NEW WEBINAR:
Building a successful commercial insight engine
Nearly 90% of buyers claim not to involve a supplier when they identify problems. Reacting only to problems the buyer has already uncovered leaves sellers dependent on established demand that is outside their control.
What if sellers not only reacted with solutions for established demand, but also helped identify new problems that created new demand? How might that change your success rates? How might that unlock your growth potential?
Download to watch the second installment of our Leading The Challenger Sale webinar series, where Andee Harris, CEO at Challenger, and Jon Perera, CMO at Highspot, will present “Building a successful commercial insight engine.” Learn how creating new demand requires marketing and sales working together to disrupt conventional thinking at the outset of the buying journey.
Complete the form below to watch this webinar on demand
Complete the form below to watch this webinar on demand
Discover more webinars
NEW WEBINAR:
Building a successful commercial insight engine
February 27, 2023
Presented with Highspot, this session is all about how you need sales and marketing working together to build a successful commercial insight engine.
On-Demand Webinar:
Winning new business in a sideways economy
February 9, 2023
Presented with West Monroe Partners, the session is all about winning new business in a sideways economy—how to sell when no one wants to buy from…
WTCS S3 | E11 2022 Year in Review
December 27, 2022
In this Episode 11, 2022 Year in Review, our new host, Andee Harris, CEO of Challenger recaps all of the top themes that disrupted the status quo of…
WTCS S3 | E10 Preparing for Negotiations
December 27, 2022
In this Episode 10, Preparing for Negotiations, Jen Allen welcomes SVP of Sales at Challenger, Adam Maude to discuss the ways in which sellers can…
Winning the Challenger Sale: Season 3 Replay
October 28, 2022
Catch up on all of the episodes of Season 3, Winning the Challenger sale webinar series.
WTCS S3 | E9 Creating a Mutual Close Plan
October 14, 2022
In this Episode 9, Creating a Mutual Close Plan, our host and Chief Evangelist Jen Allen welcomes Dan Flood and Alex Schrager, two of Challenger's…
On-Demand Webinar:
Winning new business in a sideways economy
Something we’ve learned as the only sales methodology that emerged during a recession: Great sellers are born out of a downturn economy.
Those sellers know that “we’ve always done it this way” won’t work when hesitation is high, and buyers are reluctant to buy. Our experience has shown that change is even more critical in the face of a recession. So how do you know what change is needed and where to focus?
This Challenger webinar from the Leading The Challenger Sale series, presented in partnership with West Monroe Partners, is all about winning new business in a sideways economy—how to sell when no one wants to buy from you.
Complete the form below to watch this webinar on demand
Discover more webinars
NEW WEBINAR:
Building a successful commercial insight engine
February 27, 2023
Presented with Highspot, this session is all about how you need sales and marketing working together to build a successful commercial insight engine.
On-Demand Webinar:
Winning new business in a sideways economy
February 9, 2023
Presented with West Monroe Partners, the session is all about winning new business in a sideways economy—how to sell when no one wants to buy from…
WTCS S3 | E11 2022 Year in Review
December 27, 2022
In this Episode 11, 2022 Year in Review, our new host, Andee Harris, CEO of Challenger recaps all of the top themes that disrupted the status quo of…
WTCS S3 | E10 Preparing for Negotiations
December 27, 2022
In this Episode 10, Preparing for Negotiations, Jen Allen welcomes SVP of Sales at Challenger, Adam Maude to discuss the ways in which sellers can…
Winning the Challenger Sale: Season 3 Replay
October 28, 2022
Catch up on all of the episodes of Season 3, Winning the Challenger sale webinar series.
WTCS S3 | E9 Creating a Mutual Close Plan
October 14, 2022
In this Episode 9, Creating a Mutual Close Plan, our host and Chief Evangelist Jen Allen welcomes Dan Flood and Alex Schrager, two of Challenger's…
Winning the Challenger Sale, Episode 3: Email Pitfalls To Avoid
Our popular Winning the Challenger Sale Series is now entering its third season. This monthly live webinar invites sales professionals and commercial leaders to join us Thursdays at 11 AM ET as we open up the Challenger™ playbook.
