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Imagine this: One of your star reps has spent months communicating with a prospective customer. You’ve helped your rep counter every objection. Your rep has worked with half a dozen stakeholders and muscled through a sales cycle spanning nearly half a year. Then, just when you believe you’re at the finish line… a previously unmentioned stakeholder swoops in and dashes the whole deal, leaving you and your team empty-handed and out many months of hard work. 

Enterprise sales can be a challenging, high-risk, high-investment field. While avoiding situations like the one above is impossible, you can increase your chances of success by pursuing enterprise sales training for yourself and your team. 

Let’s dive into the nitty gritty of enterprise sales training. I’ll cover some of my top tools and trainers to help level up your team’s skills in enterprise sales. Then I’ll give you some of my best tips and hacks for helping your team crush their targets. 

Key Elements of Enterprise Sales Training

You need to understand a few things about enterprise sales before we get started. First, what is enterprise sales—and what makes it different from other types of sales? Enterprise sales involve high-investment purchases. When working in this type of sales environment, you can expect longer sales cycles and more stakeholders.

The good news about enterprise sales is that, generally, purchases are made as a part of a strategic initiative. As a result, the sale is more visible inside the client’s company, both to you and your sales team.

Your team will need specialized training to succeed with all these key differences between enterprise sales and other sales environments. Some of the elements you should look for in an enterprise sales training program include:

  • Enterprise buyer behavior vs. consumer buyer behavior
  • The intersection between sales and marketing
  • Opportunity management
  • Building consensus among multiple stakeholders
  • The basics of trading value
  • Objection handling for enterprise sales

Let’s take a closer look at all things to do with enterprise sales training. I’ll start by walking you through the best tools and trainers you can use for your training efforts, then move into my top tips for conducting enterprise sales training that gets real results for your team. 

Best Tools for Enterprise Sales Training 

Strong, effective training tools are essential for delivering and reinforcing the best sales training lessons to your team. You’ll need an inside sales training tool capable of delivering incredible results for enterprise sales teams to reach your goals.

What features should you consider when looking for a sales training tool or resource for your enterprise sales team? First, your tool should be deliverable and sustainable at scale. Even if you don’t have a large sales team, you want to ensure that information and reinforcement are consistent across your organization.

Related Read: The 14 Tools You Need to Nurture Your Dream Clients

You’ll also want to explore an enterprise sales training solution that contains various learning modules for different focuses and experience levels. If you choose a tool or resource with too narrow a focus, either some of your team won’t receive the training they need, or you’ll need to invest in multiple tools to train your entire team.

Finally, ensure your tool or resource includes a mindset shift. If you neglect to train mindset in your sales staff, you won’t see a true behavior change. Instead, start by training your staff to adopt a one-up mindset and instill a culture of continuous learning in your team. 

Let’s look at three choices for tools or resources with all of these features and more. 

Sales Insights Lab 

Sales Insights Lab offers individual and team-based training. Their courses follow a five-step process, teaching reps to demonstrate insight, disqualify weak leads, solve problems, offer clear next steps, and develop a prospecting blueprint. 

Founder, Marc Wayshak, has many years of experience in various areas of sales. He has also published books like Game Plan Selling and The High-Velocity Sales Organization

Pricing for Sales Insights Lab’s training programs is available upon request only. 

Many customers have found success from this program, with one learner saying:

"We've had a 271% increase in sales. I knew we could do better. I wasn't sure how to get there. [Sales Insights Lab’s] program turned out to be the missing link." 

ASLAN Sales Training 

ASLAN offers various inside sales training programs and courses across industries and roles. They offer training tailored to inside sales, field sales, call center sales, and sales managers. Some of the courses offered include:

  • Account management
  • Business development
  • Prospecting
  • Inbound and outbound selling

The company name, ASLAN, comes from the character in The Chronicles of Narnia. Essentially, it serves as a reminder to be other-oriented and customer-focused in your approach to sales and all things in life. 

ASLAN’s pricing is also available by quote only. They have many happy clients, including some Fortune 500 companies. One customer says:

“Within a year of implementing ASLAN’s complete account development process, we grew revenue 5% while customer demand was declining. And we saw incremental revenue growth of 46% within existing accounts.”

