AI sales training tips, benefits and strategies for SMBs

AI Sales Training Tips for SMBs

AI improves sales training by providing personalized coaching, real-time feedback and data-driven insights.

With so many AI-powered sales tools available, SMB leaders have a wealth of options to enhance training. The challenge is finding the right fit and ensuring strong adoption by the sales team.

By the end of this article, you’ll understand how AI supports sales training. You’ll also know which tools to use and how to ensure seamless adoption.


How AI can support sales training (and which tools to use)

Artificial intelligence (AI) transforms training to provide sales reps with the skills, resources and ability to confidently close deals.

It delivers personalized coaching, provides real-time feedback and identifies skill gaps. Customizing learning experiences for each rep accelerates skill development and boosts sales performance.

Here are some ways AI automation enhances sales training, along with the best AI tools to support each approach.

Improve sales performance

AI can track key performance indicators (KPIs) and identify patterns. These insights help managers make data-backed decisions about training priorities.

The software analyzes sales call transcripts, email response rates, CRM data and more. It uses this data to identify skill gaps and areas for improvement.

For example, AI might analyze CRM and detect that leads often drop off late in the customer journey. This discovery could signal a need for more training on closing techniques.

Tool recommendation: Pipedrive’s CRM streamlines sales pipeline management. It optimizes lead tracking and automates the sales process, ensuring all leads move through the pipeline.

Pipedrive’s AI Sales Assistant highlights areas for improvement in sales activity. It monitors team activity, analyzes lost deals and provides insights into individual performance. These insights help you customize training to address specific needs.

AI sales training Pipedrive team performance


Say that the system notices that sales dip due to delays in follow-up after initial contact.

This information allows you to tailor training to ensure reps don’t miss follow-up deadlines. This training might include:

  • Improving how they prioritize tasks

  • Making sure they set reminders for follow-ups in your CRM

This targeted approach to training topics helps improve performance in key areas, ultimately boosting sales.

Note: Pipedrive offers a suite of powerful AI features to improve your sales process. Its AI email writer crafts personalized messages, while smart summarization and deal insights help you easily track progress.

The platform also integrates with third-party AI integrations via the Pipedrive Marketplace. Integrations include Engage AI (automating lead nurturing) and Overloop AI (optimizing outbound campaigns).


Create sales simulations

Learners can engage with AI chatbots that simulate real-world customer interactions. These conversations allow reps to practice handling sales objections and closing deals to refine their skills without the pressure of real-world consequences.

The chatbots use conversational intelligence (natural language processing and machine learning) to create responses. The software adapts its responses based on the rep’s input.

For example, a rep might practice addressing sales objections about pricing. The chatbot responds, mirroring real customer concerns. At the end of the conversation, the chatbot could then offer valuable feedback to improve the rep’s approach.

Here’s how this conversation might look:

Sales rep: “Our product may seem a bit pricey, but it offers significant value in the long term.”

Chatbot (customer): “I understand, but my budget is really tight. Can you justify the cost for me?”

Sales rep: “Absolutely! The investment pays off by improving your team’s productivity by 30%, saving you much more in the long run.”

Chatbot (customer): “That sounds promising. How quickly can I expect to see results?”

Sales rep: “Typically, within the first quarter, you’ll see measurable improvements, especially in time-saving and efficiency.”

Chatbot (customer): “Okay, that sounds more reasonable now. Let’s move forward.”


You can tailor these simulations to different customer personas, objections and sales scenarios. As a result, reps receive targeted practice in handling specific situations.

Tool recommendation: Second Nature is an AI sales role-play software. The system helps sales teams improve their sales skills through interactive conversations with a virtual sales coach.

AI sales training Pipedrive Second Nature


The generative AI simulates real-life sales scenarios and provides real-time feedback on tone, clarity and persuasion. This feedback helps reps improve sales pitches, handle objections and build confidence.

The software is also easy to use, meaning users don’t need extensive training to get it up and running.

Analyze sales conversations and offer AI-powered sales coaching

AI sales coaching platforms analyze real sales conversations to identify strengths and areas for improvement and provide feedback. This targeted feedback helps sales reps improve communication skills and close more deals.

The software monitors pacing, tone, word choice and response patterns.

For example, during a sales call, an AI tool might pinpoint areas where the rep didn’t address customer objections. The tool would then offer tips to improve future interactions.

