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Q: Who is Jen Allen-Knuth?

Jen Allen-Knuth is the founder of DemandJen and a sales trainer who headlines sales kickoffs. She spent 18 years in enterprise sales and rose to chief evangelist at Challenger, the company behind The Challenger Sale, before going out on her own.

Q: How do you build an audience on LinkedIn as a salesperson?

Jen grew past 100,000 followers by dropping safe, generic posts and sharing honest opinions instead. Her advice is to stop trying to sound smart, take a real point of view, and show up consistently as yourself.

Q: What makes sales training actually stick?

Jen argues that training works when it is grounded in real accounts rather than theory. In every session she runs, people apply the lesson to live deals and leave with a concrete next action, like an email to send or a call to run.

Full Transcript

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Rustin Schroeder · 00:00Welcome to Training That Works. My guest today is Jen Allen-Knuth, founder of DemandJen. She spent 18 years in enterprise sales and closed over 50 million in revenue to C-level executives. She rose to chief evangelist at Challenger, the company behind the Challenger sale. And she grew their podcast from 2,000 to 20,000 listeners a month. But she walked away from all of it to build something on her own. Today she's one of the most in-demand keynote speakers and specializes in sales kickoff events. Jen, welcome to the show.

Jen Allen-Knuth · 00:31Thank you so much. And we were joking before, you got my name correct on the first try, which no one ever does.

Rustin Schroeder · 00:36Fantastic. So hey, can you tell us a little bit about yourself? And when someone asks you kind of outside the industry, hey, what do you do for work? How do you explain that?

Jen Allen-Knuth · 00:41Yeah, it's funny. I don't try to overcomplicate it or make it sound sexier than it is. I'm usually just like I'm a sales trainer. It's not what I thought I would be doing at this point in my career, but effectively that's what it is. I never thought I would be doing this because I thought I would be an individual contributor forever. I stayed an individual contributor for eighteen years because sales never was actually that easy for me. I felt like every year there was a new change in the environment with the buyer, with technology, something that made it harder. And so I was very lucky to grow up inside of organizations where I had great coaches, great training, great enablement. I think I just sort of fell in love with the fact that anyone, in my opinion, can become a great seller if you have the will. And eventually a lot of my high came from watching other people realize their potential.

Rustin Schroeder · 01:41And so you were doing this for eighteen years. What was the catalyst, or what was the reason that you decided, I'm gonna try and do something on my own? That's a huge milestone in someone's life. Can you paint us a picture of what that looked like?

Jen Allen-Knuth · 01:56Yeah. And first, let me throw myself under the bus. I went out on my own. I chickened out. I took another job. So I would love to be like, I worked up the courage. But my last year at Challenger, I was carrying a bag still.

Jen Allen-Knuth · 02:09But I took on this role of chief evangelist where I started doing the podcast, started doing webinars, and started getting on stages. Clients would have me come out and do the kickoff to Challenger. And as I did more of that, I realized, man, this is so fun. This is the thing that lights me up. Every couple years across my career I've had this moment of reflection where I start auditing what are the things that light me up and what are the things that suck my energy. I realized being on these stages, working with different sales teams, that was the thing that was really lighting me up. So in December of that year I was like, I could keep ignoring it, or I could go off on my own and do it full-time. I was very lucky to have been afforded the opportunity at Challenger to test the waters. So I quit in December. And then I had another company call me very early in January and said, Do you want to do this job?

Jen Allen-Knuth · 03:09And I was like, could I still do this on the side? They were very open to it. And nine months later, I was like, listen, this thing is still pulling me. And that's when I went full time. So I chickened out for sure.

Rustin Schroeder · 03:12Wow, that's really cool. But the fact that you did it is huge. Can you walk us through what it was like when you put in your two week notice? What did that feel like, saying, All right, I'm gonna try and do this on my own?

