Jen Allen

Chief Evangelist at Challenger

18 Insights · 6 Questions · 9min Read · 12min Listen · Connect with Jen on LinkedIn

Lack of leads? Lack of buyer alignment? Teach where prospects go to learn. When you are teaching in those spaces, don't teach the solution. Once you've won over someone on that message (they look at the problem the same way you do) make sure you don't fall short at the goal line by just assuming that they'll be able to socialize the problem inside of their business in the way that you would.

Here’s what Carl Ferreira said about Jen:

Jen Allen. You got to talk to Jen. She's fantastic. She's Chief Evangelist Officer over at Challenger. Huge fan of Challenger. The content that she puts out on LinkedIn is very different. A lot of content on LinkedIn, especially in like the sales ecosystem, is very entry-level. It's for SDRs, it’s a lot of prospecting tips and things like that. So Jen is a breath of fresh air because it's content designed for the close, for the deal, for a more experienced closing type of rep, and I learned a ton from it. I consume a lot of her content. —Carl Ferreira, Director of Sales at Refine Labs → Listen

What are 3 ways that your team converts your market into revenue?

1) Teach where prospects go to learn. What I mean by that is: instead of just relying on the traditional sales process to hopefully find someone who's ready to buy, figure out where your customers go to learn, with or without you, and make sure you've got a message there.

2) When you are teaching in those spaces, don't teach the solution. Teach your interpretation of why the problem exists and alternatives to solving that problem. So make it problem-teaching, not solutions-teaching.

3) Once you've won over someone on that message (they look at the problem the same way you do) make sure you don't fall short at the goal line by just assuming that they'll be able to socialize the problem inside of their business in the way that you would. So rather, spend time making sure you've armed them to go tell the problem story in the way that candidly you would tell it if you were in the room.

What are 3 hard problems that you recently overcame?

1) Lack of leads. This is very timely, it’s how I got this new job. I sold in the large enterprise space and I was a hunter rep (or someone who just focused on new logo acquisition). Last year, I was just seeing a dramatic drop in the amount of leads that were coming in the door. And so rather than just go back and beat marketing over the head with it and try to figure out what can marketing can do, that's how I started getting more involved in things like social and podcasting and that sort of thing to try to generate interest, again to my earlier point, where people go to learn. Have a presence there.

2) The lack of buyer alignment that exists today. I think probably everybody feels this because now we're all, in many cases, operating virtually, we just don't have the benefit of customers who see each other in the hallway and can talk about the problems together. And so just having a really disconnected buying group that are coming on for Zoom, and then jumping into their next room, was a problem. It was just really difficult candidly to sell what I sell last year. So, part of what I did to overcome it was think differently about the agenda and the time that I was spending that with them. So, instead of trying to cram a ton into one call, because that was my one and only opportunity with the buying group, slowing that down and saying, “my first call them has to be on aligning on the problem. I shouldn't even get to solution in that call. If we align on the problem, then we can talk about solution. Then when we've aligned on the solution, then we can talk about pricing.” I think previously I was trying to just cram all of that into one meeting.

3) “What else could I do to keep this job interesting?” This actually relates to number one. I'm someone who's always considered themselves to be a lifelong seller, and that was perfectly fine for me, but I started getting an itch last year and say, “I know I don't want to go to the manager track. I know I don't want to go down the enablement or a leader track. What else could I do to keep this job interesting?” And that's when I looked to turn what I was kind of doing on the side of my desk, in terms of the social stuff, into more of a formal role of evangelism.

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What are 3 roadblocks that you are working on now?

1) Dispersed teams and figuring how to get customers to make decisions in a really effective but efficient manner, is still a work-in-progress. Like the second one above. That's something I candidly think will be on my to-do list for every single year moving forward. So, I would say that's still something I've made progress on, but still have more work to do.

2) A different competitor for the same category of spend. Specific for our business, one of the things that I've observed as a result of everybody having to go digital, is now we have a different type of competitor. We play, traditionally, in the sales training / sales enablement space. But now, with many companies saying, “gosh, with virtual, we need to invest in sales tech, and we need to become much more sophisticated there.” It's not that they are a competitor in the sense of what we do, but they are a competitor for the same category of spend. So to summarize it, thinking differently about how do I frame against new and emerging competitors that may not be our traditional set.

3) Socializing for the business. It relates to my new job. Because so few people have an Evangelist role, formally, I don't think it's really understood or understood how to use effectively. So, one of the things that I'm working on right now is socializing for the business. How does Customer Success think about where Evangelists can step in? How do AEs? How does marketing? Sort of playing nice in the sandbox with all those functions.

What are 3 mental models that you use to do your best work?