Here’s how the feedback might appear:

“When the customer expressed concern about the product’s complexity, you quickly moved to a different topic. Next time, take a moment to explain how the product’s features can be easily adapted to their needs, addressing the concern directly before proceeding.”


The salesperson can then apply this feedback to improve future customer calls.

Tool recommendation: Gong.io is an AI-powered revenue growth platform that records and analyzes sales calls. It provides insight into customer sentiment, deal risks and coaching opportunities.

AI sales training Pipedrive Gong.io


Gong also transcribes your sales calls, allowing you to search conversations. As a result, you can review critical moments in more detail, allowing for deeper reflection on the conversation’s context, tone and word choices.

Transcripts also help reps better understand the nuances behind the AI’s recommendations.

Strengthen face-to-face conversation skills

Video-based AI platforms allow sales reps to practice their pitches with an AI avatar. The software provides feedback on tone, clarity and persuasion skills.

For example, a rep might rehearse a sales demo and receive instant feedback on pacing and word choice. Practicing helps the rep refine their delivery and build confidence before real customer interactions.

Video AI also evaluates body language, facial expressions and overall presentation abilities. These skills are critical in building rapport and trust with customers.

Tool recommendation: Avarra is an AI-powered tool that offers video-based role-playing simulations. It uses AI to create realistic customer interactions.

Sales reps can practice handling scenarios like overcoming objections or pitching products. The AI analyzes the sales rep’s performance, providing feedback on key aspects like tone, clarity and confidence.

AI sales training Pipedrive Avarra


Avarra uses meeting recordings, sales transcripts and product materials to create sales simulations. It also creates customer personas, enabling reps to practice engaging with various audience segments.

Design personalized learning paths

AI training tools can recommend specific training programs and content for individual sales reps. This approach helps reps focus on performance issues they struggle with and bridge any skill gaps.

For example, if a rep struggles with handling objections, AI creates a tailored training program. The program includes content to upskill reps in active listening and empathizing with customers’ concerns.

The software typically allows sales leaders and managers to input prompts into the system. Prompts could include sales performance reports, conversation transcripts or buyer personas.

AI then tailors training programs to each salesperson’s strengths and weaknesses.

Tool recommendation: Easygenerator is an AI-powered tool that simplifies eLearning content creation. It provides smart suggestions, content recommendations and ways to optimize learning materials.

AI sales training Pipedrive Easygenerator


The platform helps create personalized training experiences. Simply upload your sales documentation, use cases and reports, and AI will generate training materials – saving time and ensuring sales reps receive relevant, targeted training.

5 best practices for implementing AI sales training tools

Once you decide to use AI sales training, take steps to ensure it has an impact. The following best practices will help you integrate AI seamlessly to support your sales teams in their work and career progress.

1. Align AI training with business goals

Aligning sales training with business goals helps your team focus on skills that drive company success.

For example, if one of your sales goals is to improve win rates, prompt AI to design training on closing techniques. If you want to increase upselling, prompt your role-playing tool to look for and provide coaching around missed upsell opportunities.

Here are some ways to align your training efforts with your business goals:

Clarify your business objectives

Define specific sales goals, such as increasing conversion rates, improving customer retention or shortening the sales cycle.

Identify skill gaps

Use CRM data, performance reviews and AI-driven insights (like sentiment analysis from sales calls) to pinpoint skills your team is lacking.

Match training content to key objectives

Provide AI sales tools with the prompts and data to create training programs and practice experiences that align with business priorities.

For example, if your goal is to expand market share, add competitor data, customer pain points and past sales wins to your AI software. This will train the AI tool in ways to coach or interact with learners.


When setting sales goals and identifying skills gaps, it helps to have a well-organized CRM. A structured sales CRM has the most up-to-date information to provide AI with reliable data for analysis.

For example, Pipedrive’s CRM helps you pinpoint where deals stall, which reps struggle with follow-ups or how different sales stages impact conversion rates. AI can then use this data to create personalized training that supports business success.

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2. Ensure team members know how to use the software

Train team members on how to use the AI training systems. When reps can confidently navigate the platform, adoption and sales performance improve.

Picture this: you choose an AI system to track client calls and provide feedback.

Your sales team doesn’t know how to use the software, so they’re less likely to use it. Company sales performance suffers as a result.