Jen Allen-Knuth · 03:48Absolutely terrifying. I think it is very difficult when you attach your worth to a brand. I was lucky to work for a great brand in Challenger. I was lucky to work for a great brand in Lavender. I had attached myself to these great brands. And the hesitancy on my part came from, what if my value is because I work here? If you were to have called me the morning that I gave my two weeks, you would have seen me in a completely panicked state, still second guessing. I was just very lucky to have a few people close to me push me to say, look, if it doesn't work out, you can always go back to being a sales rep. You will not have a hard time getting hired. I felt like I needed a safety net, and I didn't feel like I had one until someone held up the mirror and said, you're making this a little bit more extreme than it is.

Rustin Schroeder · 04:36Right. And did they keep you on for that two weeks?

Jen Allen-Knuth · 04:41Yeah. I'm a big proponent that you never leave someone high and dry. A lot of the relationships I've built over my career have been people that introduced me to customers and prospects. You never ever leave on bad terms. Even if you're unhappy, it's too risky, and you don't want to give people a reason to second guess your qualifications or your ethics.

Rustin Schroeder · 04:56Right, for sure. And what did it feel like when you left for that last day at work? Were you in the office?

Jen Allen-Knuth · 05:12So weird. No, I was at home, and that's actually a really interesting question. When you leave a job and you're packing up your box and going out the door, it feels very final. But for this, I'm like, okay, I'm just shutting down my laptop and all of my stuff is gonna be turned off, but nothing else changes. That's a very bizarre feeling.

Jen Allen-Knuth · 05:37My husband was like, we're going out for margaritas. We have to make it feel celebratory. So that's what we did instead.

Rustin Schroeder · 05:41So it was just close the laptop and you were done. I had worked in the corporate world for 22 years, and I had a sabbatical after seven years. When I left, I was gonna be gone for 12 weeks. I was getting married on a Sunday and going on sabbatical that Monday. I remember walking to the car thinking, wow. So great that your husband made you go celebrate. On your website, you say you've made every mistake in the book as a seller. When you transitioned from seller to founder, what were some of the early rough patches or hardest lessons?

Jen Allen-Knuth · 06:13Oh my goodness. The biggest one was the importance of having a great accountant. I had kept an accountant that had done my taxes when I was a W-2 employee. Two things I should have done differently. One, I should have pressed harder on whether he had other people like me that he was working with, to understand the intricacies of those tax situations. And two, I should have gone to my network of other people that do this job and asked, what are you doing? Who are you working with? What are the pitfalls to watch out for? That is easily, by a mile, the thing I screwed up the most, and I ended up having to scramble. Whenever it comes to taxes or money, you never want to be stressed about that while you're already stressed about building a business.

Rustin Schroeder · 07:17Right. You don't want to be caught saying, wait, I owe someone money. That's a headache you definitely don't want. So I want to go back to the stages. When did you realize that sales kickoffs were the perfect business to build around?

Jen Allen-Knuth · 07:31Before I realized it, I always assumed that to earn your spot on a stage at a sales kickoff, you had to have a book, you had to have some career story of exits, or you had to climb Mount Everest. So for most of it, I really just didn't think it was possible for someone like me. When I was at Challenger, through the chief evangelist job, they were bringing me in because clients were just starting an engagement and wanted someone to get people excited about the change.

Jen Allen-Knuth · 08:24I realized, man, I love this, and the people I'm speaking to love it. That built my confidence. But prior to it, I literally just thought it was not a possibility for me because I didn't have the resume or the professional speaking credentials. In the end, that became my unique differentiator: I am just like you. I was sitting in the same seat you were for 18 years, sitting at all of these kickoffs, hearing the messages where it's like fingers pointed at you. Why can't you just? And so that's what shaped how I approach these. I am one of you. I had the same thoughts and beliefs. And then I learned something different. That's the relatable component.

Rustin Schroeder · 09:08I really like that, because I agree. You're just like them, so you really connect with them. And that leads to my next question. You have over a hundred thousand followers on LinkedIn. That's a crazy number. You built this massive audience, even on the Challenger podcast. Practically speaking, how did you do that?

Jen Allen-Knuth · 09:40I would love to be like, I did it. So I think there's three things. So number one,

Rustin Schroeder · 09:41Here's step one, yeah.

