Benjamin Ard00:00 — Welcome back to another episode of Content Amplified. Today I'm joined by Jason. Jason, welcome back to the show. How are you doing today?
Jason Gwilliam00:07 — Good. I'm ready to talk more about enablement and content and how we make this go bigger and wider with our peers.
Benjamin Ard00:14 — Love it. Jason, it's so exciting to have a guest come back on the show. Really impressed with what we talked about the first time around. Excited to dive into it again. But for anyone who didn't listen to your episode, give us a short summary of who you are, work history, background, all that kind of fun stuff.
Jason Gwilliam00:28 — Yeah, so Jason Gwilliam. I live in the Philadelphia area in a town called King of Prussia outside of Philly. I've been in the healthcare medical device space now for, gosh, 21 years. It feels crazy to say that. I have sold for large companies like Philips. I've worked for companies like Abbott and Siemens. I've been really what I call a sales enablement practitioner and architect for almost eighteen years now, since 2008. But where I like to think I'm an expert is at the crossroads of selling and training, because true enablement people in the med tech space, in order to be successful, you have to have, they call it carrying a bag. And so I've carried a bag in numerous roles. And really that gives me a perspective on the challenges of what people have in the field when they go out and sell. Because as I've written on my LinkedIn notebook series, selling in 2005 is not the same as selling in 2026. And so you have to be able to really understand what's happening in today's market to be successful.
Benjamin Ard01:25 — Love that. That's exciting. So we're gonna dive in. This is really cool. What we're focusing on, and Jason, you had this really cool line in the email that you sent me. Content doesn't close deals, conversations do. So let's start off. What do you mean by that? What's the premise? Where did this come from?
Jason Gwilliam01:41 — So in my experience, in enablement at any level, at any company, they really need to partner with marketing and business development. And we know, especially in the med device world, that we're heavily regulated. You just can't create marketing material and collateral and go, here you go. It takes sometimes months to get a pamphlet approved. And then oftentimes they'll just put it out there and say, okay, here's a new piece on how to sell this widget. But if you don't teach them how to sell to that or speak to that, it's all for nothing. So what is the message? Who's the customer? What's the target? What is your call to action? And that's so important. So in the world that we live in, conversations close deals, whether it's 30 seconds or five minutes. And I think you'll agree that oftentimes conversations don't happen planned. They happen in an elevator, they happen in a hallway. And if you think about data and articles that are written on this topic, there's an article in Harvard Business Review called The Art of the Elevator Pitch. And what they say is that Hollywood screenwriters walk into a room, you and I are producers, we're investors. Those people will know within five to ten minutes if they're gonna invest in your project. So the message, the conversation, is important. And that Harvard Business Review article on The Art of the Elevator Pitch applies to everything that we do in our lives. Whether you're selling a computer, software, retail, manufacturing, med device, those investors, that customer is gonna know in the first couple of minutes if they want to listen to you or not. And again, data from challenger selling says customers are looking for two things. They want an insight and they want differentiation. The insight is something they didn't know about their business that you're gonna teach them. And the differentiation is, we have three products that are just like yours, what's different about yours? So that's the conversation.
Benjamin Ard03:24 — Love that. Okay, that makes perfect sense. So where does content actually play a role? I mean, obviously you're in a space where it can take a long time to develop this content. How can content aid in the conversation? What role does it play? How should we start to shift to this mindset that conversations really are the most important part of closing a deal and a sales process?
Jason Gwilliam03:44 — Yeah, I think the content is important because it can back up the conversation. Because again, in the world I live in, we call it a scrub sink story, where you're outside the operating room and you have 30 seconds to talk to a doctor about this is my product, but then you leave them the content. You can leave them a piece of collateral as the follow up. So that's where it plays a role, because you can have that quick conversation, but you need to reinforce it. And that could be a PowerPoint, it could be a brochure, it could be a data piece, because a lot of times you have maybe 30 minutes, 15 minutes, or even five minutes, or again, that elevator, you're up and down on the elevator talking to somebody. You could say, hey, remember this conversation I had with you about this product I'm trying to get you to use? Well, I'm gonna leave this with you. That way, if you have more questions, I can follow up with you. So content backs up the conversation, if that makes sense.
