Coached by a Bot, Closing Like a Pro: AI’s Role in Sales Enablement
by Jenny Ayers, CPTM
Economic uncertainty, supply chain issues and changing customer expectations have had a significant impact on sales teams, making it more difficult for reps to meet their quotas. In fact, studies show that the majority of sales reps have struggled to meet or completely missed their quotas in recent years.
To meet the needs of today’s market, training professionals are utilizing artificial intelligence (AI) to train, coach and enable their sales teams. According to Salesforce’s State of Sales report, high-performing sales teams are nearly twice as likely to use AI as low-performing teams. From real-time role-play simulations to workflow automation in customer relationship management (CRM) tools, AI is proving to be transformative for sales — not by replacing human salespeople, but by supporting their ability to connect, communicate and convert.
From Prep Work to People Skills
According to a CGS report, 82% of organizations now prioritize human-AI collaboration skills. As AI takes over repetitive tasks like data mining, proposal writing and CRM updates, the human element of sales becomes even more essential. Instead of spending hours researching accounts and prepping strategy decks, sales reps are increasingly expected to synthesize insights in real time, listen actively and steer high-impact conversations.
“The best salespeople are going to excel at human skills like empathy, trust-building and creative problem-solving,” says Doug Stephen, president, CGS Immersive. AI helps free salespeople from administrative tasks, but success depends on their ability to listen and guide customer conversations.
Nick Valla, co-founder of Valla Group, explains, “Traditionally, sales training focused heavily on research and account planning. Now, we’re using AI to do those things, so training should focus on how to take that data and guide the conversation, what key things to listen for and how to pivot across the buy-sell process.”
AI tools like Salesforce Einstein automate prep work, summarizing company data, drafting emails and forecasting deals, freeing up reps to focus on the human side of the sale. This focus on execution strategy over manual prep is changing how we define sales effectiveness, and it requires new training programs to match.
AI Role-Plays Are Replacing Peer Practice (For the Better)
Reps know role-play improves performance — they just don’t want to do it. “We found that while 67% of our customers believe role-play is critical to success, only 35% like doing it — mostly because they don’t want to be embarrassed in front of peers,” says Stephen.
Enter Cicero, CGS’s AI-powered role-play engine that lets reps practice scenarios safely, privately and at scale. Cicero’s AI personas can simulate specific buyer types, drawing from CRM data to mirror real-life prospects, and provide instant, unbiased feedback. “One of our clients uses Cicero alongside Salesforce to simulate pitches to individual physicians, drawing on specific notes from the CRM to mimic each doctor’s personality and objections,” Stephen says.
AI makes practice more accessible and psychologically safe. And with the AI-generated transcripts and scores, managers can review sessions and coach more efficiently and effectively.
Reinforcement, Retention, and Real-Time Coaching
Sales reps need to practice repeatedly, safely and with real-time feedback. “AI’s role is to help you cultivate skills through repetitive role-play and reinforce them with on-demand coaching tools, shortening the sales cycle,” Stephen says.
AI allows sellers to repeat scenarios until they’re confident. Combined with tools like Gong and Salesloft, reinforcement becomes part of the workflow rather than a separate event. That’s key for busy reps, and even more so for trainers trying to prove return on investment (ROI).
Funnel Clarity is building an AI-based coaching bot for this very reason. “It uses years of our content to coach reps in real time,” Snyder says. “If you’re walking into a meeting and need a refresher, the bot gives you the information right there on your phone.”
Tools like Gong and Chorus analyze live sales calls to provide feedback on tone, pacing and customer engagement. When combined with platforms like Salesforce Einstein, which automates proposal writing and forecasts deal success, these tools create an integrated ecosystem for continuous improvement.
Enabling Sellers With Context That Counts
AI’s role in sales enablement isn’t just about role-play and automation, it’s also about helping reps stay informed. According to Valla, the best use of AI goes beyond automation to information. “The future is really going to be looked at through the lens of the buying experience and using this data to intelligently guide that forward,” he says.
That means training reps not only on how to use these tools, but how to act on the insights they provide. Tom Snyder, founder of Funnel Clarity, envisions sales enablement platforms using AI to search an organization’s deal history for parallel scenarios, turning past wins into personalized coaching opportunities. “Salespeople don’t have time to go through 2,000 records in the CRM, but AI can do it in an instant and can give exact examples of other salespeople’s experiences with specific scenarios or clients.”
By pairing AI-enabled insights with targeted coaching, L&D can help sellers move beyond theory and into practice, delivering the right information at the right time.
Sales Managers Need Training, Too
Sales trainers aren’t the only ones navigating AI adoption. Stephen warns that sales managers — often overlooked in enablement plans — must also be equipped to coach using AI data. “These tools can analyze conversations for tone, pacing and engagement,” he says. “But if managers don’t know how to read that data, they can’t coach effectively. They must be trained to interpret the results from these tools to ensure salespeople move in the same direction as the company,” he says.
For those concerned about AI replacing human coaches, Valla explains, “It’s not about replacing these roles — it’s redefining how they operate.” Traditionally, salespeople are coached on behaviors, but with AI role-play and its ability to address behaviors in real time, sales coaches and trainers will need to shift their focus to making the AI-generated data actionable. “We didn’t have all this data before. So now, we have to teach salespeople to use this data in their conversations, which is a just a new set of skills.”
When sales managers understand AI data and use it to coach, they reinforce behaviors in real time and boost performance across the board.
Streamlining Workflows, Not Stacking Tools
As more platforms race to add AI functionality, tool fatigue is real. One mid-size tech company Valla works with counted more than 80 different tools in their sales tech stack.
That’s why integrated, workflow-driven tools are becoming the gold standard. For example, Valla’s team developed an AI-guided selling engine that sits inside Salesforce, pulls external data, builds account plans, and even suggests outreach strategies. “It’s not about one use case,” he says. “It’s about connecting workflows to redefine how sellers operate.”
For L&D, that means stepping back and evaluating the tech stack. Are the tools reinforcing the right behaviors? Are they generating data coaches can actually use? If not, it might be time to recalibrate. Instead of layering more tech on top, L&D should focus on building an ecosystem.
The Bottom Line
AI adoption should be strategic. L&D leaders need to validate each tool’s output, ensure data privacy, and most of all, explain why the AI is suggesting a specific next step.
As for getting buy-in, Stephen advises, “Growth is one of the biggest motivators of the sales team, and if they know that by using these tools there is a way to really surpass their targets, they’re going to adopt it.”
When used right, AI doesn’t replace the human side of selling, it enhances it. As Snyder puts it, “This is a phenomenal tool. Instead of being afraid of it, let’s be creative and think about all the things it can do for us.”
The companies that adopt AI with intention are already seeing the payoff. From smarter conversations to more efficient workflows and scalable coaching, AI is not just enhancing training — it’s reshaping the sales profession itself.