The Dealer Playbook

Ep. 661 - What Agentic AI Means for the Future of Automotive Retail, with Barry Hillier

• Michael Cirillo

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In this episode, my guest is Barry Hillier, co-founder of Auto Agentic A.I. and someone I’ve known and respected for years. Barry’s got a deep background in SaaS and marketing, and he’s one of those rare people who can make complex tech make sense—and more importantly, make it useful.

We talk about what AI actually means for dealerships, business owners, and people in general—not in the theoretical sense, but in the “what should I be doing about this right now?” kind of way.

Here’s a glimpse of what you’ll get from this conversation:

  • How AI can make you better at your job instead of taking it
  • What dealerships need to know before jumping into AI tools
  • Why people with strong emotional intelligence (EQ) might be more valuable than ever
  • How AI changes the way we train, learn, and lead teams
  • What this all means for the next generation—including your kids

Barry also shares how he fell into building tech solutions for the auto industry, what he’s learned from saying “yes” before knowing how, and why we’re just scratching the surface of how AI can elevate human potential.

If you're a dealer, leader, entrepreneur—or just someone trying to figure out where you fit in this next chapter—this one’s worth a listen. The ideas we explore could shift the way you think about tech, talent, and your future.

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MC:

This episode is brought to you by FlexDealer. Hey, auto industry, what is going on? We are live here at the Toronto International Auto Show. I'm sitting down with my pal, barry Hillier. Did I say it right? I hate when I get people's names wrong. You got it absolutely right. Thank you very much, man. This is how you know the episode is just going to go is when you get the guest name right, and I have to get your name right because we've known each other for a long time.

MC:

Thank you so much for joining me on the Dealer Playbook.

Barry:

You know what, Michael? It's fantastic and you are the first person I'm actually talking to in any formal way, since I've been out of automotive since 2017. I'm thrilled that you're the guy that I get to talk to first.

MC:

Now the now. You're going to see the sweat start to roll down my face here. You are somebody that I have a lot of respect for, especially because you know, when I was starting my companies, you were the one who I was like man. He's rung the bell Like you've figured out something. You were. You're a big name in SAS and in software and finding unique solutions to the problems of the day, and so I have a lot of respect for you there, and I'm excited to talk to you about your new venture. You're the co-founder of Autoagentic AI. Obviously, you know this. That is the thing everyone's talking about, yeah, but if I think there's anybody that has a unique spin on how we should be thinking about AI, it's you. So to set the stage here, I want to just kind of backtrack rewind a little bit, of just kind of backtrack rewind a little bit. How did you even get into software? And the second to that is how do you see that all of that experience prepared you for this new venture?

Barry:

It's a great question, and the answer is every career step that I've taken I've fallen into. I haven't strategically found that direction. So, in other words, you know, when I had Dashboard, we were doing agency service work, and after the market crashed in 2008, toyota basically had said we're no longer providing our web platforms to the dealers, and I was doing a lot of work on Territory Toilet Dealers this was one of my biggest accounts, sure, and so a bunch of dealers came to me and said, hey, can you build this for us? So you know, every entrepreneur out there is going to relate to this. Of course, I said yes, I had no idea what they were asking me. I knew I could figure it out, though, and so I started to work very closely with some key individuals.

Barry:

It was actually a meme to Johnny at Don Valley North Lexus, who, originally, I started to talk with and built out the initial platform for what became Glovebox, and what ended up happening was I thought that was going to just be a way for me to get more agency service work. I didn't realize the real power of SaaS at the time, and I didn't even know what SaaS was, but the more I got into it, the more. I realized especially when all of those $400 checks started arriving each month and one month it dawned on me that's $25,000 a year and because of the caliber of what we built, it was growing by word of mouth. We didn't have a single salesperson. So Brent Weiss at the time and I started to say let's take this seriously and we really doubled down and we said we're going to pursue this as a business and build that out.

Barry:

We started to create the next version. We were, I believe, the first and I can say definitively, we were one of the first web platforms to have responsive design and that's across North America. And then Steve Southern had approached me and we created Bumper and then I created a few other platforms, but each of those kind of came about more because an opportunity presented itself. Rather than me being a tech guy. You know in my heart of hearts, cause I'm not right, but that's how that all happened and AI kind of happened the same way. We sold the companies in 2017 and I thought I was done with tech and I thought it was done in automotive.