Jen Allen-Knuth · 09:49I was very lucky when I first started posting. There was a guy who's big in the sales space too, his name is Josh Braun. When I first started posting, I was posting very safe things because I was scared of someone coming at me saying, you're wrong, you don't know what you're talking about, and being publicly embarrassed. So I was posting research stats, all smart stuff. He reached out and said, I keep seeing your content, you're posting really smart stuff, but you have all these years of sales experience. Why don't you have an opinion about anything? And I was like, oh my god. It's a hard thing to hear, but he was right. I told him my fear. I'm a big tough love person. I had this conversation that was like, I'm scared of people thinking I'm an idiot. And he was like, okay, so what if they do? Then what? I didn't really think past that. He helped me realize that if you wanna be someone that is memorable, you have to have an opinion and speak honestly, not just try to sound smart. He helped me craft a voice that was about who I was and owning that, instead of trying to be this smart person on LinkedIn. That was number one.

Jen Allen-Knuth · 10:57Number two was the Challenger podcast gave me an audience I would have never had on my own. A lot of companies going through the Challenger sale methodology would tell sellers, you have to watch this podcast once a week. So it built up a really nice audience from within Challenger clients. And number three was working for Lavender. When I joined Lavender, they were in the heyday of being a social media love child. Challenger was largely manufacturing, financial services, insurance, traditional industries. Lavender opened the door to tech, and I didn't really have a tech network at all. So I attribute a lot of my growth to being at the right place at the right time and being afforded these opportunities. And then I was just really diligent about making the most of it: showing up regularly, speaking like me, not like someone else, and having fun with it too.

Rustin Schroeder · 11:59When you made your first post that wasn't stats, what was that feeling like?

Jen Allen-Knuth · 12:11Josh had encouraged me. He said, write about something that freaks you out. I had just actually lost my dad. I was like, this is something that's so hard, I haven't even told all my friends yet. I thought, if I'm gonna rip the band-aid, I'm gonna rip it way off. It wasn't meant to be a sob story. I realized in retrospect how much of my work ethic had come from my dad. So I wrote a lot about that, and how as a woman in sales that's helped me, and how to lean into it.

Jen Allen-Knuth · 12:41If I'm gonna do it, I'm just gonna go right into it. And I got a wonderful reception from people. It showed me you can make these connections, and people can connect with your message. It's not just a one-way static environment. It was very scary to do that.

Rustin Schroeder · 12:59That paved the way for you to stop saying, I'm the expert, and just be real. That's why people connected with you. So you've seen a lot of trainings, and done plenty of them. What's the best training you've ever had, and what made it great?

Jen Allen-Knuth · 13:14Probably the first time I went through Challenger, because what I really liked was that it wasn't do this process, check all these boxes, fill out this sheet. It was really more about how I thought. It confronted a lot of the assumptions I had about sales, about the things I was supposed to be doing. Where I fell in love with training was there, because I realized training doesn't have to be this rigid thing. Really good training holds a mirror up to your face and gets you to confront why. Why do I think this? Why do I believe this? How is this belief showing up across all the things I'm doing? I left that room saying, a lot of the beliefs I've held to be true, I don't even know where they came from, and why do I still hold on to those? It made me excited to go out and apply it.

Rustin Schroeder · 14:11On the opposite, what's the worst training you've ever been in? You don't have to name names.

Jen Allen-Knuth · 14:19I won't name names. It required filling out a colored piece of paper with a lot of information in the classroom that I knew the second I left I was never gonna do unless someone said you have to. It felt more like a compliance activity than truly making me more skilled at my job.

Rustin Schroeder · 14:33Right. The Challenger sale had a big impact on you. Outside of that particular book, what's your favorite business book that changed how you think?

Jen Allen-Knuth · 14:54Oh my gosh. It would actually be a more recent one. I'm not a big sales book consumer because I love learning experientially. I love when someone's teaching me and we're working on real deals. But Todd Caponi wrote a book on negotiation, and I'm probably botching the title. Sorry, Todd. What I love about it is its simplicity. It's not overly engineered. He breaks it down into basically these four things you can do in a negotiation to trade with your customer. I'm very drawn when someone can take a complex, scary thing like negotiation and make it feel simple, make it feel like, okay, now I know which levers to pull.