Now picture this: sales reps receive clear instructions on using the software.

Confidence in using the system means your team will be able to take advantage of the feedback. They learn more quickly, leading to faster skill development, more effective client interactions and better sales team performance.

Here are some ways to ensure sales reps can use AI systems:

  • Provide interactive onboarding. Walk reps through key features with hands-on sessions. That way, they experience the software firsthand and understand its capabilities in real scenarios.

  • Offer live demonstrations. Organize live sales demos with the software provider. Show sales reps how to use the AI tools to analyze calls, track progress and implement feedback in real time.

  • Create easy-to-follow guides. Share provider resources or develop your own reference guides and video tutorials to show how to use the system in simple steps.

Provide ongoing support for AI systems to ensure reps use them effectively and address any issues. Track usage and sales performance and offer regular check-ins to touch base with employees.

3. Integrate real-world scenarios into your AI training

Use AI-powered simulations and role-playing exercises that mirror real sales situations. These exercises let new reps practice and improve their skills in a safe environment.

For example, use AI chatbots to simulate objections from a prospect. Reps can then practice responding and adapting before talking to actual clients.

Here are some ways to incorporate real-world situations into your AI training:

Choose the right simulation format

Select text, voice or video scenarios based on what best simulates real sales interactions.

For example, if your team communicates with clients over the phone, use voice-based systems. If email is more common, choose text-based chat simulations.

Incorporate buyer personas

Add your ideal customer profiles to the AI system. Ensuring simulations reflect the specific characteristics, needs and behaviors of your target customers will make the training more relevant and realistic.


Make sure that the AI software also designs simulations around tricky situations.

Sales professionals must know how to handle situations like demanding clients or complex objections. Practicing these skills helps them build resilience and gain confidence in managing obstacles during actual sales calls.

4. Customize training for your sales team

Use AI to create personalized training plans. Tailoring the training helps individual reps develop the skills they need to increase sales.

For example, if a rep is good at lead generation but struggles with closing, AI can suggest content and training modules on closing techniques and objection handling to help them strengthen that area.

Consider these tips for customizing training with AI:

  • Analyze individual performance. Use AI to assess each rep’s strengths and weaknesses based on metrics like conversion rates, call data and customer feedback.

  • Incorporate role-specific training. Tailor content to the specific roles in your sales team, from lead generation to account management, ensuring relevant skill development.

  • Leverage CRM data. Integrate CRM reports and insights to focus training on customer-facing situations your reps encounter most, such as handling objections or closing deals.

After creating training plans, track rep performance. For example, monitor their close rates, customer satisfaction or response times during calls. These insights identify skill gaps and allow you to adjust training programs as needed.

If a rep has mastered cold calling but struggles with follow-up emails, AI can shift the focus to crafting effective email templates and tracking response rates, helping the rep improve in that area.

5. Encourage human-AI collaboration

While AI can analyze data and offer valuable insights, it can’t understand emotions and context. Combining AI with human input covers all the bases, providing the best possible training for your sales team.

Say a sales rep struggles to notice a client’s emotional cues during a call, leading to long pauses and abrupt shifts in the conversation’s tone. AI detects these traits and flags the issue, but it can’t identify the reason behind it.

A human coach, however, can see emotional cues. They can offer guidance on conversational intelligence and explain how to adjust communications to better connect with the client.

Here are some ways to effectively combine AI and human coaching:

Review AI insights before coaching sessions

Analyze AI data to understand the rep’s challenges. Use these insights to inform your advice and guidance to each sales rep.

For example, if AI flags a team member’s struggle with relating to client concerns, you can recommend training on active listening and validating concerns to improve rapport.

Incorporate AI feedback into live coaching

Use live AI feedback to address issues as they happen.

For instance, in an AI role-play, the software might pinpoint when a rep struggles to handle objections. The sales manager can immediately intervene, offering real-time guidance. The rep can then immediately apply the feedback, leading to faster improvement and stronger retention of the new skills.


Final thoughts

To maximize the benefits of AI in sales training, align the technology with your business goals, ensure team members are comfortable with the tools and combine AI insights with human coaching.

Incorporate key customer data into your sales training with Pipedrive’s AI-powered CRM. Access valuable customer insights (including demographics, needs and preferences) to inform and enhance your training efforts.

Sign up for a free trial today.

Driving business growth

Driving business growth