Insight Selling

Objective: Transform into an insight seller. // Price: $129/month
30-day, 100% money-back guarantee
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Learn to sell the way winners do.

Today's top sellers don't just sell the value of their products and services, they become the value. They educate buyers with ideas and perspectives—an advanced sales technique known as “insight selling.”

In our breakthrough research report, What Sales Winners Do Differently, we found that insight selling is the biggest difference between those who win and those who come in second place—and now we’re going to teach you how to do it.

Based on our popular book Insight Selling, this self-paced online learning program will help you reach your full potential and not only meet, but exceed your sales goals.

By the end of the program, you’ll know how to shape buyer agendas, avoid common insight selling mistakes, and tell convincing stories that differentiate you. Enroll today to transform into an insight seller.

Click to watch a preview of one of the lessons >>


What Will I Learn?

Insight Selling is our advanced consultative selling program. We’ll walk you through how to become an insight seller and position yourself as invaluable to the buyer’s success. You’ll learn:

  • How to land insight discussions with top decision makers
  • How to differentiate yourself and stand out from the pack
  • 10 questions to challenge buyer thinking
  • How to identify buyers who buy insights (and those who don't)
  • How to tell convincing stories that demand buyer action
  • How to make the business impact of your solution clear so you can sell more with less buyer resistance
  • Step-by-step how to lead effective insight selling discussions
Want to dig deeper into the content before taking the leap? Get the full details on each program lesson below.
Lesson 1
Lesson 2
Lesson 3
Lesson 4
Lesson 5
Lesson 6
Lesson 7
Lesson 8
Lesson 9
Lesson 10
Lesson 11
Lesson 12
Lesson 13
Lesson 14
Lesson 15
Lesson 1:
What Is Insight Selling?

Today's sales winners don't just sell the value of their products and services, they become the value. They educate buyers with new ideas and perspectives during the sales process. They are insight sellers.

In this lesson you'll learn:

  • What insight selling is and the role of seller as change agent
  • The top 10 selling attributes that most separate winners from second-place finishers
  • The 3 areas where winners do well, and second-place finishers fall short
Lesson 2:
The Two Types of Insight Selling

For years, the core advice given to sellers has been to diagnose needs, craft the most helpful solution, and then communicate that solution in a compelling way. On its own, this doesn't win sales like it used to. In this lesson, you'll learn:

  • The 2 primary ways you can apply insight selling in your interactions with buyers
  • How to use the concept of cognitive reframing to drive change with ideas that matter
  • The 3 characteristics of insights that matter
Lesson 3:
Buyers Who Buy Insights (And Buyers Who Don’t)

Not every buyer buys new ideas or appreciates insight in the same way. In this lesson we explain how to identify the buyers who will be most receptive to insight selling, and how to avoid those who aren’t worth your time. You’ll learn about:

  • The 6 buyer personas that exist in sales, and how they prefer to buy. Based on these personas, you’ll learn to adjust your sales process in order to maximize your results with each buyer type
  • Which buyer types are most responsive to insight selling
  • Why some prospects aren’t good buyers for innovative ideas and insights
  • How to identify different buyer personas and develop the right sales strategy for each
Lesson 4:
Building Rapport

People trust people they like. People buy from people they like. People want people they like to succeed. Your ability to make connections with buyers and build rapport is a key to your sales success. This lesson covers:

  • 10 essential tips for building real rapport with prospects
  • The building blocks for building rapport and making connections
Lesson 5:
Understanding Trust in Insight Selling

If you want to have success with insight selling (or any selling for that matter), there’s one ingredient you can’t do without: trust. Without it, even the best sales tactics will fall flat. In this lesson you’ll learn:

  • How trust and insight selling work together
  • The 4 components of trust, and how they work together
  • How insights and trust work together to create long-term sales success
Lesson 6:
Uncovering the Full Set of Needs and Desires

