Sales enablement

Five Best Practices for Mastering Software Sales Training

The CloudShare Team

Sep 23, 2024 - 4 min read
Best Practices for Mastering Software Sales Training

In a perfect world, you wouldn’t need to train your salespeople. They’d know how to do everything right out the gate. But we don’t live in a perfect world — while new additions to your sales team might understand the basics of Software-as-a-Service (SaaS) sales, they’ll still need coaching on the specifics of your business, product, and market. 

Let’s talk about what that involves by going over a few best practices for developing a winning sales training program. 

Pay Attention to Your Sales Training Technology

Even the most impactful and insightful training materials are ineffective if they’re not delivered properly. The right sales training platform therefore makes a huge difference to your training program’s effectiveness. We recommend looking for a solution that is: 

  • Cost-effective, with transparent, usage-based pricing. 
  • Customizable, allowing you to create content tailored to different responsibilities, roles, and areas of expertise. 
  • Flexible, with support for multiple training methods and modalities, including virtual instructor led training (VILT) and self-paced training
  • Data-driven, with reporting and analytics functionality that allows you to track both learner behavior and learner performance. 
  • Hands-on, so that you can create interactive simulations through which your salespeople can develop and practice practical skills. 
  • Easy to integrate with existing sales enablement tools and technologies such as your learning management system (LMS) and your customer relationship management (CRM) solution. 

Don’t Focus Solely on Technical Proficiency

Technical skills, digital fluency, and product knowledge are only part of the equation in enterprise software sales. Your training should also focus on teaching the right soft skills to your salespeople, as well. By the time onboarding is complete, each salesperson should: 

  • Understand how to build trust and cultivate a lasting relationship with a prospect. 
  • Be able to keep track of deadlines, conversations, appointments, and follow-ups.
  • Possess excellent written and verbal communication skills. 
  • Know how to engage in active listening. 
  • Develop effective time management skills.
  • Have the capacity to quickly pivot their strategy.
  • Tailor their communication to whoever they’re talking to. 

Basically, your software sales training program needs to teach people how to communicate, empathize, adapt, and negotiate. It may even be worth your time to spin your sales training out into a secondary sales-oriented leadership training course

Deliver Personalized Content

The value of personalization doesn’t just apply to your customers. It’s also immensely useful for more or less any corporate training initiative, sales training included. By tailoring the learning experience to each individual salesperson, you can improve both engagement and retention, thereby helping your sales team be more knowledgeable, capable, ultimately, successful. 

Our suggestion? Look into adaptive learning. That’ll allow you to incorporate artificial intelligence (AI) into your sales training and provide trainees with dynamic learning paths, real-time feedback, and personalized performance assessments. As an added bonus, you’ll be able to scale your sales training much more easily as your business grows — no more worrying about whether you’ve got the necessary training resources in place. 

Understand the Customer

One of the most common sales mistakes we see involves focusing too much on the product and not enough on the person. You can talk about your software’s feature-set and provide evidence of its value until you’re blue in the face — it’s not going to accomplish much if you aren’t tailoring that messaging to each prospect’s unique situation. That’s part of the reason why it’s so important for salespeople to develop soft skills.

Don’t just stop at skill development, though. Your training should also demonstrate how salespeople can apply those skills during a deal negotiation. For any given prospect, a salesperson should know how to answer the following questions: 

  • What are the underlying needs and problems behind this prospect’s use case? 
  • What specific product features solve those problems and fulfill those needs? 
  • How can I best convey the value of those features to the prospect?
  • What objections am I likely to encounter during the sales process? 
  • What’s the most effective way to overcome those objections?  

Obviously there’s no one-size-fits-all answer to those questions. They’re something your salespeople will address on a case-by-case basis. The key lies in teaching them what to look for and what to ask a prospect to find the answers they need. 

Monitor, Iterate, and Improve

Plenty of businesses take a “one and done” approach to their training. They think that once a new salesperson’s been onboarded, that’s it. As a result, they miss out on a ton of potential opportunities — not just for professional development in their salespeople, but also to improve, streamline, and optimize their training. 

Don’t make the same mistake. Monitor your training for any potential weaknesses or bottlenecks, and create a strategy that encourages regular upskilling and retraining. That’s why it’s so important to choose a training solution with analytics and reporting capabilities. 

You can’t improve anything if you’re flying blind. 

Learn How to Build a Winning Sales Training Program

Now that we’ve reviewed a few best practices for software sales training, let’s talk more about what’s actually involved in developing your program. 

You can start with our Q&A on what should be included in a technical sales training program. From there, have a look at Technical Sales Training: 6 Do’s and Don’ts.  Finally, we recommend exploring how training fits into sales enablement with How Do You Develop a Sales Enablement Strategy?