Indulge us for a minute while we share some statistics about pickleball. It has been the fastest-growing sport in America for four consecutive years. Participation soared to 19.8 million players in 2024 — an increase of more than 45% from the prior year. The number of players has grown 311% over the last three years, and participation is now highest among 25-34 year-olds.
We’re not here to urge you to pick up a paddle (though the game is “lit,” as that younger cohort likes to say).
Rather, pickleball’s popularity has key aspects in common with B2B sales. There are important lessons that sales managers can learn via a brief dissection of the current state of pickleball.
Spend 15 minutes watching doubles at any multi-court pickleball facility and you’ll likely see a wide range of play. On some courts, points last only three or four shots. Players are uncertain of themselves and are reactive instead of proactive. On other courts, players may hit the ball 20 or more times on one point. There will be a wide array of shots, and players seem to instinctively know where the next shot is going. They stay calm while making quick decisions and think one or two shots ahead of the one they’re making. In short, every action is done with intent.
Sales managers, does this sound similar to the variance among your reps as they move through the sales process?
Pickleball’s popularity is attributed, in large part, to the fact that it’s easy to learn and relatively easy to become halfway decent at it. What you haven’t seen when you watch high-level pickleball players execute with confidence and conviction are the hours of practice they put in to produce that performance.
Huh… Sounds like B2B sales.
The 3.0 to 3.5 pickleball players (most players rate themselves on 1-to-5 scale) are the equivalent of salespeople who do well enough to stay employed, but usually miss quota and can’t seem to improve. The 4.5 and 5.0 pickleball players are akin to sales superstars who regularly exceed quota, compete against themselves as much as anyone else, and grab every opportunity to hone their skills so they can perform even better.
It’s fun to play pickleball; it’s not as much fun to drill. But drilling is where the improvement occurs.
It’s fun to make a sale. It’s not as much fun to practice your discovery techniques, role play or review why past prospects were lost to a competitor. However, those habits are what lead to hitting and exceeding quotas.
Practice Makes Profits
Asked during a webinar what produces the biggest gap between stellar and so-so sales reps, David Ashe, director of sales development at sales enablement provider Allego, quickly replied, “Coaching. People aren’t getting enough help. Most sales reps feel they can do it on their own, but as leaders, we should be trying to help as much as we can.
“I run an inside sales team that is responsible for booking meetings for AEs to close deals. For the greener people that I’ve worked with in enablement, the biggest gap was giving them opportunities to practice, especially if you have a remote team,” Ashe added. “Just like with any sport or playing an instrument, you need to practice, practice, practice before you go out there and do it live.”
Most sales managers understand the importance of continuous learning, but for whatever reason — or for a whole host of reasons — they become resigned to forging ahead with training that is mediocre at best.
In research by Allego and RAIN Group, 67% of organizations rate their sales training as moderately effective or worse.
According to the research, the one-third of organizations that rate their sales training as extremely or very effective:
- Boast a nearly 12% lower turnover
- Are nearly five times more likely to agree with the statement that their onboarding gets sellers productive
- Are 5 times more likely to agree their training prepares sales reps to succeed.
So, what keeps the 67% of organizations that are sour on their sales training from joining the 33% that attribute much of their sales success to effective training? In a word, says RAIN Group CEO Scott McDonald, intent.
“Sales training needs to be as intentional on Day One as it is on Day 365. This requires a massive commitment from the organization’s leadership to see it through with intentionality,” McDonald said. “As is true in most organizations, priorities shift frequently, and without disciplined reinforcement tools and measurements, focus shifts.”
A key factor that determines successful sales skill and behavior adoption is an organization’s willingness to invest in a transformative process, not just isolated sales training events, McDonald said.
The Shift to AI-Driven Training
The organizations that are intentional about developing a top-level onboarding process and superior ongoing training will perform significantly better than competitors. That hasn’t changed. What has changed — what is currently changing dramatically — is how sales training is delivered, and it’s mostly a result of advancements in the past decade in artificial intelligence.
Although the origins of AI research date back to the 1950s, it has been less than a decade that AI has had a broad impact on business operations. The introduction of ChatGPT in 2022 brought AI use in business to the forefront for business leaders. It kick-started an AI arms race that has C-suites globally rushing to figure out where to invest in AI and how to train workers to adopt it.
Whether AI lives up to its current hype remains to be seen. In an article published earlier this year in MIT Sloan Management Review, educators David Wingate, Barclay L. Burns and Jay B. Barney argued that AI technology, like personal computers, internet access and blockchain technology before it, will become so ubiquitous that it cannot provide a significant competitive advantage.
“By definition, if everyone has access to the same technology — even if it is new and valuable — it may move the market as a whole but will not uniquely advantage anyone,” the authors state.
“Far from being a source of differentiation, artificial intelligence will be a source of homogenization. Part of AI’s value is that it is digital, and therefore it is fundamentally copyable, scalable, repeatable, predictable and uniform,” they add.
Data Doesn’t Lie
RAIN Group’s research on organizations that rate their training as extremely or very effective compared to those that say their training is only moderately or not at all effective reveals some important differences.
93% of highly effective training organizations incorporate in-person, instructor-led methods, compared to 65% of less effective programs. Additionally, the organizations with effective training leverage virtual instructor-led training and virtual self-study as part of a blended approach.
Highly effective training organizations offer more learning reinforcement activities (1.5x), online coaching (1.4x) and role-play and simulations (1.3x) compared to organizations with less effective training.
