Sales Hustle is now Sales Transformation
Sept. 22, 2021

#156 S2 Episode 25 - From Running Events To Loving A Hunter Role at Challenger with Jen Allen

On this episode of the Sales Transformation Podcast with Collin Mitchell he's joined by Jen Allen, Key Account Executive at Challenger, and Advisory Council Member in 1440 Sports.

Jen talks about her transition from running events to being a top apex hunter over at Challenger. Not only that, she shares some tidbits about why the Challenger mindset is key for you as a salesperson and breaking down the stereotypical salesperson.

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00:52 Jen discusses her life going on towards sales and her current status in life

04:10 The lessons learned and debunking the usual stereotypes of a "salesperson"

10:26 Solving business problems for Jen is something that everyone should get into especially if you're in sales

18:03 An interesting concept about people being overly concerned but is actually the complete opposite

23:09 Final thoughts from Jen and how to connect with her


05:19 "Having a good sales leader can really make a big difference on whether you love the career or don't love the career."

09:38 "I don't know what you think about sales but to me walking in a room that are completely skeptical of you, of why they're there, what you're even there for, who you are, what you represent, makes me want to get up in the morning and do this job. And I love going in changing someone's opinion about the way they look at their business."

"Like someone else did the hard work to sell it. Now you just have to make sure you don't drop the ball. I wanted to be the person that convinced that company that you don't think you need."

16:38 "That grit, that tenacity to be like 'I'm gonna go out and challenge people and get them to think differently,' is something we've always viewed as you either have it or you don't. I think the unfortunate thing is that we as organizations just don't tend to teach our people to behave that way. "

17:40 "If I'm truly there as a seller to help my customer, I have to ask those hard questions because otherwise I'm just letting them sit in unnecessary cost and risk, and that's not being a good partner to our customers."

Learn more about Jen in the link below: 

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[00:00:00] In the world of sales, you either sink or swim or breakthrough to the next level. My name's Colin Mitchell, and this is sales transformation, a new kind of sales show designed to bring you through the epic life-changing moments of elite sellers. So you can experience your own sales transformation.

[00:00:24] All right. Welcome back to another episode of sales transformation as always. I've got a fantastic guest for you today. I'm going to be speaking with Jen Allen. Key account executive over at challenger. A challenger is the company behind the bestselling book, the challenger sale. So we're going to dig into her experience, how she got into sales, how she got involved with challenger and everything in between Jen, welcome to sales transformation.

[00:00:50] How are you? Thank you so much. I'm great. Happy to be here. Yeah, I'm excited to, uh, have you on, we met not too long [00:00:59] ago and planned this and then something unexpected happened and here we are making it.

[00:01:06] Yeah. So I'm curious, let's just start at the beginning. How did you get into sales and then let's take it from there. You bet. So I never considered myself ever, ever, ever having a career in sales, which I'm sure like half the people that come on here say I could have never guessed. Funny story. I actually went to school for recreation and park management, which is like basically gym class throughout all college.

[00:01:33] Um, and the reason I did that is because I thought I wanted to get into event management. And I did that for a while. I managed like bowl games and final four travel. And I love like the scenario planning aspect of it hated the standing in the bus parking lot, waiting for all the people who got to go to the game to actually come back.

[00:01:51] Um, So that wasn't as fun as I sort of thought in my head. Um, and then I actually had a college roommate who was working at the company. It was [00:01:58] called corporate executive board or CEB at the time. And she said, you should come here. It's really fun. Lots of cool people, like really smart stuff. And so I just ended up into a really entry level, kind of like an SDR role for existing accounts and, um, started my career in it back in oh four.

[00:02:14] Very cool. All right. So yeah, I'm waiting for the day that somebody comes on and it was like, I wanted to be in sales when I grew up for Halloween, I dressed up as a salesman or whatever. Um, I'm hoping one day that will be the case. I did have one person on that took sales. Courses in college. That was a first, um, I don't know how good they were, but, but that was the first, uh, so yeah.