Sales Accelerator 

My Sales Accelerator has one mission: to give your sales reps the exact language they need to open the conversation, create opportunities, and advance each sale. Individual reps can use the Accelerator independently, or managers can put their entire team through my program. 

The Accelerator offers various courses across the spectrum of sales skills, tactics, and strategies. The program's self-paced and highly customizable nature allows each enterprise sales rep to get the training they need to become their most successful self. 

I’m the founder of The Sales Blog. I’m also the author of four sales books and an experienced trainer and coach. I’ve helped over three hundred teams implement the Revenue Growth Blueprint through this program. 

My pricing is transparent. I offer a year of unlimited access to the Accelerator and its associated materials for $997.

According to one VP of Sales who used the Accelerator for his team, 

“I highly recommend this sales training platform. Bringing Sales Accelerator into my sales organization has allowed me to level-up several reps, improve sales engagement, and improve our conversion ratios." 

Top Enterprise Sales Trainers and Speakers 

Another way to support your enterprise sales training efforts is to bring in a sales speaker. If you’ve never booked a speaker, you may wonder if booking a sales speaker is truly beneficial for your team. 

Sales speakers offer several benefits to your enterprise sales team. You can bring in a sales speaker to:

  • Motivate your team
  • Kick off a new initiative
  • Provide external insights
  • Kick off a new training program
  • Introduce new skills or methodologies

Let’s take a look at three speakers you may want to book for your next enterprise sales training initiative. 

Jeff Winters 

Jeff Winters is the founder and CEO of Sapper Consulting. Winters' business aims to help sales reps spend less time cold calling and more time closing. Sapper Consulting offers B2B lead generation services and sales consulting assistance.

Winters’ years of experience in the B2B sales space make him a strong candidate for a sales speaker for enterprise sales teams. 

Some of Winters’ past speaking topics have included shortening the B2B sales cycle, booking more meetings, and more. 

Listen to Jeff Winters speak here: 

Marcus Sheridan 

Many people in the world of sales and marketing are familiar with Marcus Sheridan. The author of They Ask, You Answer, Sheridan offers keynote speeches, workshops, trainings, and more. Sheridan’s goal is to get your brand or team out of the rut they’re stuck in and back on track to hitting their targets.

Sheridan is an energetic and dynamic speaker who is sure to engage your team and provide them with unique and actionable insights. 

Marcus Sheridan regularly speaks on many topics, including the subject matter of his bestselling book, building customer trust, and more. 

See Sheridan in action here: 

Anthony Iannarino 

I am an experienced sales professional, trainer, and speaker. I’ve delivered keynotes and workshops in eight different countries. The secret to my programs’ success? Pre-work and post-work. Including these elements ensures that my words stick with your reps, helping you get the most from your session.

During pre-work, you’ll have the opportunity to customize the keynote to your audience. Then, my post-work helps ensure you have all the tools you need to implement the changes discussed in our time together. 

I’ve spoken on a wide range of topics, including:

  • Coaching the Sales Force
  • Dealing with Obstacles and Difficult Conversations
  • Value Creation: How to Create and Sustain Relationships of Value

I strive to educate, entertain, and provide actionable strategies for the modern sales approach enterprise sales teams need today. Check out one of my keynotes below.

5 Tips for Enterprise Sales Training 

Using any of the tools or speakers listed above will help set your team up for success in enterprise sales training. However, to really knock your targets out of the park, you’ll need some actionable tips and tricks. How can you make your training as effective as possible?

The single competency most salespeople miss when training enterprise salespeople is the business acumen that would make the salesperson credible, an expert, and an authority. After this, most training doesn't even touch on creating value for the client within the sales conversation.

Keeping that in mind, let’s go over five tips you can use to get the most out of your enterprise sales training efforts.

1. Prioritize Prospecting Training 

Prospecting and pre-call process training are the first pieces of the puzzle for any successful sales training program. 

Your training program needs to help your reps learn how to identify prospects and their pain points and challenges. As I mentioned briefly above, your team needs to understand how to approach prospects with a value-first mindset if they want to succeed in enterprise sales. 

Relationship nurturing and organized prospecting following a sales prospecting plan are also vital skills you need to focus your training efforts around. Choose a training program that helps your reps focus on time-blocking for prospecting activities like research and cold calling. 