Benjamin Ard04:29 — Yeah, I love that. So it's the proof points, it's the follow up, it's on their own time, it's the asynchronous part of the conversation. Because it sounds like in this world, when you're using that content to kind of aid and be a help to the conversation to improve it, how do you synchronize the content with the conversation? Is this a training piece? How are you getting people involved? What does that look like to make sure all of that's in harmony and sync?
Jason Gwilliam04:58 — Yeah, when you think about it from a pure enablement lens, I was literally just talking to somebody about this a few minutes ago. There are many layers of enablement when you bring in people to train, because it's not sales training anymore, it's enablement, because we're enabling them to go out and sell and generate revenue. But to your point, it's the art of storytelling. How are they telling the story? How are they delivering the message? How are they articulating it? Because I can hand you or my son a brochure and you can read it word for word. Anyone can do that. But how do you position it? How do you digest it? How do you deliver it is key, because you don't have 20 minutes to read through the brochure, you have to deliver three key points. So what are the takeaways you want to leave your customer with? Because every customer is different. What my important things are are different from yours, right? And so you have to be able to focus on that and understand the customer in order to do that. So when you're going through training or enablement, we spend a lot of time on messaging, positioning, value prop. And honestly, I may have said this in a prior podcast with you, but the one thing I tell sales leaders is read the book by Simon Sinek called Start with Why. Why? Why your product. And I'll challenge reps and go, if you can't tell me how, why, and what, there's my door. When you know those answers, come back and tell me. I know it may be a little direct, but in the world we live in today, you got to back up things and you have to be succinct. You just can't ramble on.
Benjamin Ard06:23 — Well, it's fascinating you're talking about this as we use AI more and more nowadays. I have actually built into my AI to say we have to nail the story, like you're talking about the why, before we can ever build any collateral, website pages, or anything at all. If we haven't agreed on the story, the AI and I, there's nothing to build yet. And it's kind of fascinating. You're treating that same process with humans. If you don't know the why, if you don't know the story, the content can't save you. Nothing can save you in that process.
Jason Gwilliam06:59 — Yeah, and that's actually a really good point, the AI piece, because customers are more educated and informed now than ever before. They're using AI whether we like it or not. And not that AI is replacing us or you or me, but it is an information repository. Is it right? Most of the time it is, but you can guarantee that they're looking at X versus Y for competition. They're doing their due diligence. So it's now more important than ever to be educated and to be able to deliver a message that's gonna resonate with the customer to move the needle.
Benjamin Ard07:29 — So one thing that you also mentioned in our emails going back and forth for the discussion today, and this is something you're an expert in in training, you mentioned the analogy of athletes reviewing film and musicians rehearsing. I really love this. So how does this analogy apply to this conversation today? And I want to push you a little bit on it. I'm going to throw you a curveball here, not only for a sales team, but how can other individuals, say marketers and other people in a company, apply the same principles here of an athlete reviewing film or a musician rehearsing their whole performance? What does that look like and how can people really do that?
Jason Gwilliam08:07 — Yeah, it's really not a curveball, because it's something I've been kind of practicing for a long time in my enablement world. And the reason why it's not a curveball is because there's a couple of analogies I can use. One is I will go to a sales team and say, do you wanna be comfortable or do you wanna be ready? Because they're not the same. And there was a performance coach named Dave Alred that actually used that principle for a golfer for the British Open. The golfer had a great long game, but his short game was horrible. So he focused on the short game, and guess what? He won. So you have to focus on being comfortable or being ready. A lot of reps are comfortable because I can do this, I can do that, but are you ready for competition? Are you ready for the pushback? And then if you want to connect the dots, the book Outliers by Malcolm Gladwell, he talks about the 10,000 hour rule. Are you spending 10,000 hours being better at what you're doing? Refining your craft. Tiger Woods, Michael Jordan, Tom Brady. Brady could have the best game in the world when he was on the Patriots, but Belichick would pull him in and he would sit down with the quarterback coach and go review film to see how he can get better for the next game. Do you think he won seven Super Bowls for a reason? And again, the point is that when you connect the dots with athletes, sales reps are the same way. You have to practice to get better. What's your message? What's your pitch? And so coaching, reinforcing, mentoring, those things are very important in all things we do. And even with marketing and content, to your point, because again, are reps comfortable delivering the message or are they ready to deliver the message? Because they are two different things. Again, comfortable is I can read it verbatim. Ready is tell me the top three things in that without looking at it.
