Benjamin Ard (00:55)
Welcome back to another episode of Content to Close. And today I am joined by Jason. Jason, welcome to the show.
Jason Gwilliam (01:02)
Hey, Ben, nice to meet you. Happy to be here.
Benjamin Ard (01:05)
Yeah, Jason, I'm excited. You have an amazing career in enablement and sales across the board. Before we dive into today's subject, let's let the audience get to know you and your background.
Jason Gwilliam (01:21)
So I'm Jason and I'm based in Philadelphia. I've been in healthcare for 25 years. The first five years I spent working in a clinical hospital setting in the cardiac cath lab. That's where I built my foundation. A cath lab courier got me my first job in sales as a clinical or junior salesperson at a company called Spectronetics, which is now Phillips. I did that for a very short time, then they threw me into a territory manager role covering the suburbs of Philadelphia and the Lehigh Valley area. What opened my eyes was they put me in the sales role but there was like no instruction book on how to sell — it was just sink or swim. You got a number, you have a product, go out and do it. That's where the whole cold calling came into place. I was out there spinning my wheels 10 hours a day driving hundreds of miles. But working in a hospital environment and seeing hospital representatives come in — it's almost like a masterclass in what not to do. When I got into my sales role, I learned from them and also leveraged my clinical background and acumen to talk how doctors talk and understand what their problems and what our solutions were. I did sales until about 2008, only about three years, but I was successful — I went to President's Club and won awards. And then in 2008 that's when I really got into the training and enablement world. Let's be frank, in 2008 no one knew what enablement was. I got into a clinical training role, doing product training, helping the reps train, helping customers. That evolved quickly into a sales training role — again, sink or swim. What I learned was that if you want to be successful in sales training or enablement, you have to work across borders. You have to talk to marketing, salespeople, sales leadership. In med tech that includes compliance, upstream marketing, downstream marketing, leadership. From about 2008 to 2016, that role evolved into a full team running sales training and advanced trainings almost every quarter. That trial-by-fire experience really built my foundation of where I am now and why I'm talking to you today.
Benjamin Ard (04:40)
Amazing and incredible career. So Jason, today we're going to talk about how to view sales enablement as a revenue system instead of just focusing on it as a training function. How does that shift actually take place, both in practice and in the mindset of others inside an organization?
Jason Gwilliam (05:37)
That's a great question. You have to change the perception of the leaders in your business or organization, because they've used sales training or enablement as a non-revenue generating function. We don't have a quota. So how do you change that? Think about enablement at its core — it's an ecosystem. I always tell people sales enablement is an ecosystem. You have enablement in the middle, marketing, sales, upstream marketing, downstream marketing, social media, business development, all these people feeding enablement. We're more like air traffic controllers now — trying to bring the planes in and help them all land and not hit each other. There's also sales ops, the Salesforce and CRM people. What enablement is at its core: it helps sales reps sell with confidence and competence. But let's call it like we see it — we want to reduce time to competency. If I train them on January 8th, when will their first sale be? 10 days, 20 days, 40 days from now? I want someone in your team to go walk into the CFO or CRO's office and say what is the ROI on sales enablement — and then give me a call and tell me what the answer is, because no one can tell you what it is. But you look at time to competency and we did this at Abbott — if you can hire a rep and have them sell in their first 90 days, that's a huge win. If you get them out the door selling in 60 days, that's even better. It's not just about bringing a bunch of sales reps into a room and doing death by PowerPoint for eight hours. It's the tools and the plan you put together that enables them to go out and sell quicker. We want to enable them — because I worked for a company where they called it sales disablement because they didn't understand what it was at the core.
Benjamin Ard (08:21)
Wow.
Jason Gwilliam (08:27)
You can call it sales training all day long and do show-up-and-throw-up presentations — that's not sales enablement. When I worked at Abbott, as we were evolving the program, initially we had the Salesforce administrator spend an hour and a half with reps. When that program finally evolved, that went from an hour and a half to four hours. Because even the most tenured people were not using that tool as it should be used. Enablement — are we teaching sales process? Pipeline management? Qualifying and how to close? How to reduce churn? All of that. The living or dying of an enablement program starts with your key stakeholders. That's executive management. You have to sell them on the why, the how and the what, because they're the ones opening up the checkbook and writing the check for whatever software you're going to use. And they're going to want to see from day one to day 90 what kind of return they're going to start seeing.