MC:

I love. So, first of all, if I can just unpack one thing I love, you say I'm a founder, I'm an entrepreneur. Yeah, the fact that you said yes to something I don't think a lot of people understand the nuance of I'm going to say yes to something that I don't understand, and figure it out, and figure it out, because therein lies the joy of entrepreneurship. Yeah, in my opinion, and it's also great improvisational comedy, because it's always about the yes and A hundred percent Right. Yes, and I don't know what I'm doing, but I'm going to figure it out.

Barry:

One of my favorite ways when somebody asks me what's it like being an entrepreneur? And I said well, here's what it's like. You jump off a cliff and you start building a plane and you hope you don't hit the ground and you start to at least glide, if not get air, and you know at the end of the day I think every good entrepreneur realizes if there's an opportunity, nobody else is necessarily smarter or better than you. You just need to find the people and you need to find the way to make it happen. And that was exactly our approach when it came from. We're already building websites and we've been building apps, so the leap to go from that into creating SaaS software wasn't necessarily a huge leap, but it was very different. We decided to figure out how to make that work and to work at a level that we were proud of Right.

MC:

Now here comes AI, yeah, which I love talking about, because I'm the kind of guy who doesn't like to just look at a topic from this angle. My immediate response is I need to see what's on the other side of this right. This and AI is that? I like to go hold on a minute. What does it look like from the other side? And, as we were talking pre-show, it seems that since 2017, as you've really started to dig in and develop your new venture, autoagentic that that's kind of how you're approaching AI. It's less buzz and it's more practicality of it.

Barry:

For me, technology has never been about what's behind the scenes, from the standpoint of how is it built. It's always about how is it used and getting into the notion of how it's used. I've also never seen technology as replacing people, and that's a huge concern, I know. With AI, if you think about when computers came in, there was an explosion that created all these new jobs, so there were far more people that had careers post-computer than when you think about even simple things like checkouts. Well, all of the stores weren't reducing the staff, they just shifted them, and so on and so on. And so, to me, ai. In my heart of hearts, I believe this AI will always beat people, but AI with people nobody can touch, because you have the EQ of the person and you now have the potential of AI to elevate the potential of the person.

Barry:

And I think what ends up happening is and I'll use a different example from the standpoint to make this point yes, we're going to lose certain careers. If you are a copywriter, you are going to find yourself in trouble. If you are a musician, you are going to find yourself in trouble. Great musicians will still find a way. But here's the flip side People that may not be great musicians or they may not be great writers, are going to be able to tap into AI. So that very large group that has creative potential but couldn't realize it are going to rely on tools that are going to allow them to actually be better versions of themselves.

Barry:

And so now you factor that into entrepreneurs, who can't necessarily compete with the large guys, they now have tools at their fingertips to be able to do things that they couldn't have afforded to do, they didn't know how to do before, and so to bring it back into automotive dealerships. And there's a really interesting example that somebody asked me and he says okay, well, what about a new salesperson walking in to be a better salesperson, to have better listening techniques, to do product knowledge tests, to understand, you know, I'm a 20 some odd year old. How can I talk to a 45 year old mother of three and do that in a way that actually is going to connect with her? These are the things that these tools are going to allow, that I think are going to not replace anybody, but they're going to bring out the better versions of ourselves and in doing that we're going to see the entire workforce change. But I'm not a believer. That's going to change for the worse, at least not for everybody. Some people are going to get devastated. I'm not going to lie.

MC:

I mean, while you think to your point about the copywriter, you know we only know the George Jetson that pushed the button for the sprockets. Yeah, but 20 years earlier George Jetson was building the sprockets by hand, so his job got resorted to. I'm just making this is a, you know, total, fictional analogy.

Barry:

But it's a fair one, because when you sit down and you take a look at, you've got a lot of individuals and what I would say, regardless of where you're sitting, you know, is AI a friend? Is it a foe? Is it a mistake? The more that you embrace it, the tsunami is. You can see the crest, it's here Right. So are you going to embrace it to understand enough so that you're not sitting on the beach when that tsunami hits and that tsunami isn't gonna stop? You know, remember how many people I can't tell you how many times when I would present to dealerships this new thing called the internet and we don't need a website, or hey, now there's this new thing called social media, and literally had people say I don't want, I don't care what somebody had for lunch, and yet these did have a lot of negative elements about them, but they also had a lot of positive, and there were windows when the people that weren't using them really they got hurt, and AI is that on steroids right now.

MC:

So, when it comes to your position, the solution that you want to bring in, that you know. I love how you're saying when it's connected to human, yeah, it's unstoppable.