All sellers need to be able to uncover buyer needs. Uncover problems and pain (afflictions) and desires and goals (aspirations) and you create the foundation for sales success. In this lesson you'll learn:

  • Questioning techniques to uncover the full set of prospects needs while at the same time position your solution as the most helpful
  • 3 types of questions to use in your next sales conversation
  • The best approach to uncover the root cause of needs
Lesson 7:
Understanding 3 Key Components of Value

All good sales starts with knowledge of your buyers. How do you help your buyers? What value do you deliver? How can you communicate this value to buyers in a memorable and enticing way? In this lesson you’ll learn:

  • The 3 components of value, and what happens if a component is missing
  • How to position value early in the sale, when inspiring buyers to consider something new, and late in the sale, when trying to win business
  • How to position your value favorably against the competition
Lesson 8:
Maximizing the Impact of Your Solution

What type of success will your buyer achieve if they buy from you? What failures will they see if they do nothing? The ability to clearly communicate the impact you can have on your buyer is an essential component of insight selling. This lesson will teach you:

  • The two types of impact in sales
  • How to make that impact tangible to buyers
  • Why demonstrating impact builds credibility
  • How articulating impact maximizes the buyer’s urgency to buy from you
  • How to build your own impact model
Lesson 9:
Bringing the New Reality to Life

The ability to paint a picture of positive change for your buyers can be the difference between success and failure in sales. In this lesson you’ll learn:

  • How to present a compelling image of how your prospect's situation will improve if and when they buy from you
  • The 3 steps you must take to effectively convey a new reality to buyers
  • How combining quantitative and qualitative reasoning will maximize the impact of your presentations
  • Why conveying a new reality can inspire collaboration and commitment from buyers, leading to new sales and healthy client relationships
Lesson 10:
Telling a Convincing Story

The sellers who excel at insight selling tell Convincing Stories that demand buyer attention and action. In this lesson, you’ll learn:

  • The 3 questions every Convincing Story must answer for the buyer
  • The 7 key elements that make up a Convincing Story—leave even one out, and your story will lack the impact necessary to inspire action from your buyer
  • How dissatisfaction layering is essential to making your message compelling
  • How Convincing Stories can make a buyer personally invested in working with you, greatly improving your chances of winning sales
Lesson 11:
Leading an Opportunity Insight Discussion

When you’re trying to sell a new idea or insight proactively to a buyer, we call it “opportunity insight.” This lesson gives you the tools you need to successfully put opportunity insight selling to work, drive demand, and fill your pipeline with new opportunities. You’ll learn:

  • How asking questions at the wrong time, in the wrong way, can derail your meeting and sale
  • 7 steps that will lead you to the best outcomes when you’re selling insight and ideas proactively
  • The balance you must strike between advocacy and inquiry if you want to make the sale
Lesson 12:
Questions that Generate Insight

Many think that insight selling is only about educating buyers through presentations and telling them what to do. They’re missing out on the full impact they can bring to the table. This lesson will teach you why asking the right questions can lead to improved sales success. Specifically, you’ll learn:

  • How asking incisive questions changes the way your buyer sees things and opens their minds to new opportunities
  • How questions can draw people out of their comfort zone—and why this is a great thing for your sales
  • 10 questions that will spark insight, inspiration, and action from your buyers
Lesson 13:
Balancing Advocacy and Inquiry

Sellers are often told they need to “just ask great questions.” Others are told they to be able to pitch, persuade, tell stories, and present. In reality, balancing advocacy (telling, sharing, presenting) and inquiry (asking questions) is the most powerful approach. This lesson covers:

  • The keys to success for balancing advocacy and inquiry
  • Why you fall into the talk too much trap
Lesson 14:
10 Keys to Becoming a Source of Insight

Becoming a trusted source of insight isn’t something that you can just snap your fingers and become. This lesson lays out the 10 things you must do to get there. You’ll learn:

  • Why being viewed as an “industry insider” in 2 different ways is critical to your success
  • Why you must combine idealism and realism if you want your insight to have true impact
  • How not having a distinct point of view can derail your insight sales efforts
  • Why being comfortable with discomfort is important to your sales success
Lesson 15:
Creating Insight Conversations

The act of creating new conversations that lead to sales—also known as prospecting—is perhaps the most overanalyzed of all the stages in the sales process. It’s also one of the most misunderstood. In this lesson you’ll learn:

  • A simple framework to create conversations and bring insights and ideas to senior executives
  • The 4 initial contact methods that lead to insight discussions
  • How to use trigger events to set insight-focused meetings

“I am at over 180% for my quota for the month of Feb. Which is traditionally a slow month. The program works if you are willing to invest the time. BIG THANKS TO THE RAIN GROUP!”

- Victoria Mazzotta, Managed Sales Rep, Modern Postcard

“This program has armed me with a comprehensive approach to building relationships with clients and closing more deals. I'd highly recommend immersing yourself in the resources and watching your closing ratio rise. Thanks for everything!”

- Mike Pool, Mid Market Acquisitions Rep., Rackspace

“Having the best value proposition for our clients is essential to their success and our success. So we go to great lengths to get it right for our clients when developing new offerings, or entering emerging markets. We came up with the best value proposition possible using the ‘Convincing Story’ framework in this program. This has proven to be very useful in engaging with clients globally in a way that allows Aurecon to connect, convince and collaborate with them to secure new engagements.”

- Colin Dominish, Client Relationship Director, Aurecon

What Does Membership Include?

15 Training Lessons

Content is available in video and text to consume at home or on-the-go, at your own pace.

Downloadable Tools & Checklists

Learning happens by doing. Our practical tools help you apply insight selling right away.

Knowledge Check Quizzes

Put your learning to the test with our interactive quizzes to test your retention of key points in each lesson.

Case Studies & Role Plays

Visualize the program techniques in action with real-world examples of insight selling success in every module.

Convincing Story Tool

You’ll get a handy tool to help you develop a powerful convincing story and deliver it to buyers.

Access to Research

Get access to exclusive content from the RAIN Group Center for Sales Research, including What Sales Winners Do Differently.


Who should take this course?

Sellers and professionals looking to go beyond basic sales skills and learn advanced consultative selling techniques, providing real value to buyers over and above the products and services they sell.

How long does it take to complete the course? Are all lessons available at once?

All program content is available and accessible on-demand as soon as you sign up.

There are 15 lessons, each lasting approximately 20 minutes. When completed at our recommended pace of 1 lesson per week, you’ll finish the program within just 4 months.

If after completing the lessons you would like continued access to the program content and tools, you are welcome to stay subscribed as long as you’d like.

Is the content downloadable?

Lessons are available to view in text and video for your convenience and learning preference. The program tools and resources are also yours to download and keep to reference whenever you like.

What’s the cost?

Typical sales training programs cost thousands of dollars, require travel, and often teach you tactics that simply don’t work in the world of sales today.

Tuition for Insight Selling is $129/month. You’ll be making an important investment in your career to achieve breakthroughs in your sales success. You’ll make this investment back many times over in just your first sale.

Please note that the program is a monthly recurring subscription. Once enrolled, your credit card will be billed automatically every 30 days until you notify us to cancel.

How does the 30-day, money-back guarantee work?

We think you’re going to find the program content compelling and the tools invaluable. If you don’t agree, notify us within your first 30 days of membership and we will be happy to refund your payment, no questions asked.

I want my team to take this course. Do you have group rates?

We offer discounted rates for groups of 5 or more. If you have a team that would benefit from Insight Selling or are interested in bringing the program on-site, contact us for more information at or call 508-405-0438.

Enroll Now for $129/Month

If you want to learn to educate buyers with new ideas and perspectives, collaborate with buyers throughout the selling process, shape buyer agendas, and differentiate yourself from the competition, Insight Selling will help you get there. Click below to enroll now. 

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