How Jen Allen Sells: Sell The Size of Their Problem, Not Your Solution

Welcome to 2023. A new year, especially for Jen Allen. 

For the previous 18, she’s worked at the same organization. Well, effectively the same organization – first CEB, then Gartner when it bought CEB, and then Challenger, which Gartner sold off as a private entity in 2018.

So, three different companies, but all the same goal – selling sales consulting. Since 2012, that sales consulting has revolved around Challenger – the revolutionary sales model based on the book of its same name, written by lauded sales researchers Matt Dixon and Brent Adamson. 

In 2022, Allen wasn’t just selling sales consulting for Challenger. She also became the organization’s first Chief Evangelist, hosting the Winning the Challenger Sale podcast. 

Except – no longer. After years of helping sales teams transform at Challenger, just a few weeks ago, she decided to leave the company.

Why?

“This last year was interesting because I created this Chief Evangelist role at Challenger, and I think it opened my eyes,” Jen said. “I was interviewing people every week on the podcast from different walks of life, and it opened my eyes to the fact that I always attached my value to Challenger, right? Like, am I only good because I am selling an amazing product? But it opened my eyes to the fact that there is more to my story than just Challenger – it made me feel empowered.”

So now Jen has started anew in 2023, which includes co-launching her own social media community, Social Social. As far as what comes next beyond that, well, that part of the story is still being written. 

But we’re quite certain it’ll be something worth writing about.

In her 18 years at CEB and Gartner and then Challenger, Allen became well-versed in the Challenger Sales Model. And she also got a first-hand look at how hundreds of sales organizations sell, how hundreds of sales organizations manage and react to change, and how hundreds of sales organizations ultimately succeed (or fail).

Based on all of that, what has she learned? What has she adopted? And what does she believe will work best moving forward in what could be a difficult 2023? 

We sat down with her for our latest edition of How I Sell to find out:

1. What motivates you to come to work each day?

It’s a passion for the problem that we solve.

I don't think you stay with an organization for 18 years if you're not immensely driven by the problem that you solve. And so, for me, once I understood what we were solving for, it became this infectious thing where I just wanted to have as many conversations with as many C-level executives as I could to help them look at the world in a different way.

2. What’s your sales philosophy, in three sentences or less?

I don't need three sentences – it's sell the problem, not the solution.

One of the things we spent a lot of time learning about in Challenger was that we studied customer buying behavior in B2B. One of the biggest changes we saw over the past 12 years is that buying groups keep getting bigger. And it doesn’t matter what the product is – even seemingly smaller products are getting 12 people involved.

That’s because it’s not the size of the product that is so disruptive but that it’s replacing a manual process. And the mistake that I made a lot early in my career and then learned to fix, thankfully, was that I was going in and trying to convince people why our solution was so amazing.

But what I failed to appreciate is that when you get 11 people – which is the average-sized buying committee today – in a room, and you're trying to convince them of a solution, the problem is that most of them don't even agree that this is the most important priority to solve. And so, when I took a step back, I realized my job as a seller is not to sell the solution. But to go in and help a buying group agree that this is a problem they need to solve.

That was a big change for me. I spent a lot less time focused on demoing my solution and a lot more time highlighting the problem and how it was affecting everyone in the room.

3. How do you make your prospecting stand out?

For me, I've always sold to C-level. If I'm going to ask a C-level executive to give me their most precious commodity, which is time, I am going to be damn sure that I've earned that privilege.

And that’s something I take really seriously.

So, before I reach out, I Google their name, I see if they are on a podcast, I see what they are posting on LinkedIn, and I’m looking for a few things. One is how does the CEO talk about what the company is trying to do? How do they talk about what makes that hard? How do they talk about how they're trying to get there?

And then, when I'm doing my outreach, I'll get to the point quickly. I'm not going out and saying, “I'm Jen, I'm from Challenger, and we're the world's leading training organization,” because nobody cares. Instead, I’ll use what I found and lead with that.

The reason is what I'm trying to show in my prospecting is that I am not here to talk about myself and what I sell. I'm all about what you're trying to achieve and how you're trying to achieve it. And I want to show you that I'm not just putting you on some list and blasting everybody with the same information. Instead, I'm intentionally curious about your business.

What I find is that when I do that, yes, it takes a little longer to write those emails, but my response rate is so high that it's a no-brainer. And I want that to be my reputation rather than just blasting someone with our G2 rankings.

4. What’s your favorite discovery question?

It’s a two-parter:

• How important is this problem to solve?
• How important is this problem to solve right now?

One of the big mistakes I made a lot in my discovery conversations early in my career is I would get so excited because we'd have a really good sales call. But I never really understood how this problem related to other priorities.

So, especially when it’s a group buy, I ask that first question, and usually, I get head nods, right? But when you ask the second question, that's where I think people start to reveal their honest position. It's like, “Well, maybe this can wait six months.”