Barry:

So, with what you're working on, what is the position or the message that you want the dealer body to understand or to know? My position, when it comes down to the dealer body, is educate yourself and educate yourself. Like so many past technologies, you had situations where people were misrepresenting themselves, they were putting lipstick on a pig, they were over inflating what something would do. Really educate yourself as to what is actually happening to enough of an extent that you're asking the right questions about security, about what are the foundations of their approach. So, whether it's different large language models or whether it's different ways that they're constructing these, it's really important that you start to understand enough of the basics. And the crazy thing is, any dealer can go out there and just ask chat, gpt, explain these things to me in a way that I can understand.

Barry:

So don't dive into the old bullshit. Baffles brains. You know kind of tech approach, but really understand some fundamentals of something that is going to radically alter not just your business but think about for you know, dealers that have kids out there, this, too how are you going to help your employees be guided through this? And if you're being assertive and you're taking control of understanding as much as you can. You're not going to be sitting on the beach anymore right, it's interesting you bring the kids into this.

MC:

I'm old enough, a millennial, to have enjoyed mash on tv, yeah, and young enough to be hip with the Fresh Prince crowd, you know. And what I realized over Christmas when I did a complete 180 and my wife and I decided to get our kids phones we had held I mean, my oldest is almost 16. Like, we've held off on the whole phone thing, wow, good for you. I was driving one day and it hit me and you just struck this again in me. But they're the first generation who will never not have this thing. Yeah, I remember, you know pagers.

MC:

I remember the look on my grandfather's face when my dad pulled out his first cell phone that was as wide as this. You know he had a briefcase for this A briefcase was his phone case and watching what looked like the ghost. Leave my grandfather's body, but it it progresses from there. Well, if I don't teach them how to use this thing, which is now pre-loaded with, yeah, siri speaking to gpt, and if I don't help them understand how to prompt it to enhance their human capabilities and understanding, then who's going to do it? A college roommate, and it dawned on me what you're saying the tsunami doesn't have to be a lethal visual, but to me the way it becomes practical, barry, is oh, this is the world my kids will always live in.

Barry:

A hundred percent and I'm actually I'm going to build off of this because one of the things that I found interesting, we were the generation so I'm just a little bit older than you and going in the early days, you had 20s and 30-year-olds who, basically, were creating the rule book of UI, ux and internet and e-commerce. And well, we progressed, like you, where, you know, growing up didn't have a computer, started to really computers in a practical use were for me, in university. So we're talking, you know, late 80s, early 90s, and then, all of a sudden, the internet really didn't start to kick in until around 95. Now, what ended up happening? If you think about the time period between 95 and, say, 2010, that 15 years you had the advent of of smartphones, you had apps, you had social media, you had e-commerce. There was a lot of transition that happened there. That was 15 years. Well, it was 20 and 30 year olds mainly that were a large part of writing that the rules of Wild West.

Barry:

What's happening with a lot of 20 and 30 year olds? A lot of them are very concerned about privacy and a lot of other issues, and rightfully so and a lot of younger people are embracing it. So I'm not in any way suggesting that they're not, but the people that are most embracing and I'm finding are actually 40 plus crowd, and what's very interesting is we've got the history, the experience, in whatever capacity that we have, that has allowed us to really tap into AI and get more out of it, because we can bring the strategic thinking and all of our experience and say now I want you to take what I know and build off of it. Here's the problem. We used to rely on junior and intermediate people to do those jobs for us and we would teach them, we would mentor them, we would coach them.

Barry:

Well, over the next five years, the next 10 years, those jobs are basically going to be done by AI. So how are young people going to adapt? Which means everybody needs to understand AI and, I would suggest, need to start implementing it. But younger people in particular need to learn. How are they going to navigate this, knowing that that mentorship, that coaching and a lot of those opportunities are not going to be there? And that's a conversation that we actually have at Autoagentic often in terms of how can we try to help provide solutions and guidance in this area.

MC:

Hey, does your marketing agency suck? Listen before we hop back into this episode. I know you know me as the host of the Dealer Playbook, but did you also know that I'm the CEO of FlexDealer, an agency that's helping dealers capture better quality leads from local SEO and hyper-targeted ads that convert? So if you want to sell more cars and finally have a partner that's in it with you, that doesn't suck, visit flexdealercom. Let's hop back into this episode, Right, suck, visit flexdealercom. Let's hop back into this episode. Right.

MC:

There's a responsibility that comes. It's a responsibility, Isn't that interesting? I also think about this, along with what you're saying. If you know, we went through I don't know how many years, but the majority of the value of a service someone provided was not just on their ability to diagnose that issue but then to fix it. Yeah, I think AI is moving us to a place where all of the value will be in how quickly it can be fixed, because we're not able to mask the diagnosis piece anymore.