These all come straight from the bible of the Challenger sale, so I am absolutely a convert on that:

1) Make the “Pain of Same” greater than the “Pain of Change.” In every sales conversation I have, I am thinking about “how do I make it so that customers first see that the pain of what they're currently doing is much greater than the cost of whatever solution I'm asking them to implement?” And it goes a little bit beyond just the cost of the solution, more so around the idea that I can buy a better solution from you or somebody else. But I also, in the back of my mind as a customer, know that that road to better is going to be like my political capital at risk. It's going to be budget. It could be my team looking at me being like, “Why did you change this process? What we were doing was good enough.” And so the mental model that I'm approaching every sales conversation with is: avoid the urge of building up the benefit of the upside of if they go with us, and really, really hammer home the cost of whatever they're currently doing. So I refer to that as, “Make Pain of Same greater than Pain of Change,” which one of our clients actually came up with years ago. That's number one.

2) That mental model, but applied to Opportunity Prioritization. So I think a big mistake I made early in my career, and candidly up until a couple of years ago, was when I would get a territory in January, I’d looked through and I'd say, “what are all the sexiest names, biggest companies, biggest sales teams?” I'd spent a lot of time going after them, not appreciating that in many cases, their Pain of Same was not greater than their Pain of Change. They may have already had an established methodology. They may have built something. I would kill a lot of time and productivity trying to convince them to do something different when I had a ton of companies who maybe had no sales methodology at all. Or, maybe a ton of companies that were shifting the portfolio of what they sold from hardware to software. So, taking that pain of same mentality and applying it to opportunity prioritization would be number two.

3) Cost of Inaction (COI). Sort of the same theme, but when we get to the point at which we are talking about solutions, another big mistake that I made previously, that I think have done a better job at (still work-in-progress) is: it's so easy for us to jump to ROI because every customer asks about it. At the end of the day though, that does very, very little for a company who perceives that the cost of changing is significant. And so one of the mental models that I learned from Challenger was this idea of Cost of Inaction. When customers want to run to ROI, they are trying to defend the value of the investment, but oftentimes the conversation that we need to have first is, “what happens if you do nothing?” We refer to that as Cost of Inaction or COI. So being really disciplined in making sure when I get to Proposal, or when I get to Solution, I'm not just putting up an ROI number, but I'm also giving a comparison point for what happens if you decide to do nothing differently about this problem.

What are 3 techniques that GTM teams need to try?

1) Evangelism. So I'm biased, but if you have any sort of disruptive element to your business, and you don't have customers who are naturally going to gravitate to the new and differentiated solution that you offer, evangelism is such a powerful way to take some of the pressure off of marketing, and, candidly, sellers, to go out there and socialize the problems that you solve. Socialize the pain of same. Socialize the cost of inaction. I think it's a really cool thing, even if it's a side of the desk job, like it was for me last year, to have someone dedicated in your business doing that. So that's number one, evangelism.

2) Challenger. Again, biased, but I think, personally, just because of my own experience with it: in a market where risk aversion, where cost, where all of these things are increased, and make it increasingly difficult for customers to buy, I could candidly understand 5-6 years ago, when the market was thriving, why people would opt not to do Challenger. But in an environment like this, when no-decision, status quo, these are some of our biggest competitors. I think right now, Challenger should at least be considered by anybody who is selling something that's disruptive. So again, biased. I have to say what I believe.

3) What I described above around Opportunity Prioritization. Moving away from just the standard employee size, or sexiness of the logo, to try to pick which opportunities we spend our time on and actually thinking about it through the lens of, “what do we have to teach that customer and is that enough to actually make meaningful progress against their business problems?” So those would be my three.

Who are 3 operators that should be our next guests and why?

1) Josh Braun. My number one dude. Josh Braun is one of the more influential people in my own career. If you don't follow him already, Josh writes content that is beyond helpful. It's stuff when I first read it, I started thinking like, “why is he not charging for it?” He does in his classes, but he also puts a lot of content out for free. So I view him as someone that's a real helper. I've, candidly, learned a lot about cold calling, cold emailing, cold outreach from him.

2) Darren McKee. So he used to be at BetterUp. He just moved over to an organization called Wellthy. Darren is someone that I think is a great example of someone who is very active on social, but productively. He's not active saying like, “this is why our solution is the best.” He starts really smart conversations that relate back to what he sells. I think he embodies a lot of the characteristics I think sellers should be thinking about today.

3) Leslie Venetz. For those of you that don't know her, she was one of the earlier salespeople to get on TikTok. And I know TikTok, in many ways, is perceived as not relevant for B2B. But, she's a amassed a really big following. Some of the themes that Leslie touches on are things like women in sales, and diversity in sales, and how you show up and be your authentic self in sales, and just conversations that I think, as a result of COVID, as a result of like a deeper awareness of mental health, many times we, as sellers, are not comfortable having inside of our organizations. So I think she presents a really compelling view of things to be mindful of things, to be thinking about, as you navigate the sales role.

Work with Jen → Challenger is hiring!

Listen to Jen → Winning the Challenger Sale Podcast

February 2022 · Interview by Chris Morgan, Host of Market-to-Revenue

Market-to-Revenue Podcast ⚡️ Lightning-fast interviews with GTM operators in sales, success, product, and marketing.

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