligation, but because of his credibility and the potential value he brings to the table as Pluralsight.

Jonathan strikes this balance of helping the prospect succeed while simultaneously honoring his own company in two ways. First, as it pertains to his role to prospects and current clients, he is the quarterback of the team. As an enterprise-focused sales professional, Jonathan infrequently takes a meeting on his own. Whether he’s hosting a discovery conversation or an onsite solution presentation, he has team members rallying along with him: solution engineers, customer success managers, marketers, executives, others. He explains this as a “multi-faceted approach to delivering value to large, complex organizations” and it’s this whole-team effort that lands squarely on his shoulders. He must coordinate and ensure that each individual is engaged, knows their role, understands the customer’s needs, and is an active participant in delivering according to plan.

Second, Jonathan also has an important responsibility to his own company, which is to deliver financial success. Balance is found between adding value to the prospect and adding value to his own organization. If a sales professional delivers success and value to his or her customers, then those accounts will grow. The end result is mutually beneficial for everyone involved.

In his final words of wisdom, Jonathan debunked the popular saying, “the customer is always right” by explaining his perspective:

“I don’t go along with the mentality that the customer is always right. But, if I have to prioritize, customer value always comes before my personal gain. Do I push it aside altogether? No. But each B2B relationship is ongoing with a series of steps that requires communication along with give and take. Some meetings, for instance, may deliver much more value to my prospects than to me, and that’s okay—it’s a natural part of enterprise sales. However, at renewal time or upsell time when the customer is realizing value, then I’m able to benefit as well.”


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    Teresa Weirich

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