[00:02:43] You know, sales is always somebody say a plan B. Exactly. Yeah. Yeah. For me it was a little different. Listeners have heard me tell this story way too many times. So I'll keep it short. [00:02:57] Uh, for me it was, I didn't go to college. I barely made it through high school and, uh, there was no opportunities for me. So sales was it, there was nothing, there were no other options.

[00:03:06] So I guess it was sort of my plan a, but I didn't really know. I was like moving furniture. That was my job. And I enjoyed it cause I was outside and I got to stay in shape. But, uh, yeah, sales was like a, definitely an upgrade from moving furniture for me, for sure. The first time when you first started selling, what were you selling after market printing supplies and hardware and all kinds of stuff.

[00:03:30] And it was lots of like phone calls, tons of phone calls. Uh, the training was very formal and intense. It was like here's the script and a list of names and there's the.

[00:03:43] Yeah, it was that bad. Um, and it was like, yeah, just, you know, say what other people are saying around here that are doing well. I'm like, okay, sure. Until I was, yeah. And then I started saying something that was working and I was getting deals [00:03:56] and then somebody else was like, you shouldn't say that. And I'm like, why it's working?

[00:04:00] And he's like, because it's not true.

[00:04:06] Yes. Yeah. Sometimes you gotta be careful mirroring what you hear on the sales floor. Uh, yeah. All right. So, uh, event planning, didn't wasn't as, uh, as you thought, got into sales. And what was your experience there in this, uh, like SDR role? What did you learn? Yeah. I think like a lot of people who end up staying in sales for a long time, my first manager was an incredible manager.

[00:04:32] And, um, one of the things that really stood out to me was that she wasn't what I had viewed a classic sales person to be. She wasn't like the slick, like, let me make you a deal kind of thing. And she was super, super smart, super sharp. And. I was really comfortable going head to head at the time we were, um, sort of selling a, an annual research subscription to heads of [00:04:55] marketing, and she would talk to like the head of marketing at Coca-Cola and just go so hard at why they were doing what they are doing.

[00:05:01] And I remember sitting back in my chair, being. How does she get there? How did she start and get to a point where she was so comfortable having that kind of a conversation with someone that, that was like that senior, because in my mind, at the time that person was like a celebrity and I thought like, how do you do that?

[00:05:16] And so I was just like, totally mystified with her and thought, I want to be like her. I want to figure out how she did it. I want to get there. And that's sort of what, like got me really, really pulled in to sales is seeing someone who did it so well, so flawlessly. And who took the time? I think really to coach me on what she was.

[00:05:33] Wow. That's, that's incredible. Um, you know, having a good sales leader can, can really make a big difference on whether you. Love the career or don't love the career. Yes. That's an understatement. And I've had my fair share of people that I think looking back may not [00:05:54] have been in the right job. Uh, nothing, no knock against them, but just it's, it's a hard job, right?

[00:05:58] It's one of the reasons I've been a lifer sales rep is because I can sit back and realize like being a sales manager is not easy. Like no. You're in the middle between a bunch of people complaining upwards and a bunch of people complaining downwards. And I have all the respect in the world for people who choose to take that job on.

[00:06:16] It's just not one that I've ever wanted. Yeah. And it's good to be clear on that because so many people think like if they get in sales as an individual contributor, like I need to become a sales leader or that's that's the career path and it doesn't have to be, and, you know, sales, leadership. Definitely not for everyone.

[00:06:40] I was definitely managing a team. Well, before I should have been made a lot of mistakes that I had to learn from, which is horrible, because you're learning at the expense of your team. [00:06:53] I love the way you put that. It's so true. Right. And it's like, I think you're absolutely right. Especially like, if you are the type a go getter that people typically associate with sales, it's like, I have to get that next promotion.

