AI-Powered Sales Coaching: Hands-Off Virtual Training

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Increasing numbers of sales managers are turning over much of their sales training responsibilities to artificial-intelligence-powered sales coaching, which enables salespeople to continually practice their skills on photorealistic, virtual “customers” until they’ve forged the perfect pitch.

This novel approach to training can be especially effective with people who grew up with computer gaming and are accustomed to interacting with on-screen, computer-generated personalities that challenge them to think, strategize and “roll with” situations and reactions that are often extremely unusual or unexpected.

While the use of AI in sales training is still very new to trucking, there are a few industry players who are preparing to give the tech a try — or are at least open to the idea.

Joe Dysart


Ed Ackfeld, director of sales and program management at Yellow Corp., said the less-than-truckload carrier is working with Salesforce to bring its AI-powered sales training system onboard.

Dubbed Einstein Conversation Insights, the software uses AI to listen in on sales calls, analyzes what’s going on and then offer sales staff pointers on what it believes is working and what can use improvement.

“AI is going to play a significant role in our growth. As younger generations enter our sales force, the need to train faster has never been more important,” Ackfeld said. “In the LTL industry, the amount of information and technical data that a great salesperson needs to know is significant and necessary in order to be successful.”

Ed Ackfeld


Traditionally, that training has often required sales trainers from Yellow to travel to various parts of the country to bring new recruits up to speed on the company’s sales philosophy and techniques, according to Ackfeld.

But with an AI-based system, much of that traveling can be eliminated, he indicated.

Using AI, we’ll “be able pinpoint what part of the sales process an individual could use additional support with and offer one-on-one training virtually prior to a sales call,” Ackfeld said. “We used to say that it takes a year for a new salesperson to be highly successful in an LTL sales position. AI can ramp up the training and help professionals get there faster. Our goal is to get success time down to 60 days.”

Jennifer Karpus-Romain


Jennifer Karpus-Romain, executive director at the Transportation Marketing & Sales Association, also sees real value in AI-based training, as long as companies view the tech as a value-added component to polishing the skills of their sales personnel rather than a complete replacement.

“Adapting training to include AI allows sales representatives to use technology through their initial training, so then sales managers can focus their training efforts on more complex, out-of-the-box scenarios,” Karpus-Romain said. “When we think of AI and technology as a supplement — and not a replacement for activities — we can really start to break down how a business can have optimal performance.”

Geoff Muessig, executive vice president of Pitt Ohio Transportation Group, said he’s also open to the idea of using AI to help polish the pitches of salespeople.

But Muessig added that any AI system the company would consider would need to be highly customizable to ensure it would incorporate the Pitt Ohio approach to sales.

I’d … need to know from our salespeople that they’d like to be trained using AI.

Geoffrey Muessig, executive vice president at Pitt Ohio

Geoff Muessig

That sales style, Muessig said, works out to 80% listening to what a customer wants and 20% assuring the customer how Pitt Ohio can specifically fulfill those needs.

“I’d also need to know from our salespeople that they’d like to be trained using AI,” he added.

It makes no sense, Muessig said, to bring in AI training without buy-in from the sales force.

Pitt Ohio Transportation Group ranks No. 50 on the Transport Topics Top 100 list of the largest for-hire carriers in North America. 

Corporate Visions, a sales training company for business-to-business-focused industries such as trucking, said it has already added AI sales coaching featuring photorealistic “customers” that salespeople can practice pitching.

The move was a no-brainer, according to Tim Riesterer, chief strategy officer for the company, after it validated that AI sales coaching can bring many more salespeople up to speed simultaneously than traditional methods.

Corporate Visions uses Second Nature AI sales coaching software.

Tim Riesterer


“In the past, our expert consultants would assess a seller’s skills and document feedback manually. This is very effective, but many of our clients need to do this at speed and scale, getting thousands of reps proficient in days,” Riesterer said. “With Second Nature, we train the AI with the best examples of the client’s message delivery skills and it does the rest — capturing performance, measuring effectiveness and providing coaching.”

One of the major reasons why Second Nature and AI systems like it are turning heads is their emphasis on customization.

Instead of marketing their services as the be-all and end-all for any kind of sales right out of the box, the software makers work with company sales managers to tailor their software to incorporate the skills, approach, tone and other qualities of selling that a manager knows work best at his or her specific business.

For example, AI-powered sales coaching software for a company selling medical diagnostics software to neurosurgeons is going to be customized much differently than AI sales coaching software tailored for a business that sells bungee cords to amusement parks.

Either way, once the AI software is customized for a particular business, it’s simply a matter of turning the system over to the sales staff to work its magic.


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In practice, pitching with Second Nature is a lot like attempting to sell a product or service over a Zoom video call.

As a salesperson, you’re pitching to a “customer” on your computer screen, rolling out your best lines, monitoring what the customer is saying and studying how the customer is reacting to you so you can modify your pitch at any given time.

But unlike that live sales call on Zoom, the “customer” you’re pitching to using Second Nature and similar systems is actually an AI-powered, photo-realistic representation of a customer — a “virtual being” that has been programmed to react to your pitch in the same way a real person reacts.

So as you make your pitch to the on-screen ‘customer’ in an AI-powered sales coaching system, the same questions, comments and even dashes of skepticism that you’d encounter with a human customer are expressed and emoted by the virtual “customer.”

Multiple personalities can be created to simulate customers from across the demographic spectrum. Plus, multiple personalities can also be dreamed up to simulate character quirks, mood swings, unforeseen questions and similar character qualities, which are only limited in depth by the imagination of the company sales manager who customizes them.

Yet another powerful component of AI sales coaching: As you’re making your pitch to an AI-powered virtual customer, the system is also recording your every word, move and emotional cue — analyzing your performance, second-by-second, and using that analysis to report back to you on the overall quality of your pitch. The system will let you know how to improve on moments in your pitch that seemed weaker than others.

The result? Salespeople using AI sales coaching can practice with various AI-powered customer personalities over and over again until they have their pitches just right for every major personality type that their sales manager believes they’ll come across.

Plus, the 24/7 availability of these AI-powered sales trainers ensures that salespeople are able to train with these systems at their own pace and on their own schedules.

Sales managers, too, are finding that these systems are changing their day-to-day in very positive ways. By customizing an AI system to sell using the specific formula that works for their company, for example, sales managers find that they can “program once,” so to speak, and train infinitely.

Plus, sales managers looking to get a feel for how far a new hire has progressed no longer need to listen in on a live call or observe how a new hire performs face to face.

Instead, for a status report on pitching performance, a sales manager can simply say to a new hire, “Show me your best pitch on video so far.”

Using AI also means sales managers no longer need to deal with new hires or others who may react negatively to constructive criticism regarding their pitching ability — or feel that the sales manager is unfairly singling them out for criticism. With AI sales coaching, there’s no one to be angry with — only a standard to achieve.

Yet another major benefit of AI-powered sales coaching: The tech enables a sales manager to update an entire sales force on how to sell a new product or service by simply doing an update to the AI system and passing it along to the sales force.

Granted, polishing your sales chops by pitching to a robot may sound counterintuitive in a profession where the art of developing and nurturing a relationship is the beginning and the end of everything you’re trying to achieve.

But when you consider that the robot has the ability and sophistication to assess those relationship skills from every aspect imaginable, AI sales coaching begins to make more sense.

Joe Dysart is an internet speaker and business consultant based in Manhattan. Voice: (631) 438-1142. Email:

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