MC:

Oh well, I have to hire that plumber, and that plumber is going to charge me for three hours because he's the only one that can diagnose it. Where now I can hold GPT up under my sink with the camera on and say there's a leak and I don't know where it's coming from and it smells weird and there's green moss growing and it's going to take a look and it's going to be like plumber and bypass the thing he typically masked all of his fees in, which is the time and I'm going to say I have a leaky gasket under my sink. I need you to just come and fix it. It just becomes a volume fix thing.

Barry:

Yeah, and that's very true. And I mean, it reminds me back when you had, you know, a very large part of my career was working in agencies. So you walk into the studio and you think about what used to happen when you had physical typesetters and then that switched over to computers and literally typesetters would say computers can't replace what I do. And there was a time and there was a skill, but the value of the skill and the cost in the time wasn't worth it for enough people. So then you had computers that took over and then you had when those graphic design programs started to become more into the masses and people would say, well, can't you just copy, click or make this change, change that to this color, change that to that font? And it used to be that you would have agencies that could craft things. But then time got curtid and you would have thought, okay, well, that gives more time for ideation. That didn't necessarily happen.

Barry:

So to your point, what's going to happen with AI when I can create entire standard operating procedures, implement, do all of these things? And this is part of the great unknown. We don't know. And this is part of the great unknown. We don't know. And this is where are we getting into foe? Are we getting into mistake versus friend?

Barry:

But then you look at it and you try to balance it out and say, all right, but if, instead of concentrating on these mundane things and I'm going to go back to why I think EQ human EQ plus AI is the winning combo, human EQ is not going to get replaced by AI. So is this going to give more time for creating relationships? Is this going to give more time for being able to establish a better and a new relationship that's more real and more honest? So, when you're not worried about having to go through all of these things, does that salesperson now have more time to be interacting with the community? Do they have more time to be checking in on the family? Do they have more time for whatever? It might be and I think this is where the great unknown is really to be decided, but I don't believe that it's going to replace people. I just think we don't know how it's going to influence people and how our society and how we work and how we interact with each other is going to change.

MC:

Oh, this is. I'm just. I don't know if you can tell, but I'm enamored by this conversation because how critical a conversation this is. While everyone is out there talking about look at our fancy new gadget and gizmo and this and that the crux of the issue I felt it's far more deep. It's far more deep. It's far more deep and I felt so unsatisfied by the AI conversation in general until now.

MC:

I feel like this is scratching an itch for me that I haven't been able to put my finger on because it's the responsibility of it. All of the conversations I've had, barry, you're the first one to articulate no, there's a connection here between human EQ and how we leverage, or what we do to leverage, this new and emerging idea to enhance our lives. And the last thing that I think is so important, it almost makes me feel like a good dad for a minute, because my little daughter came to me and she said do you think being a hairdresser would be a good thing? And I said well, your mother's a hairdresser. If you enjoy it, that's fantastic, but also know that the bigger part of mom's job is listening and interacting with people and less about the actual haircut that she gives.

Barry:

That's a great analogy, actually, and I'm going to use that, if you don't mind, down the road, and I will give you absolute credit. But this is the thing People matter, human intelligence matters, human creativity matters, and, yes, it can elevate below average and slightly above average, but that top quartile, regardless of whatever it is, that is something that's unique to humans. And let's go back to your daughter. So Mike Carrick, bill Playford and Carla Conkson are the other co-founders, so I want to make sure that I get them out there. Mike has daughters. What's fantastic is, like all of us, we all interact differently, but, more importantly, we learn differently. Right? He set up ai so that each of his daughters, the ai is set up for how they learn. So the same topic. So now again, picture the advantage. And I'm a big geek.

Barry:

So now let's take a look at different applications in AI that actually do have some comparatives. When it comes down to automotive and I'm gonna use the trades. So let's talk about your plumber. So your plumbers come in and let's say that the plumber's part of a larger crew and the larger crew's got electricians and you've got carpenters, and they are highly skilled, they're highly educated. My entire family other than me. They're all welders and fitters, so I've got a high regard when it comes down to the trades.

Barry:

And if you were to sit down and take a look at the trades, they're going to be able to build a beautiful cabinet or they'll be able to install the right floor, they'll be able to get plumbing, and but are they going to have the same customer service, same communication?