[00:07:04] I'm actually super encouraged by the amount of people. Yeah. I see on LinkedIn now that are, have careers similar to mine where they've been selling for over 15 years. And it's not like you're lazy or you're not a go getter. You just appreciate that selling and managing are two very, very different skills.

[00:07:20] Right? Right. Yeah. And, and, and it's, it's such a wrong assumption to think that great sellers. Are just ultimately going to be great leaders. Yeah. Sometimes they're actually the worst. I love that. You said that let's do it like, oh yeah. Yeah. Because you know, the way I did it works for me. It should work for you right.[00:07:52] 

[00:07:52] Wrong. So how, how long did you stay there and in that role and, and, and walk me through kind of what, what happened next and in your experience? Yeah, so like most things in life, um, I was fortunate because my manager who I loved so much decided to move to. And when she moved, um, our managing director at six at the time said, look, you're just too new to take on her job.

[00:08:17] However, we don't have a backfill. So you're more than welcome to do the job until we find someone that we want to hire that can do it. Full-time and I was always raised by my dad to be working harder than anyone ever asks you to write. Like, if you have an opportunity to do the next job, don't wait until you get.

[00:08:34] Paid for it. And I know that goes against a lot of folks mindsets and that's okay. Everybody's different. But to me, it was like, this is my opportunity to prove myself. And so I took on her book of business and because I think I had that drive inside of me of, I need to prove. That I can do this to [00:08:51] myself, let alone to these other people.

[00:08:53] I was, I ended up really being successful in it. And six months later, unpaid, um, the managing director finally came to me and said, look, I think you actually have what it takes to be in this job. We'd love you to do it. Full-time. And so from there I spent a lot of time, um, just doing the individual contributor account manager role, renewing the book of business.

[00:09:11] Over time. I then added folks under management under me. And, um, it was more kind of like a player coach role. So I was never a complete manager. I always had my own territory. And then I realized like account management and sales are so different, right? Like, I don't know where you spent, you know, it sounds like you spent more of your time in sales for initially.

[00:09:30] It's just, it's like two different beasts and it always was, it was in the back of my mind. Like, could I be good at sales? Like right now I'm talking to people who've already decided to pay us. What if I talk to people. Weren't even sure if we were worth their time. And so that curiosity drew me to say, like, I want to try it.

[00:09:46] So I think it was after seven years of doing account [00:09:50] management, I put myself into a hunter role at the firm and I loved it. Like, I don't know about what you think about sales, but to me, walking into a room with people that are completely skeptical of you, of why they're there, what you've already been there for who you are, what you referenced.

[00:10:06] Makes me like, want to get up in the morning and do this job. And I loved going in and changing someone's opinion about the way that they looked at their business. Like that was something I thought never got stale. It never got boring. There's always a new company to learn. There's always a new business problem to learn.

[00:10:22] And I just became so infatuated with that component of this. And so it sounds like you had a little bit of with the account management stuff, kind of going into that rule and then realizing that you weren't as fascinated with that, or you didn't enjoy that work as much as that one. Yeah. Like, I liked the idea of solving business problems for my current clients, but I felt kind of like, you've been [00:10:49] handed this, right?

[00:10:49] Like someone else did the hard work to sell it. Now you just have to make sure you don't drop the ball. I wanted to be the person that convinced that company that you don't think you need. But you do and be really good at really understanding their business and why they needed it and not be like what I had in my mind of like a classic sales rep.

[00:11:08] Like I really wanted to be different. And I will say, you know, as a woman and I was young at the time, um, not anymore, but at the time, like I also felt an element of like, it was a very male dominated. And I wanted to go into a room and really get someone who was like, maybe waving me off to say, like, I need to take her seriously.

[00:11:28] And I will say like, that's, that's come so far. Like, I don't feel that today in my job, but at the time, like, you know, whatever it was 15 years ago, I really felt that I think that was a driver. Yeah. Yeah. So, and it sounds like, you know, I'm to, I'm going to guess your personality type is you like a challenge[00:11:48] 

[00:11:50] clearly?