Benjamin Ard09:44 — Yeah. I love that.
Jason Gwilliam09:45 — That's why I always connect the sports analogy, the 10,000 hour rule, because those are real world scenarios that are done every day. You look at hockey with the Stanley Cup playoffs right now, the Hurricanes and the Knights. You better believe after every game that coach is in the locker room telling them, we won, but if we wanna win and get the cup, we gotta keep practicing and getting better.
Benjamin Ard10:06 — A hundred percent. That's a painful subject right now because I'm a Utah hockey fan and we lost to the Knights barely.
Jason Gwilliam10:09 — Well, I know, but look, it is painful for me too. The Flyers lost against the Hurricanes. But anyway, my point is that there are articles and studies out there focusing on those things around being comfortable versus being ready, the 10,000 hour rule. And honestly, I didn't believe in any of it until I started reading it. And then when I started talking about it to sales leaders, guess what they did? They leaned forward and said, tell me more.
Benjamin Ard10:35 — Yeah, I love that. Now AI is kind of changing the game here. So we have this whole system of conversation intelligence. I mean, every phone call feels like it's recorded. You can't be on a phone call without half a dozen note takers on it, it seems like. How is that becoming the game film? And how do you best actually use that material on all sides of the business to really review, refine, improve, and progress?
Jason Gwilliam11:00 — Another great topic. So when I was working for another company in 2018, we were early adopters of AI video coaching. And you can imagine in 2018, when you mentioned the word AI, it was like you were calling someone a four letter word. And so you have two challenges with AI. One, you can't BS it. I'm not gonna say the word, but you can't BS it. And AI is gonna give you direct feedback. It's not going to tell you you did okay. It's going to say you're good or bad. And so that is important to understand, because if I'm your manager and I do a ride with you in the field, my feedback is gonna be dramatically different than what AI's feedback could have been. If I'm shadowing you on a sales call or I'm on a Teams call listening to you talk to a customer, I can say, you know what, Ben was having a bad day. The customer was in a bad mood. Let's try again next week. AI is going to be like, hey man, you're speaking at a fifth grade level. You're talking too fast. You're using filler words. And that can come off as punitive, right? Where the manager's feedback could come off as more of, here's the feedback and let's try again next time. So I think we have to be able to understand, again, the how and the why, how AI is being used and why. And I think if you position it as a coaching tool and don't make it punitive, it comes across much better than you're good or bad. And it is an improvement tool. And again, when I was using AI in 2018 for video coaching, it was IBM Watson. That's how old it was. That's gone now. It's Grok, it's ChatGPT, it's whatever AI engine is being used now. And so when I talk to companies about this, I'm like, listen, this is a great tool. But reps have to be comfortable turning it on when they're having that sales call and having confidence that they're not gonna get fired for this. It's no different than the game film, to your point. We're just looking at film going, how can you get better? And it is intimidating. As someone who's been using it now for eight years, I'm still intimidated by it, but I'm also excited to see how far it's come. But at the end of the day, I see companies leaning into it more, but I also see companies taking a wait and see approach because they don't want to scare people away or they don't want to replace a current system they have in place. So my philosophy on AI is that it's here. We can either lean into it or we can go, nah, this is never gonna happen. So my conversations with leaders around AI is, listen, this is a tool out of the many tools we have in a toolbox, and we wanna use this for reps to help them upskill. We're not gonna take the worst AI video coaching and post it on YouTube for the world to see. Right? We're gonna use it as an opportunity to improve and get better and not punish.
