How AI can help train sales teams (and where it can slow them down)

Posted April 18, 2024

How sales teams use AI for training and where it slows them down

Ever had that "aha!" moment a day too late? It's a common experience, especially for sales reps who realize they forgot to mention a crucial product feature during an important call. But unlike a casual chat, a slip-up like this can mean missing out on a deal.

Being prepared is about having the right answers at the right time. That's why we're leveraging advanced tools to transform how sales teams train and perform. As a leading AI sales platform, Outreach provides immediate guidance and insights, ensuring your team is always ready. Let's explore how the latest innovations in AI sales technology is changing the way teams approach sales training.

We’ll look at how exactly AI can help train your sales team in a bit but first, here’s how sales training has evolved over the years.

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The evolution of sales training

Presently, sales training focuses on skill reinforcement, process improvement, and personalized guidance for sales reps to succeed in their roles. But it wasn’t always like this.

Sales training in the 50’s concentrated on building direct customer relationships and had sales leaders teaching the art of persuasion as salesmanship. Then in the 70s, video training systems emerged and sellers were introduced to visual and interactive learning.

By the 80’s, sales training methods weren’t the only things evolving — customers and their needs did too. Sellers could only persuade buyers if they could match their product to one or more unique pain points. This not only demanded the sellers to have deep product knowledge but also meant they had to learn strategic questioning. It was here the SPIN selling model was birthed, followed by advanced sales models like Solution Selling and Consultative Selling.

Three decades later, Aaron Ross developed a framework that forecasted business growth based on results rather than activity metrics: The Predictable Revenue model. This model — which helped Salesforce add $100 million in recurring revenue — emphasized the importance of role specialization within sales teams and scalable sales processes for effective revenue generation.

Years have passed since Ross’ system revolutionized selling yet revenue generation is still dependent on the expertise of sales reps and how efficient sales processes at organizations are.

How AI works in sales training

Salesforce considers sales training to be one of the top five ways to drive efficiency and sales performance yet only 26% of sales reps have one-on-one weekly training sessions with their sales leaders. And while one session per rep may seem doable, it is nearly impossible to give personalized coaching to an entire team in one business week — while work is still ongoing.

Here’s how to leverage AI sales training to scale coaching and skill development within your sales team.

Role-playing simulations

AI sales training tools simulate lifelike interactions where sales reps can role-play pitching, active listening and strategic questioning to refine their sales skills.

Performance assessment

Some AI tools can analyze sales interactions to identify strengths and specific areas sales reps need coaching on.

Generative AI technology

With Generative AI technology like conversation intelligence software, sales coaches can effectively onboard reps and provide instant feedback while automating sales processes to ramp up seller productivity.

The benefits of AI in sales training

The traditional one-size-fits-all approach to sales training is quickly becoming a thing of the past. Thanks to AI, training programs are now as dynamic and individualized as the sales teams they're designed to help. In this section, we dive into how AI-enhanced sales training is transforming the way teams learn and succeed.

  • Personalized learning paths: One-size-fits-all training hardly works. AI sales training aligns learning with the strengths and weaknesses of sales reps at scale, motivating them to upskill and close their individual learning gaps.
  • Real-time feedback: Think of AI in sales training like a football coach. It guides your sales reps — like players on the field — teaching them how to navigate challenges and seize opportunities in real time, from handling customer objections to highlighting key product features that meet specific needs, or asking critical qualification questions before the calls wraps. 
  • Data-driven insights: AI breaks down big data sets into prescriptive and accurate information — trends, patterns, performance metrics and reports — that aid sales reps in making data-driven decisions instead of throwing spaghetti at the wall with their sales strategy.
  • Automated content recommendations: In between note-taking, listening to the prospect and finding upselling or cross-selling opportunities, valuable information can fall through the cracks. AI in sales training allows your reps hit the right chords with proactive recommendations without breaking concentration to find buyer-specific content.
  • Automated lead prioritization: Why spend time chasing a mismatched opportunity? AI can improve productivity and win rates by predicting which leads are more likely to convert after analyzing factors such as recent interactions, industry, their JTBDs and demographics, shortening the sales cycle for your reps.

Implementing AI in sales training

In a recent Gartner survey of 501 B2B sellers, only 25% strongly agree they complete all tasks assigned to them while also meeting company standards of high quality.

It might be tempting to bin your existing sales training stack for the “next best AI tool” on the market or even worse, pile on an extra tool with a steep learning curve because AI is the future of sales coaching. 