Lastly, the best sales training program should help your team build the tools, strategies, and processes they need to succeed in enterprise sales.

2. Offer Sales Leadership Training 

Training isn’t just for your new team members—it’s for everyone. You should include sales leaders in your training programs. Sales leaders require specific training in leadership, accountability, communication, and more. 

Offer sales leadership training to your current managers and explore offering these courses to emerging leaders on your team to build a talent pipeline for your organization's future. 

Related Read: How To Find t he Best Sales Leadership Development Program For Your Business

Besides offering training specific to your managers, you should also ensure you include your managers in the training offered to your reps. Your managers will be responsible for coaching and reinforcing training for your reps after the training sessions are complete. Without this accountability, your training efforts will be wasted, and you will likely see no behavioral changes.

3. Teach Reps to Focus on Value (Not Features) 

When selling something as high-risk and high-value as most enterprise sales offerings, you and your reps may be tempted to focus on features and functionality. However, this is a mistake. Ensure that your training programs teach reps the importance of focusing on value.

The focus on value shouldn’t just be at the bottom of your sales funnel, either. You should be trading value in every interaction with your prospects. What value can you provide on the first call? Why should they agree to book a meeting with your team? Your training program should help your sales reps answer these questions and more. 

You’ll also want to explore a training program that allows your team to practice in the field. This is how you start to get the behavioral changes your team needs.

4. Avoid Teaching Legacy Sales Technique

The problem with a majority of sales training programs for enterprise sales teams and others is that they train legacy sales tactics and techniques that don’t work in the modern sales environment. 

When you train your team with legacy tactics, you’re training them to be better at a failing system. Instead, you want to use modern sales techniques that will give them confidence and the language they need to advance enterprise sales.

One of the most important pieces of the modern sales puzzle is having a one-up mindset. When your sales reps are “one-up,” they have the knowledge and confidence to provide real value to prospects and customers. In other words, they’ll have an easier time advancing and ultimately closing sales and creating happier customers. 

5. Make Training Collaborative 

Without a mindset shift, no amount of sales training is going to stick. Instead of dictating sales training programs to your reps, collaborate with them to ensure they’re building skills they need and skills they’re interested in improving. 

Finding a sales training program you can tailor to your team, your industry, and your needs is vital. In enterprise sales, you’ll want to trade the idea of sales training for a sales development plan. It takes time and effort to develop enterprise-level skills and competencies. As a result, you’ll need more than a few hours of training to foster these skills in your reps.

You’ll also want to put processes in place to hold reps accountable for enacting the new processes and practices they’ve learned in training. Without that accountability, new ideas and methodologies won’t stick, and your training time will have been wasted. 

Get The Most From Your Enterprise Sales Training 

Effective enterprise sales training is essential if you and your team want to close more deals and hit your targets. Remember that the business environment and sales processes are always changing, so if your team isn’t engaged in regular training, they are not simply not getting better—they are becoming less effective over time.

Using the five tips outlined above will help you ensure that you can leverage your chosen enterprise sales training tools and mechanisms to their maximum potential. 

Every team has different needs from its training platforms and tools. If your team would benefit from a highly targeted and customizable online training program with modules covering everything from cold calling fundamentals to advanced sales leadership tactics, explore my Sales Accelerator today.

Post by Anthony Iannarino on April 8, 2023

Written and edited by human brains and human hands.

Anthony Iannarino

Anthony Iannarino is an American writer. He has published daily at thesalesblog.com for more than 14 years, amassing over 5,300 articles and making this platform a destination for salespeople and sales leaders. Anthony is also the author of four best-selling books documenting modern sales methodologies and a fifth book for sales leaders seeking revenue growth. His latest book for an even wider audience is titled, The Negativity Fast: Proven Techniques to Increase Positivity, Reduce Fear, and Boost Success.

Anthony speaks to sales organizations worldwide, delivering cutting-edge sales strategies and tactics that work in this ever-evolving B2B landscape. He also provides workshops and seminars. You can reach Anthony at thesalesblog.com or email Beth@b2bsalescoach.com.

Connect with Anthony on LinkedIn, X or Youtube. You can email Anthony at iannarino@gmail.com

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