Benjamin Ard13:35 — Well, and I want to hit on a couple of those points because I really love what you're talking about here. First of all, AI out of the box is overly complimentary. It's really like, you're the greatest thing in the world, Ben. This is the coolest idea. Man, you're gonna make billions of dollars. You have to train your AI to give you honest and critical feedback. The second thing I love that you're talking about is you are encouraging everyone, regardless if you're in sales, marketing, otherwise, as you're improving your craft, getting honest coaching and feedback, you have to have a level of humility. You have to go in and say, I am coachable, teachable, and understanding. But the only time that people can feel comfortable with that, and you hit on this, and I want to dive into this as well, the company isn't going to punish you. You have to have this culture of AI and teams are going to teach you where you need to improve, where you're weak. You're going to be humble and admit it and get better. And we're not going to punish you for it, because there are cultures where people feel defensive because they're afraid any sign of weakness is an opportunity for them to get fired. How do you develop this culture both on teams to be humble enough to actually listen to coaching and feedback and take it, and then also from a leadership perspective to encourage individuals to say, weaknesses are not a reason for firing. We have to create this environment of we're making people better and it's okay to have weaknesses.
Jason Gwilliam15:00 — Yeah, so a few things on that. With AI now, especially when you're talking about more of the coaching side, not like generic ChatGPT out of the box or Grok, you can actually tell it what to measure and what to evaluate. So you can say, measure their cadence. Are they talking too fast, are they talking too slow? You can program it to highlight keywords or filler words. You can program it to say this person only has five minutes to talk, but they spoke for 10. So you can proactively program it to have certain parameters, to your point. The other piece that I would say is that it has to be positioned in a way as a development tool and a coaching tool. And again, this is something I wrote about, is that reps, whether it's retail, industry, SaaS, med device, there is a huge generational gap right now between Gen X, which is me, and millennials.
Benjamin Ard15:51 — Which is me.
Jason Gwilliam15:53 — But my point is that I have trained Gen X reps that have been selling for 15, 20 years. They walk into a room like, why am I here? What I'm doing is already fine. And I'll go, listen, pardon my language, but hold my beer for a minute, because the way you sold in 2005 is not how you're selling today. And if you're not adapting to that, we have a problem, my friend. And I'm not here to tell you what you're doing is wrong. I'm here to tell you I want to help you succeed. And that humility piece is important. And embracing technology is a part of that curve. And the days of answering a page and going to a payphone and dropping a quarter is over. It's text message, it's video Teams calls, it's FaceTimes. And so if you're not comfortable with any of that, there's a problem, because that's the way the world is going right now. You can probably poll 10 reps and say, how many sales calls do you have in person versus what we're doing right now? And they'll probably say it's 50-50, 60-40. But my point around the AI piece is that we are able to program it to give the feedback we want it to give. And that is key, because when you talk about leadership, marketing, we have to be aligned to stakeholders on what we're actually measuring and what we're trying to get out of it. Because if you don't do that, you're kind of just using a great tool for nothing.
Benjamin Ard17:05 — Jason, we're out of time, but I do want to ask one final question. I love to end these podcasts with tactical advice. So for anyone listening today saying, yep, we need to up our game here, what would you recommend they could do starting this month to improve, whether it's coaching, their usage of AI, how they utilize content? Anything along those lines where you can say, yep, I would start here. Anything that comes to mind.
Jason Gwilliam17:30 — Well, that would be another podcast, but I would say that the world is moving and evolving fast. The tools that are available now versus five or six years ago have probably doubled or tripled. I would say, if this is for sales leaders and enablement leaders looking to upgrade their program, do your homework. Make sure whatever you're bringing in is fit for the purpose you need it for, because these are significant investments. And once you make the investment, it's kind of hard to go back from that. But really, we have to work together holistically as a team, marketing, sales, training, to understand what our goals are and really march towards that. And what tools can we use in the AI SaaS toolbox that are gonna help us get there? Because you can't do this in a vacuum, and you have to really, again I'm gonna use the word holistic, but it has to be a holistic approach. It can't be my idea or Ben's idea. It has to be a team idea. And then the current role I'm in, what's refreshing is that's the approach we're taking, is that let's look at what's available and then decide what's best.
Benjamin Ard18:34 — I love it. Jason, again, thank you for coming on the podcast the second time. This has been a great conversation. For anyone listening who wants to reach out and connect with you online, how and where can they find you?
Jason Gwilliam18:45 — Well, obviously on LinkedIn. Jason Gwilliam on LinkedIn, or maybe Jason G on LinkedIn.
Benjamin Ard18:50 — Love it. For anyone listening, scroll down to the show notes. You'll be able to see all the contact information for Jason there. Jason, again, thank you for the time and insights today. Great having you back on.
Jason Gwilliam18:58 — Thank you.