Barry:

You literally can walk and sit down and say to AI okay, mrs Smith, here's where with the cabinets, here's where we are with this. We ran into a problem with that. We're under budget here, over budget there, I need time on this and it literally can write an email. That is going to be the sweetest email ever written. Right, that is going to make Mrs Smith feel like she understands what's happening, she is being, she's got answers to what she needs, yeah, and boom, there you go. So when you start to think about, especially when it comes down to trades, when it comes down to CPG, when it comes down to whether it's hairdressing and other things, ai is really going to elevate and in doing that, it's going to be able to also teach those individuals some key skills that are actually going to be reinforcing and strengthening their EQ side actually going to be reinforcing and strengthening their EQ side.

MC:

This is huge. I mean, you saw me look over at Eamer off camera here, maybe a month ago. He and I were talking and he said you know, eamer? He said Michael AI is going to be able to teach us the way that we learn. So almost a mirror of what you just said.

MC:

You were right, you were 100% right and just the implication of that is such a fascinating thought. I mean I could follow that wormhole. Why? Because I'm doing it for myself. Yeah, sometimes there's. I mean, I don't know, maybe I'm a slow learner, but sometimes I'm like, wait a minute, teach me this again, like I'm six. I've just, I need a refresher on the thing and I like to learn in this way and give me an anecdote or give me an, a way it goes, yeah. In a similar way, the output boy.

MC:

Did I tick some people off on LinkedIn about a month or two ago where I revealed my highest performing LinkedIn posts were written by a GPT that I trained on thousands and thousands of words of how I've written and teaching it, my formula and whatever. Now, what did it do? It elevated me in that it gave me more capacity, but it was still to your point. This is a very simple way that I'm processing. It is that I still had to cross-reference. What an output. I had to cross-reference it. To my heart and my gut Would I say that Is that the position. No Tweak Adjust, but my highest performing posts for a 30 day period were all written by a GPT that I trained. Yeah, and I just can't help but think how fascinating the implications of where we're headed. I love the human element, though. I love that you so distinctly said people matter, period, full stop. And and it's also making me think you better get into sales, because sales ain't going away. It's a people thing it totally is.

Barry:

and when you think about the areas of sales that sales people hate and we're quite frankly so there was a recent so don't panic when I say this but there was a recent survey that indicated and I think it was about 82% of consumers would rather deal with AI and buying a car than a salesperson. But here's the thing and this is why don't panic A lot of it is because the very early parts of that conversation, they're not getting the answers that they need to in the timeframe that they need it. So, where you have AI being able to work in Right, it's now. How can I now start to establish that human connection? And it's when you view it as a team and you think about how many leads got dropped, how many leads weren't followed up correctly, etc.

Barry:

Now, there's a lot of reasons, and part of the reasons too are not everybody's comfortable conversing in those different mediums where AI can adapt to that in nanoseconds. So you know you are going to see that team-based approach, but at the end of the day, people do buy from people, but people are also have very unique needs and you can't guess what's on that person's mind. So, using AI to be able to adapt and then using the people side to that, now connect. That's now where you're going to actually get better. Not only CSI from the customer standpoint, but think about what a better experience that is for the employees now.

MC:

Yeah, I mean, and it feeds the triangle so perfectly. People, inventory marketing, they all feed one another, they're inseparably connected. And just the implication on a dealerships operation. Man, what a fascinating. You've opened my mind here to so many things that I, like I said, I feel like my itch in this AI topic is just being scratched. Now I'm like I'm getting, you know, scratched behind the ear, which, thank you. Thank you for having a deeper well to speak about this, because I think this is exactly where the conversation needs to go. Tell me, as we wind down, how those listening and watching can get in touch with you and connect.

Barry:

First I'd ask visit wwwautoagenticai. My email is barry B-A-R-R-Y at autoagenticai. My email is barry B-A-R-R-Y at autoagenticai, and I'm very happy, one of the things that I will say. I've always been of the attitude of I don't want to sell people. You know, if I have something that you want, then let's have that conversation and it works. But I'm very happy, especially as it relates to tech, to be part of a conversation that's educational and my belief, honestly, is, the more educated, the more aware we are your kids. To me, that's great. So if anybody has any questions, reach out to me. I'm happy to talk. We're constantly doing webinars that are very educational webinars and we also have, on Autoagentic, practical implementations of how you can use AI in your dealership. But we didn't want to make today about selling, but that is one of the areas that I think people could really start to see how they could apply it within their business.

MC:

Amazing, barry. Thanks so much for joining me on the Dealer Playbook. No thanks, it's great to see you again, mike. Yeah, likewise. Hey. Thanks for listening to the Dealer Playbook podcast. If you enjoyed tuning in, please subscribe, share and hit that like button. You can also join us and the DPB community on social media. Check back next week for a new Dealer Playbook episode. Thanks so much for joining.

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