Best Sales Trainers

According to a recent report from Hubspot, more than 90% of companies invest in some form of sales training. Because of the amount they are spending — up to $7,000 per employee — these companies want to make sure they are getting the best sales training possible. They spend a lot of time researching their various options so they can choose the one that’s the right fit. They narrow it down to those that are respected in the industry and are considered leaders in their field. They also make sure that their sales training methods get high marks from their colleagues.

However, many companies overlook the most obvious differentiator: Do they have the best sales trainers?

Having the right trainer makes all the difference. It means that your employees taking a course are more alert, more engaged, and — most importantly — more likely to retain what they learn. They can take the skills that they have developed and apply them immediately. And they can pass along these skills to others on their team. That’s why online sales training is an important step in building a team that meets and even exceeds your goals. Here are some of the qualities that you should look for in a trainer:

 Years of sales experience. The best trainers are those who have already spent years honing their own skills. They are seasoned sales professionals who can provide their students with real-life examples and discuss different strategies for approaching the types of challenges all sales teams face. They have negotiated deals, coached colleagues, and built successful teams. Check out the qualifications of the trainers at any company you are considering. If they don’t have actual sales experience, that should be a red flag.

 Knowledge about today’s industry. The way that we approach sales is constantly changing. Sales methodologies that were considered cutting edge a decade ago are now outmoded. A different set of skills is required to really master the recurring revenue model that most companies are turning to today. If the trainer you are considering is too focused on closing the deal, and not focused enough on maintaining long-term relationships with customers, they probably aren’t well-versed in recurring revenue. That’s a big strike against them. Sales teams — especially those at SaaS companies — need to understand what today’s customers are looking for and how they best sell to them.

 A focus on learning. It’s a great thing to have a passion for teaching, but the best trainers also make sure that their students completely understand the concepts that they are explaining. This means that the old-fashioned lecture format is out. It’s just not the way that students learn today. Recent research revealed that after 30 days, students retained less than 10% of what they learned during a lecture. Instead, trainers should use a more interactive style. There should be plenty of time for questions, as well as for sharing the challenges that they are encountering.

 At Winning by Design, the leader in accelerating and optimizing recurring revenue for B2B organizations, our trainers are the best in the business. They have won numerous awards and are frequently asked to speak about their experiences teaching the latest sales techniques. They lead sales training courses for beginners that will bring the newest members of your team up to speed, as well as the best sales coaching programs designed to improve the skills of your most skilled account executives.

Solution Architect Krista Zink said the training provided by Winning by Design helped her team stand out in the crowd. “I have taken a lot of sales training classes in my career, and one of the best was the one I just finished with Winning by Design,” she said. “They gave us a unified sales methodology to help us increase sales while setting ourselves apart from the competition.”

Sales Speakers and Trainers

If you conduct an online search for the best sales trainers of all time, you just might come across Winning by Design’s Founder and Co-CEO, Jacco van der Kooij. One of our customers described him as a “force of nature,” and that sums him up pretty well. He’s passionate about teaching teams about the power of the recurring revenue model and is generous in the way he shares the knowledge he has learned over the years. He also happens to be one of the best sales leadership speakers today, and is often asked to be the keynote speaker at major conferences.

 But when it comes to outstanding sales speakers and trainers, you can’t go wrong at Winning by Design. Our team of trainers and revenue architects is constantly speaking on podcasts and on panel discussions about how we help companies achieve sustainable growth across their entire revenue team. And they aren’t afraid to challenge conventional wisdom if it’s wrong. John Grispon, Lead Revenue Architect at Winning by Design, had this to say recently on the Pavilion Podcast: “I often hear sales leaders say: ‘I want people that are great closers.’ And I just think, ‘That is baloney.’ You don’t want great closers, you want great openers, people that are great at discovery. That’s where you win the sale.”

 There’s a reason why our trainers make such compelling direct sales speakers: They hone their skills in the classroom day in and day out. They are the reason why we are winning awards for our work. When Training Industry, the leading research and information resource for corporate learning leaders, released its list of the Top 20 Training Companies in 2022, high on the list was Winning by Design. Having the best sales speakers also helped us to rack up more than 500 five-star reviews on G2, where we are ranked among the best in numerous categories, including Sales Training and Customer Success Training. 

But we’re most proud of what our students have to say about our trainers. Gabriella Bispo, Account Growth Manager at Pipefy, said it was our trainers that made the difference for her. “The vast knowledge of the trainers, the high quality of the materials, and the techniques used to teach us were incredible,” she said. “I am more confident and more productive.”

Famous Sales Coaches

Where do you find the best sales training programs for your team? When it comes to training people in a variety of roles, Winning by Design has the right mix of interactive training sessions, engaging instructors, best-in-class frameworks, and detailed blueprints for each step along the customer journey. We offer the best-in-class open courses that are perfect for one or two of your team members or even a small group to hone their skills. Our private classes have curriculums that can be tailored to your company’s needs, and our coaching sessions reinforce the strategies that your team has learned along the way. 

And as we mentioned, the top sales trainers in the world are at Winning by Design. Amanda Hill, Sales Enablement Partner at Tipalti, said she has nothing but praise for the team at Winning by Design. “The caliber of the trainers is immense,” she said. “Each one that I have worked with has impressed me with their knowledge and their ability to keep things relevant and exciting.”

 Looking for the best startup coach to help your early-stage company begin to scale? Or maybe your growth-stage company needs help bringing down its customer acquisition cost? Winning by Design’s revenue architects can implement a common language that your entire team — marketing, sales, and customer success — can understand. We can also provide you with a universal methodology that ensures you have a well-orchestrated customer experience. It’s all codified into your own playbooks, processes, and systems. That’s something that not even the most famous sales trainers or most famous sales coaches can provide.

Best Sales Books

According to Close, one of the best sales books available today is Jacco van der Kooij’s “Blueprints for a SaaS Sales Organization.” The book, according to the editors, “distills decades of combined experience building high-performance SaaS teams into detailed instructions that help sales managers design, implement, and execute better sales plans.” That’s pretty high praise.

 There’s a reason why “Blueprints for a SaaS Sales Organization” made this list of the top sales books of all time (and why it’s found its way onto many other similar lists): It literally wrote the book about how SaaS sales teams are built. There were no existing sales frameworks purpose-built for a recurring revenue framework, so the Winning by Design created one. This book is the bible for SaaS companies. It’s also one of the best sales books for beginners in recurring revenue companies. Here’s a little of what it advises: “Time is the only resource you can’t replace, and in today’s fast-moving market your competitors are quick to leap ahead of you and cash in on the market you and your marketing dollars created.” 

Because the recurring revenue framework is still fairly new, the courses offered through Winning by Design are constantly being updated to include the latest information about SaaS sales. Our innovative new courses focus on augmenting management skills, prioritizing customer success, and mastering the recurring revenue model. They are all available through Winning by Design’s highly regarded Revenue Academy.

There are a lot of books competing for the title of best sales book of 2022. But “Blueprints for a SaaS Sales Organization” deserves a place on the shelf of anyone interested in how recurring revenue companies are evolving.

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