Organizations with effective training are 2.2x more likely to have strong leadership support for continuous learning and 5.2x more likely to provide resources that prepare sales managers to motivate and coach their teams.
55.7% of organizations that rate their training highly encourage mentoring or coaching on a regular basis, while only 19% of organizations that aren’t pleased with their training do so.
The company built a library of “golden demos” — actual recordings of top-performing reps whose discovery conversations consistently converted high-value customers. They compare each rep’s sales calls to these gold standards. AI scores each call and recommends areas for improvement, providing reps instant and consistent feedback.
Podcaster, author and NYU Business Professor Scott Galloway, a self-professed “AI optimist,” says it’s not AI that will take people’s jobs, but people who know how to use AI most effectively. “The people who know how to incorporate AI tools into their jobs are going to make much more money.” They will become “ninjas with these weapons,” Galloway told an audience of HR leaders at the UNLEASH World Conference in Paris in October.
B2B sales leaders take note. If AI technology isn’t incorporated into your training process yet, it better be in 2026. David Ashe of Allego says early adopters of AI for sales training are using the technology to build personalized, on-demand training courses, create and instantly score role play, evaluate real conversations with prospects, and develop reinforcement material based on content covered in all these exercises.
Redcar is a Silicon Valley startup that provides an AI-driven platform for automating and scaling B2B sales outreach. Er Jia Jiang, Redcar co-founder and vice president of growth and operations, told SMM the company uses its own SaaS platform to train its inside sales team.
“Think of AI as a smart intern. Interns are flexible and adaptable, and there is a lot of room for customization. It’s all about how you manage them,” Jiang said. “Sales reps need to be trained how to manage AI. In short, they need to get the AI to execute, review their work, and then re-coach the AI.”
The Redcar platform, she said, allows sales teams to essentially create an AI sales coach/agent for each individual rep. At the same time, AI takes much of the load of coaching off sales managers’ plates by doing things such as reviewing and critiquing role play and actual calls, creating training content (quizzes, videos, etc.), and developing skills training and product support material. Equipping each sales rep with their own AI agent will help them become “superhuman.”
Tal Paperin, a business growth consultant and executive for hire who works from Israel, told SMM that when he was hired last year to lead revenue growth at a Florida-based medical software provider, one of his first projects was to use AI to turn copious amounts of product information into a training manual for his expanded inside sales team.
In many ways, the instant access to data and analysis that AI provides has shifted training from a task that is separate from selling to an everpresent component of the sales process, Matan Korin, vice president of sales at Ecoline Windows in Canada, told SMM in an email exchange. “Tools like Lessonly, HubSpot Academy and Seismic help us integrate learning directly into their work rather than treating it as a separate, isolated task,” he said.
Human/AI Combo: A Magic Mix
As with sales itself, AI tools can greatly enhance training, but a human element should always be part of coaching. Allego partnered with Carmen Simon, a cognitive neuroscientist and the chief science officer at Corporate Visions, on a study to determine whether salespeople respond better to sales training that is delivered through AI or when it is delivered by a human.
Forty-eight B2B sales professionals were asked to simulate a discovery call with a prospect who was considering purchasing a training platform. Half the participants received feedback from a human and half received feedback from an AI assessment tool. All participants knew ahead of their 30-minute experience which group they were in.
The hypothesis going into the study was that coaching delivered by a human would likely offer more social presence, emotional warmth and reciprocal responsiveness, which are known to affect motivation and memory encoding. Those receiving feedback from AI, it was thought, could feel the training was clearer, more consistent and efficient.
It became clear that sellers don’t respond the same way to human and AI feedback. Key findings from the study include:
- Participants expecting AI feedback showed more mind-wandering but higher neural synchrony, while those expecting human feedback felt more relaxed,motivated, and emotionally aligned.
- Sellers who received feedback from the AI coach remembered 50% more content after 48 hours than those who received feedback from a human coach.
- Human feedback, on the other hand, triggered more emotional engagement, even if it didn’t improve
“The most successful sales training programs will blend the strengths of both approaches, tailoring coaching to the needs of individual sellers and the realities of modern sales environments,” the AI vs. human training report summarized.
“AI coaching will not replace human coaches or sales managers,” the report continued. “Rather, it serves as a scalable, structured and low-pressure complement to the relational strengths of human feedback. When used together, these modalities reinforce each other.”
How to implement AI into sales training and the sales process itself was the focus of last spring’s Gartner CSO and Sales Leader Conference in Las Vegas. In his opening-day keynote address, Gartner for Sales Vice President Analyst Dan Gottlieb said, “It is a really rare time to be a leader in sales because this epic profession is going through an awakening, and all of you are the chosen leaders to guide its transition.”
The AI transformation will occur in days or weeks, not years, Gottlieb stressed, adding that companies that fail to develop a formal AI for sales adoption strategy and that fail to hire with AI skills in mind will be left behind.
Gottlieb urged sales leaders who argue their company is not AI-forward to take matters into their own hands and at least make their departments more AI-focused. AI-driven training platforms are a great place to start.
“This is your moment to get that swagger and set the tone to chase a new productivity frontier,” he said. “Improvement doesn’t come drastically or immediately. But if you start today, by 2027, you will realize exponential improvements of revenue, cost of sales and AI maturity. Can you imagine if you wait three years to start this?”