[00:11:57] Uh, I'm the same way, like things get too easy or like, I don't know, not to say account management is easy, but there's less, you know, it's kind of a lot of the same work in a lot of cases, um, where, you know, convincing somebody that well, not convincing. Yeah. Maybe convincing them they have a problem and that you can solve that problem for them is a bit more of a challenge.

[00:12:20] And, you know, you gotta do what lights you up. Not everybody's for sales, not everybody's for sales leaders. You know, and, and really knowing yourself and having awareness of like what, you know, drives you, I think is really important in choosing, you know, what sales career path you, you should have. I completely agree.

[00:12:40] And I think like, even today, if I reflect on what it was like selling 10 years ago, Like the [00:12:47] things that I was doing 10 years ago would never fly today. Right? Like I really had the belief that like, if I was just accessible enough and likable enough and I worked hard enough, people would buy. And I honestly think that, like, that was enough.

[00:13:02] It was, and the way I ended up at challenger challenger was actually part of CEB. Gartner bought it. They spun us off, but the way I ended up in challenger is because I was first exposed to it. I realized like I was falling into that classic, like relationship builder profile. And as a result, like when things were fine with the customer, The, I would have great relationships and I would have great business, but then like, oh, 8 0 9 hit.

[00:13:28] And I'm like, where'd all the customers go. Where'd all my friends go. Right. They're gone. And it really changed my perspective around what I needed to be doing as a seller and how to actually create a relationship, not just on like my like ability, but actually on like the back of a business conversation.

[00:13:42] Right. And so that's how I ultimately ended up in the challenger group because I was [00:13:46] exposed to it. This totally changed my perspective. I want to go sell this to other people who are just like me trying to figure things out. Wow. Okay. So tell me through that experience in Alliance in oh nine, like, did you know, did your, did your bottom line get affected pretty, pretty bad where you said, wow, I need to kind of think about this a little bit differently.

[00:14:08] A hundred percent. Like I remember when it hits. I had, I think I had New York territory at the time. And, um, so it was a lot of banks Fs and that industry obviously was massively disruptive and I had really good relationships and banking and financial services are also relationship sellers for the most part.

[00:14:26] Right. And so it was like a mutual thing, but when their businesses are falling apart, when they're watching the industry consolidate, when they're watching all this go down around them, I liked Jen, it's nothing against Jen. I just have so many bigger things that I need to fix right now that I have to let Jen down.

[00:14:42] And I realized it was because I wasn't actually [00:14:45] doing anything to help them with those big things that they were needing to fix. I was just like, Hey, you need a report. I'll pull it for you. You need me to come here and do a presentation. I'll do it for you. Right. And I was just like super responsive and reactive.

[00:14:56] And that was a big, big lesson for me. Is. That's fine when things are good, maybe, but there's always going to come a point there's last year was COVID then it was the economy and that's just not going to be good enough, but like, I don't know. What's your experience with that? I mean, were you, I'm assuming you were selling oh, 8 0 9 when things kind of, I actually perform better under crappy circumstances.

[00:15:20] Like I perform well when my back's against the wall and I have to, um, or things are not great. Like, you know, when times are tough and, and, you know, I don't know everybody's situation, but, you know, even just with the pandemic, there's a lot of particular industries that got crushed and there's, you know, people that were much more reluctant to.

[00:15:42] Make any big purchases and [00:15:44] sales cycles got stretched out. And, and there's some real things that that happen, but there's also a lot of people that just have a lot of excuses as well. Um, and it's, it's when T in times like that you can be more creative. You can be more innovative, you can do something new, something different and find a way to be successful in your role.