More than just a webinar series, sellers, managers, coaches, and sales leaders get practical advice and actionable insight for the day-to-day execution of the sales skills and behaviors proven to win in complex selling and buying environments. Our third episode aired live April 14 and covered “Email Pitfalls To Avoid.”
To kick things off in their latest webinar, our hosts, Mike Randazzo and Jen Allen took a poll, asking whether email is dead. 94% of the audience said, “No,” and Jen agreed, saying, “Email isn’t dead, but bad emails are.”
This begs the question: How many of our hearts stop momentarily when we hit SEND on an initial sales email and suddenly think, “Oops, should I have done that?” Because, as they say (and “they” is everybody by the way), “You only get one chance to make a first impression.”
Appropriately, “Email Pitfalls To Avoid” is what Mike and Jen are best at, and what a great (and universal) topic it is, because the truth is that most of our emails get stuck in the “mental spam filter” of our intended customer.
What does that mean, you ask?
Well, as Lavender—a digital marketing agency focused on connection-driven sales strategies—says, “Because potential buyers have adapted to an endless stream of inbound requests, the average read time for them to categorize the email (reply, forward, delete) is 13.4 seconds.”
So, fine, people have short attention spans, but what’s the impact to a seller? It means that you have a limited amount of time to engage your potential buyer, so make it count!
The problem is, as Mike and Jen put it, we either spend too much or too little time crafting our emails, and for various reasons. But rather than over or underthinking, your emails need to be:
- Relevant
- Thought-provoking
- Built to teach
The webinar goes on to discuss Challenger Emails, where Mike and Jen analyze sample emails and their core components:
- Subject line
- Credibility
- Reframe/Curiosity
- Powerful Request
And the three big pitfalls to avoid:
- Mistaking “Personalization” with “Relevance.”
- Telling them they have a problem vs. asking them thought-provoking questions.
- Overlooking the importance of your CTA/request.
Number 3 in this list is interesting because Mike and Jen point out something that can be more important than CTAs, and that’s the CTL (“Call to Learn”), because without the CTL, the CTA can be foggy at best.
The two hosts finish up the webinar by explaining the difference between “Getting the call scheduled” and “Getting the prospect in the right frame of mind prior to the call.” They also discuss the Do’s and Don’ts of “Challenger Email Pitfalls to Avoid,” General Rules, and, as always, Key Takeaways.
So next time you hit SEND on an initial sales email, you can now breathe a sigh of relief (which is actually doctor-recommended).
***
By the way, you can also review Challenger Emails 101 by checking out our archived Season 1, Episode 2 episode called: “Capture Attention by Leading With Insight.”
Our next webinar, which is on the second Thursday of every month, is “Opportunity Prioritization,” airing live on May 12, 2022. Register for this episode and the full series here. If you missed this webinar on “Email Pitfalls to Avoid,” you can watch it here.
Want more ideas on how to win? Catch the latest Winning the Challenger Sale podcast here.
Winning the Challenger Sale, Episode 2: Social Selling: Your Secret Weapon in 2022: A Wrap Up
Our popular Winning the Challenger Sales Series is now entering its third season. This monthly live webinar invites sales professionals and commercial leaders to join us Thursdays at 11 AM ET as we open up the Challenger™ playbook.
More than just a webinar series, sellers, managers, coaches, and sales leaders can get practical advice and actionable insight for the day-to-day execution of the skills and behaviors proven to win in complex selling and buying environments.
Our second episode with Mike Randazzo and Jen Allen aired live on March 10 and covered “Social Selling: Your Secret Weapon in 2022.”
So, what is Social Selling? Social Selling is a marketing strategy that allows your organization to target business prospects on social media and develop a network of potential leads from those posts.
Throughout the Social Selling webinar, Jen and Mike shared tactical advice on how Challenger brings the Challenger choreography to life in social, tips and tricks for your social presence and content, as well as pitfalls you can avoid and best practices you can start doing right away to bring a credible source of insight to your customers.