Benjamin Ard (09:47)
When you're having those discussions and trying to change the perception and function of the enablement team to be a revenue driver — are there specific metrics you like to take to the CFO and CRO to prove the efficiency and value of the team?
Jason Gwilliam (10:10)
Time to first sale is a big one. We're looking at Salesforce metrics — how long did it take them to go from qualifying to first meeting to the next stage? We're looking at Salesforce hygiene — we taught them the sales process, but are they actually following it? Process without a plan is nothing. The big one for me has always been tying time to competency, tying the first sale. And the other piece — there's the product training component, which is also separate from sales enablement. Product training and sales enablement are not the same thing. One is how you open the cup and take the lid off. The other is talking to the customer about why your product is better and convincing them to use it. The metrics are time to competency, time to first sale, Salesforce reporting on sales cycle length. If you can take the sales cycle from 60 days down to 45, that's 15 days you shaved off — that's significant. You're looking for reproducible behaviors across the sales team, looking for consistency. Are they doing call planning the same? Are they speaking the same language about the product, features and benefits? You can build the best system in the world with the latest AI call planning software — but if you're not applying it right and positioning it right, it's all for nothing. I use a sports analogy with the VP of sales or the CRO: Michael Jordan, Wayne Gretzky, Tom Brady — they have two people they rely on, their coach and their manager. The manager says you're spending too much money. The coach tells them where they messed up and how to get better. We need coaches. You can manage them all day long. But we also have to teach people how to coach, because the best players in the world will still go back and look at film to see how they can improve. That's also a function of enablement.
Benjamin Ard (13:24)
Following that trend, and we're running out of time — in today's markets, it feels like reps aren't being hired as much and enablement teams are smaller. How has that change affected the enablement space? And how is AI fitting into your enablement stack?
Jason Gwilliam (13:54)
Two really powerful questions. On hiring around enablement — there are two schools of thought. There's the old school: sales training, spin selling, professional selling skills, challenger selling. That methodology has a purpose and I still believe in it. But the term enablement is still a relatively new term — it's like a baby as far as I'm concerned. You can go on LinkedIn today and type in sales trainer roles, a thousand will pop up. Type in sales enablement roles, maybe 30 will pop up. Do people really know what enablement is and what that person does? I view myself as an enablement practitioner because I've sold, done sales training, and done enablement. I understand the platforms, the tools, the go-to-market, how to run a sales kickoff meeting. And when I've interviewed for enablement roles and shown them what I've done, you kind of see their eyes shift and they say, I didn't realize it was this much. Alignment with marketing is so critically important. Marketing can spend hours putting together a flyer, a campaign, a message, and I'll put it in front of a sales rep and say, do you know how to use this? And they'll just read it word for word. We're enabling marketing, we're enabling go-to-market strategies, we're enabling product launches, we're enabling Salesforce hygiene. On AI — it has a place. It's not going to replace us. What AI does, it kind of validates what we already know. I used a coaching software program that used IBM Watson in its early stages. We would do video coaching, turn on the AI engine, and it would grade them — you're speaking at a first grade level, using too many filler words. It validated what we knew, but just was a little more brutal in its approach. Where it's coming to now, I was speaking to a company that does AI video analysis of customer phone calls between the rep and customer — very insightful. But we have to be careful how we position it. You don't want it to be punitive. You want it to be a tool to supplement helping reps get better. When we first started using AI coaching software back in 2018, I would tell sales managers whose reps were going to use the AI: I'm going to share the results with you, but we're going to be very careful about sharing them with the reps, because we do not want to dissuade them and make this something that's punishing them. AI is just another tool in the toolbox. That's it.
Benjamin Ard (18:39)
Yep. I love that. I think that's a great way of talking about it. Well, Jason, we have run out of time. For anyone listening, if anyone wants to reach out and connect with you online, how and where can they find you?
Jason Gwilliam (18:54)
Just go to my LinkedIn — Jason G on LinkedIn. I'm happy to talk to people. Enablement is a field that I think is growing and we're starting to see more and more interest. As a closing — I was literally talking to a company last week and I'm talking to them tomorrow — companies and startups are actually looking at fractional enablement roles now, which I've never seen before. They're looking at fractional chief operating officer roles and now fractional enablement roles to sit on boards of companies. That means people are paying attention to it.
Benjamin Ard (19:15)
I love that. Makes perfect sense. Jason's LinkedIn profile will be linked below in the show notes. Jason, thank you so much for the time and insights today. This has been awesome.
Jason Gwilliam (19:24)
Thank you.