When I started doing that, what I found is I was able to qualify and disqualify more effectively. Because sometimes, it feels like people are really interested, but they're having even more interesting conversations around something else.

5. Do you have a preferred closing technique?

The two biggest competitors we face today are reluctance to change from the status quo and indecision. So, if you think about those two being the two biggest competitors, there's an approach I use a lot.

I’ll meet with the person who I think is going to buy. They’ll often say something like, “We're going to wait; we're going to punt this.” In response, I'll say, “Look, you are in a really tough position. I know that you want to do this. If you do this, though, you have all this risk and cost and time that goes into it. But respectfully, I wouldn't be doing my job if I made this conversation easy, right? Like, I can't just say sure, let's punt it until 2024. I know you want me to, but I can't. So, hear me out.”

And then I'll go to the rational cost of inaction, which is what happens to this problem if you continue not solving it. This is not ROI; it’s the cost of inaction.

For me, we were always selling better sales conversations. So, I'll say something like, “OK, how many sales conversations a month are your sellers going to have? You are going to have 15,000 more of these conversations a month, and yet we both agreed you are not getting the results that you want out of them. And all that time, the problem doesn't go away, right?”

That’s confronting them with the rational side of it.

Then the second part of it is the emotional side, which is that you started this conversation by telling me that every time you go into your boss's office, you have to come up with another excuse for why you're missing the forecast. Do you really want to sign up for 12 more of those conversations before we meet again?

Then I’ll go for the close with something like, “So all I'm asking is, would you be willing to have an honest conversation about where we can de-risk this? Maybe we start with a pilot. Maybe we start with something smaller so that you don't feel as uneasy about moving forward? And then, after you let me help you work on that narrative for your boss, if you still feel like it's not the right time, I'll leave you alone. I'll call you back in six months.”

For me, that’s a lot better than just rolling over and saying, “Sure, I'll call you next year.” That’s not being aggressive, it’s just holding each other accountable.

6. Is there a habit you have outside work that helps you sell better?

I think the most important thing in selling right now is creativity. Because it's just so freaking hard to cut through the clutter and get people’s attention. And I think it's so easy to fall into these really stiff and professional ways of doing outreach.

And so, one of the things that unlocks creativity for me is music.

I grew up as a total music geek. And so, when I'm feeling really stuck, or I have writer's block or whatever, the number-one thing that I do is I will go out, I'll take a walk, and I'll listen to music. And what I find is it just activates something in me. So, for me, it's music.

And the other thing is going to concerts. I went to Coldplay in May and everyone's like, “Shut up about Coldplay” (laughs). But it was the coolest concert because I was like, “this is magic.” And I think when we can connect that kind of emotion to what we do, sales becomes an amazing career.

7. How do you use LinkedIn when selling?

LinkedIn totally changed my career.

As I talked about, I created the role of Chief Evangelist for Challenger. The thing that sparked me to do it was Challenger had put out this study that showed buying groups spend 83% of their time away from the sales rep. And it also said 27% of that time was spent independently doing research online.

And I was like, my gosh, we're sitting here trying to sell to these people. But they're not wanting to engage with the sales rep yet because they're still learning. So, I said, let me go to the channel where I feel like most of my prospects are spending their time. And so, I started creating content on LinkedIn around the challenges we were seeing and helping solve.

All of a sudden, all of these C-Level titles started showing up in my DMs. Soon, we were sourcing deals from it – 7-figure-deals coming from LinkedIn posts, because the problems I was speaking about were problems affecting these people. There’s no way I could’ve done that without LinkedIn.

8. What has been your biggest failure in sales, and how did that experience transform you?

This is an easy one. Because I never wanted to be in sales, it never felt natural to me in the beginning. And so I always felt like I had to mirror myself after someone else. I would look at whoever was the top performer and say, “How do I show up more like them?”

A couple of years into my career, I was very fortunate to pitch to a customer – a female head of marketing at a really big company. Per usual, I was giving her all my buzzwords and saying all the things I thought I was supposed to say. And she stopped me, and she asked me, “What does Jen think about this issue?” 

I just froze because I was so used to saying the things that I thought I had to say. 

That was a really pivotal moment. Because when I sat there and thought about it, and then I shared my perspective, she said, “That's what I'm interested in.”

And so it taught me that trying to be someone that sounds professional or sounds smart or sounds like a sales expert is one of the worst moves I ever made. It’s when I realized that my own voice, my own story, my own interpretation, was a superpower.

That unlocked all the opportunities in the world for me. I wish I had learned it sooner. It's the number-one thing I tell early-career sellers – don't shy away from who you really are. Because that is truly the only thing that we cannot commoditize, our own story.

Follow our How I Sell newsletter for bi-weekly interviews with some of the most innovative sellers going today.