[00:16:07] If you have the grit to do it, I love that. You're right. It's like, it's that grit. It's that willingness to try something different. Like even with COVID. I mean, my, I think granted, I, I work for challengers, so obviously, like, I, you know, I love this, but I think one of the things that we learned was just risk aversion of the customer.

[00:16:27] Isn't an all-time high, because of course it is right. Like who's voluntarily deciding to disrupt their organization by buying something. If they don't have to, all we're doing is like preserve, preserve, preserve, like make it so nothing changes. And it's fascinating. And when you look at some of them, like [00:16:43] when we researched this stuff, it's like 38% of B2B buying decisions just end up with the customer base.

[00:16:49] I'm not gonna do anything. I'm not going to go with your competitor. You have to go with you. I'm just going to get to do anything because I don't want to, I don't want to go through it. And I think like what you described there, that grit, that tenacity to be like, I'm going to go out and challenge people and get them to think differently is such, is something we've always viewed as like, you either have it or you don't.

[00:17:05] But I think the unfortunate thing is like we, as organizations just don't tend to teach our people to behave that. Right. Yeah. I mean the hardest, the hardest sell is against the status quo, right? Like, and it's not that in a seller, it really depends on the seller skills. Like, do they have the ability to help the prospect understand the impact of doing nothing or do they not have the ability to ask the tough questions to help the prospect come to that realization on that?

[00:17:38] I love the way you put that. And it's a mindset, right? It's like if I view my [00:17:42] mindset is to make the customer feel comfortable, then I'm not going to ask those hard questions. I'm not going to push their thinking. I'm not going to expose them to risks that there are voidable that they're incurring. But if my mindset is really truly like this word, customer centric has always flown around, but.

[00:17:57] If I'm truly there as a seller to help my customer, I have to ask those hard questions because otherwise I'm just letting them sit in unnecessary cost and risk, and that's not being a good partner to our customers. But I think I talked to salespeople all the time who say like, am I allowed to do that?

[00:18:11] Am I allowed to make the customer uncomfortable? And. Why else do we, as humans change, we only change over uncomfortable. Yeah. And it's, um, it's, it's, it's such an interesting concept because there are so many people that are just overly concerned with wanting to be liked that they're not willing to make them uncomfortable or ask tough questions.

[00:18:32] Or get them to think about something they haven't considered or even tell them that they might be wrong about what they think. Um, and it's actually the exact [00:18:41] opposite. Like it is the best way to build trust and to build rapport in a relationship that you're hoping to take to the next stage of your sales cycle.

[00:18:50] 100%, some client of ours gave us analogy. I always, I use this all the time because I think it's so true. It's like when you have a bad day and you go to the. And the bartenders feeding you Drakes. It's like, man, this experience is fun. My bad day just got better. And then you wake up the next day and you have a terrible hangover.

[00:19:06] And you're just like, oh, why did I do that? Versus if you have a bad day, you go to see your physical trainer or personal trainer. Right. And they are just like, brutal on you. They are working you. And it's the last thing you want to be doing, but you walk out of the gym and you're like, I feel better than I have all day.

[00:19:20] It's so analogous with a sales rep, right? Like, yes, it might feel nice to the customer to talk to someone who's not pushing. But at the end of the day, your business is worse off for it. And so I always like that always stuck with me. I was like, that's I don't, I don't want to be the bartender. How would it be the personal trainer?

[00:19:36] Yeah. Yeah. That's a good, this good, healthy choice.[00:19:40] 

[00:19:44] I love, I love that example. I've never heard that one before. One that I've heard people say that are kind of similar, right. As people who want to be liked, they're the person that are like, not going to tell you that, you know, if you have something in your teeth, like maybe a piece of salad, you know, they're going to leave it.

[00:20:00] You know, they're not going to say anything. They're going to let you walk around with no spinach in your teeth or whatever. And the person that's, you know, willing to make you feel uncomfortable for your own good is going to be like, Hey, you might want to get that right there. You might even get, they might even get it for you.