To kick off the webinar, Mike and Jen shared an interesting stat: You only have 5-6% of your customer’s attention, and even if you have it, you’re probably asking the wrong question. Double bad news, right? Surprisingly - no. The reason customers are out there is to learn— to seek out opinions or facts—not buy.
“Today’s buyer journey is rarely linear,” say Mike and Jen, “and buyers are learning without us. Rather than move left to right along a purchase process, customers seek validation and input from a variety of sources—both internal and external.” To corroborate this, Challenger’s analysis of buyers shows that 83% of the buying group’s time is spent without the seller (i.e. meeting with the buying group, researching independently online or offline).
While many sellers respond to this trend by turning up the noise (i.e. more emails, more cold calls), a small segment of sellers understand that customers are actively seeking to learn about the problem they’re looking to solve in social channels – which means you should sell your prospective customers on the value of your company or the value of your solution.
Sellers need to change the goal. Instead of selling when your customers are trying to learn, teach when your customers are trying to learn.
By using social content, you build mindshare with potential buyers to increase the likelihood that your company will be top of mind when a non-buyer becomes a potential customer of your products or services.
So, what are some social tips to get started today?
- Update your profile.
- Set a weekly connections goal.
- Comment/engage with other posts.
- Set a calendar invite to write at least 1 post a week.
- Build your reframe.
Concerning that last tip, “Build your reframe”, near the 15-minute mark of the webinar, Mike and Jen talk about leading with customer problems and insights—that your simple social posts need to be Surprising, Sizable, and Solvable (the 3 S’s). And around the 22-minute mark, the hosts share a social content cheat sheet, which is headlined by 4 pillars: Posting, Sharing, Commenting, and Connecting.
In a nutshell, as Jen and Mike point out: “Sellers should support the learning journey in social media by teaching not selling, sharing content that is helpful, and attracting customers to learn not buy.”
The Challenger way of thinking is to lead with insight, a way of thinking. The customer’s main question is asking whether you’re going to help them on their journey . . . and that answer should always be a resounding “yes.”
***
Our next webinar, which is on the second Thursday of every month, is “Email Pitfalls to Avoid,” which will air live on April 14. Register for this episode and the full series here.
If you missed this webinar on Social Selling, you can watch it here.
Want more ideas on how to win? Catch the latest Winning the Challenger Sale podcast here.
Commercial Teaching: More Than Just An Early-Stage Strategy
In our most recent Winning the Challenger Sales Webinar, we went deep on "Discovery" calls and shared some tips for how to leverage "high-gain" questions. A high-gain question is an open-ended question that does two things:
(1) Unlocks information prospects typically don’t share with salespeople (i.e., the true goal of “discovery”) and
(2) teaches the prospect about a blind spot in their business (i.e., similar to the Socratic method). They’re not easy; they take planning and practice to do well.
I’ll go deeper on discovery calls in a later blog, but I first want to outline a critical consideration “discovery”.
For Challengers, a successful discovery call looks like this:
- They demonstrate credibility by revealing research conducted in advance
- They share a strong hypothesis around the customer pain point they plan to expose
- They ask high gain questions that turn into "teaching opportunities" and provide the prospect an engaging or "aha" moment where they reconsider status quo
The discovery call represents the first and most obvious "teaching opportunity” in what will hopefully progress into a qualified opportunity and ultimately a “closed-won” deal.
But the important point to consider is that the job of a “commercial teacher” and the process of discovery is just beginning in the initial discovery call. In fact, there are many discovery and teaching opportunities that arise throughout a sales process/buying journey.
If you’re making the most of “teaching opportunities” throughout the funnel, you continually discover more about your prospects’ motivations, and find strong footholds to reframe their perspective. This is evident in their reactions.

Commercial teaching is not simply a choreography for first sales calls and early-stage conversations, although it works very well in those situations. It’s a tool for teaching and discovery used throughout the sales process/buying journey. We’ll be exploring this idea in early June.
Join us on June 3rd as we dive deep into the next sales moment that matters on the next episode of Winning the Challenger Sale: The "Teaching Opportunity" .
Access the replays of Season 2 Winning the Challenger Sale episodes.