Rustin Schroeder · 15:41The simplicity piece definitely hits with me. That's why I love Donald Miller and his work, because he's always talking about that. So this is one of my favorite questions on the podcast. What's something about your journey that most people don't realize?

Jen Allen-Knuth · 15:47I would say I wasn't someone that made President's Club every year. My resume going into this is not, I was number one every year and that's why you should work with me. It actually comes more from the fact that I wasn't number one every year. I was always very intentional about learning why I didn't make it to number one and what I could do differently next year. I was always obsessed with figuring out what I'm doing wrong, not pointing the finger elsewhere. That's why I can be relatable, because I can understand why a seller might believe something, because at some point I probably shared that belief too. A big part of change management is you've got to get someone off of why they're currently doing what they do before they're ever open to change. I'm not very shy about saying I'm not an 18-times President's Club winner. I think I made it like three times. I was often very close, but I wasn't number one. But that's part of what makes me so excited about what I'm doing now, because I can look back and see all the mistakes I made. They were avoidable.

Rustin Schroeder · 17:08Do you still get nervous going up on stage? You've done this a lot. Are you still really nervous before you go out?

Jen Allen-Knuth · 17:16A thousand percent, because sales is a tough audience. Sales will let you know if they're like, this ain't it. I put a lot of pressure on myself, because the cost of a salesperson's time is so significant. I really value a seller's time, and the thought of wasting five minutes of their time makes my skin crawl. So I put a lot of pressure on myself right before I go on stage. Then usually five minutes in I'm like, whoo, now we can have fun. But I'm always nervous.

Rustin Schroeder · 17:17That's awesome. Any final advice for individuals or companies working to grow their revenue or improve their training?

Jen Allen-Knuth · 17:53I would say focus on learning through doing. Don't carve out a ton of time to teach theory and process and this and that. One of the things that's very core to how I run my business is that every session I do, we have real accounts we're working on. I'm teaching, and then they're applying it, and then they're leaving the room with something to go do. Here's an email I'm sending, here's a discovery call I'm running, here's a reason this company should consider change. Looking back, that was so core to all the training that really stuck with me and got reinforced. So just make sure whatever you're doing, you're grounding it in real accounts, real jobs to be done, versus theoretical stuff.

Rustin Schroeder · 18:39That's very true. I've done my fair share of theoretical stuff, and it's like, why am I here? Could we please move to something useful. That is great advice. And before we close, I love the picture at the bottom of your website. It's got the kids and the dog and your husband, all as cartoon characters. How did that come about?

Jen Allen-Knuth · 18:45So I made the mistake a lot of us do when we start our own business and said, I'll do my own website. It looked like a fifth grader made it. A guy reached out and said, I think I could help you with your website a bit. One of the things I said is I don't want to look like every other methodology or training company. I want people to see that fun is a big component of my brand. So he brought on an illustrator, Alejo. If anybody listening wants him, he's fabulous, brilliant, I adore him. He said, I'm gonna go through your Instagram and pull out components of your life, and he did that picture. I was like, this is potentially my favorite part of the whole damn website. I want people to see that I am a real person. I am not a figure. I have a family. I have interests outside of sales. He did a brilliant job of that.

Rustin Schroeder · 19:52I agree. When I saw that I was like, wow, that is real. It separates you from everybody else and gives you that feel of, this person is someone I feel like I know, because they've shared a piece of their life. So where can people find you if they want to reach out?

Jen Allen-Knuth · 20:00Yeah, so LinkedIn, I spend way too much time on there, Jen Allen-Knuth. Or my company page is DemandJen, that gets way less love from me. And then my website is demandjen.com.

Rustin Schroeder · 20:20All right, sounds good. We will definitely link to that. And thank you very much for joining the Training That Works podcast.

Jen Allen-Knuth · 20:26Thank you so much. It was so nice chatting with you.

Jen Allen-Knuth

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