[00:20:22] Not COVID friendly. Not COVID. Okay. So how long have you been at challenger now? And talk to me a little bit about like the work that you do there specifically. Yeah. So I started this role in 2 20 16, um, and there's been some changes. Like we were in a hunter [00:20:39] farmer role where you did both now this year, we reorg and I'm purely hunting.

[00:20:43] And so it's a hundred percent the job I love and adore, which brings me a lot of happiness. Um, and. Primarily, what we're doing is we're finding companies that are out there saying like, look COVID was a big wake up call to us. We thought we were doing well. But we realized is demand was really just in our favor.

[00:21:00] And we have a sales organization that are great order takers. They're great at building nice relationships, they're responsive, but they don't do exactly what you're just talking about. Colin. Like they don't push the customer to see. Yes, the world is scary. Yes, there's uncertainty, but there are things within your control that you are letting happen to your business that are making this problem worse.

[00:21:20] And so we're looking for those companies who were saying, we need to shift the mindset of our sellers. If we're going to be able to compete in a world where demand has been disrupted. And so once my job is really to have conversations because not every company is in that situation. Right. There's a fleet management company that I've worked with in the past where like, we, we don't [00:21:38] want orders.

[00:21:38] We don't have cars to sell. Right. So it's like, it's not for everybody, but where it's great is where you've got a company who is saying like, we've got people that have this order taker mindset. It's just not good enough, but we got to arm them to be successful. And so it's not just. Throw your sellers in a classroom and tell them something.

[00:21:55] We got to look at what the organization does to make this problem better. And so what's exciting to me is it's not just like go train people on discovery, go train people on negotiation. It's training people to have a different mindset when they approach. Yeah, I love that. I just had Fred diamond on too.

[00:22:10] And he said something interesting is like the best sellers. They're not just knowing like what, you know, their customers need. It's what they're knowing, what their customers, customers needs. I love that. I love that because that's what your customer cares about. Yeah. And I love the example. Like people can't sell cars, there's no cars to sell.

[00:22:30] Like, you know, I know, I feel for them last year were like, we can't get anyone to buy a car because [00:22:37] no, one's traveling this year. They're like, please stop buying until we have chill. I know. Yeah. I was just at the car lot last weekend and we like test drove a car and then. We don't have this car. Well, why the heck did you let me test drive?

[00:22:50] Is

[00:22:54] there like for six months or now, and you still want to buy it? Do you want to come back? Yeah, what's interesting. It's going to change the whole industry. I mean, like, I think everything, they may all move to the Tesla model where you got to wait nine months to get your car, but how bad do you want that car?

[00:23:08] How bad. Yeah, yeah, bad. I mean, if you're willing to wait like that long, we have two of them. So,

[00:23:19] um, Jen, it's been awesome having you on learning a little bit more about you and your experience. Um, any final thoughts. What links are we going to drop in the show notes so people can get into your world if they want to. Well, first of all, thank you for having me on this was honestly a [00:23:36] lot of fun and I know that was your goal setting out.

[00:23:38] So I certainly had a lot of fun on this. Um, I think there's probably two links that we'll share. So one is every month, every first Thursday. We're on the phone, talking to people about how you execute this type of mindset in the moments that matter, like the negotiation, the first call, the demo, the discovery, all that stuff, that's all free and available for anyone to see who's struggling with those areas.

[00:23:57] Like I said, like I was that's one and then we do, uh, we also do a podcast where we just talk about just more conversationally like this and have some guests on. So we'll probably drop those in the link. But again, thank you so much, Colin. I love the work that you're doing and I'm excited to have been a part of.

[00:24:12] Awesome. Thanks so much for coming on. We will include those links for everyone in the show notes so you can check them out. For sure. If you enjoy today's episode, please write us a review. Share the show with your friends really does help us out. And as always, we are listening for your feedback. Hey, you stuck around that tells me you're serious about your own sales transformation.

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