Sales leaders already know another tool isn’t the solution. Today, almost half of sellers feel overwhelmed by the number of technologies needed to do their work. This isn’t a mere annoyance — it’s the difference between hitting revenue targets and not. According to Harvard Business Review, sellers who feel overwhelmed by technology are 43% less likely to meet quota than non-overwhelmed sellers.

To make sure your sales reps are not spending valuable selling time learning to use an AI sales tool instead of training to close deals, consider these steps first.

Assess current training process

Find out how well your existing training process is working (or not). Take note of areas and tools that need improvement and map out how AI sales training can close the gaps. 

Research AI solutions

After troubleshooting your training process, determine what AI software best aligns with your sales training program needs: sales interaction analysis, product expertise, prospecting or feedback provision.

Define metrics and KPIs

What goals do you plan to smash with AI-powered sales training? List them out along with key performance indicators (KPIs) like larger opportunity sizes, higher conversion rates, or faster deal velocity, for example.

Integrate AI tools

Next, gradually integrate your new AI tools into your sales training program while making sure your sales teams are properly onboarded with guidance on tool usage and support throughout process implementation.

Analyze results and feedback

After a period of use, review your training tool’s AI-generated insights to analyze sales interactions, identify coaching opportunities and provide personalized feedback to help your reps drive sales performance.

Overcoming challenges with AI implementation

When used correctly, AI can increase your revenue and sales rep performance. In fact, 84% of US and UK-based sales leaders forecasted significant revenue increases after introducing new sales technology to their organizations and 80% of sales professionals attest to AI driving rep productivity.

Here are three common challenges with AI integration and how to solve them.

Data quality

AI leverages industry-scale machine learning models to serve up relevant information. However, synthesizing output from external data sources freely available on the open market corrupts data quality, resulting in biased sales predictions.

To combat this challenge, combine AI trained on your internal company and customer data — such as emails, meetings, and seller and buyer-based facts — with context and specificity to ensure data cleanliness, accurate predictions and minimized bias.

Integration with existing systems

Sales reps use an average of ten sales tools in their workflows. Adding more tools will hurt — work efficiency and cost-wise — if they don’t integrate with existing legacy systems or serve up data in familiar formats.

By identifying and sorting compatibility issues, sales managers can seamlessly integrate AI technology into their already existing tech stack as part of a complete system, not standalone tools.


Not every AI is made the same. And for sales leaders who want to capitalize on its productivity advantage, you need to identify what sets them apart. For example, large language models (LLMs) are available on the market. LLMs have been trained by data available on the open internet, and they can synthesize output based on that knowledge and training. But what they lack is the data that resides within a company, such as:

  • History-based context: Emails, calls, meetings, etc. that ensure relevancy from prior conversations.
  • Seller-based accuracy: Seller’s facts with recent updates, such as pricing and packaging, market position, or competitive offers.
  • Buyer-based specificity: Buyer’s facts like price quoted or quantity ordered that must be included for personalization.

Best practices for AI in sales training

We’ve looked at the game-changing advantages of AI sales training. Let’s review some practical tips and recommendations for effective implementation:

  • Start small and scale gradually: Begin by introducing AI in a small, controlled aspect of your training to see how it integrates and impacts results. As you gain confidence and understand its benefits, you can gradually expand its use across different areas of your training program.
  • Integrate with existing tools: Ensure that the AI solutions you adopt can seamlessly integrate with your current sales tools and platforms. This promotes a smoother transition and helps maintain continuity in your sales processes.
  • Focus on continuous learning: AI is continually evolving, so it’s crucial to keep your training programs up-to-date with the latest AI developments and techniques. Encourage ongoing learning and experimentation within your team.
  • Measure and optimize: Regularly track the outcomes and effectiveness of AI-enhanced training. Use these insights to tweak and improve the training methods, focusing on areas that show the most significant potential for improvement or that need additional support.
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Conclusion: Embracing AI solutions for sales teams

So, should your sales team embrace AI sales training solutions? The short answer is: yes. The evolution of AI in revenue organizations presents both challenges and opportunities. While predictive AI has become fundamental in modern sales tools for forecasting outcomes, generative AI technologies like GPT offer new potentials, especially as "co-pilots" in sales tools. These innovations can automate routine tasks but their potential to elevate sales strategies is just beginning to be tapped.

The question now is: Will your business simply adapt to AI, or will it harness these advancements to drive superior sales results? Discover how Outreach, our intelligent AI-powered platform, not only provides a detailed overview of your sales pipeline but also leverages both predictive and generative AI to empower your team, transforming insights into successful deals and keeping your business competitive.

Request a consultation to discuss how Outreach can help your team, or take a self-guided tour to get a preview of how to coach and improve your team's performance directly in the platform.


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