Search Interviews:

Jeremy Weisz  14:13 

You know, I mean, what I want to talk about, too, is you mentioned, the customer journey. Right? And I want to tell your customer journey, too. But let’s talk about so we’re looking at a website here. And because a website is just, you’re taking them through a customer journey, like you said, and you mentioned that. So what are you thinking about with the customer journey when you’re creating a website like this?

Kyle Orlando  14:43 

Yeah, I think the best place you can draw from is your own experiences as a consumer. You only get to go through it typically most people, three, four or five years depending on how often you replace your vehicle. And I just recently got to do it. My wife needed a new vehicle. And we got to do it a few months ago. And it’s just the best experience as somebody who works and lives in this industry. It’s really hard to separate what you know, from actually being in the consumer’s shoes. So I got to do that again recently. It’s always my favorite thing to do. But yeah, as far as the customer journey itself, I just look at what I would want. As a consumer myself, that’s always been our focus. So, big images, quick navigation, when it came to new vehicles, that was something that we spent a lot of time on. You’ll notice on our sites, they all specifically say new vehicles. That’s because we have an inventory section, we have a built-in price section, we have a showroom section, with the ability to compare trim options. I remember something that stuck with me, my aunt, the wife of the uncle, who originally founded EDealer. I remember she lives in Sudbury, where it’s very often in the winter minus 40 degrees. And she said, I will never buy another vehicle that does not have a heated steering wheel. That was her principal. So she didn’t care about leather and all the other things. She needed a heating steering wheel.

Jeremy Weisz  16:04 

It was funny you say that because when I got my last car, I’m like, who the heck needs a heating steering wheel? Why do I need a heating steering? I mean, I’m in Chicago, too. So it’s cold here. But I’m like, that’s a thing. So yeah, There’s a place colder than Chicago Kyle. Okay. Yeah, there’s a place colder than Chicago.

Kyle Orlando  16:23 

Exactly, there’s certainly is, there certainly is. That’s what she wanted. So, we designed our build and price two on a way that as you’re going through your trim selections, you can see side by side, each trim and package and what options come with that. And so it was really important for me that when we were building out the building price that we did that we actually just rebuilt it, we’re about to release our new version in the next quarter or so. And it was important that we retain that to me, because I think when you’re going through and building a vehicle, you want to know, I asked myself, why is this one 23 grand? And why is this one 27 grand? There’s a reason we know there’s a reason what are the reasons, all the reasons are listed out below. So that was the main thing on a new vehicle side and the US vehicle side for the customer journey. It’s really just the completeness of information. What are the two things you care about when you’re buying a used car, the price and the mileage and the CARFAX report will say that too, but the price and the mileage so it’s important to me that anywhere that use car shows up on a website price of minds are really right next to each other big images easy to navigate. So I know that a lot of the concepts that I’m talking about right here are pretty simplistic, I think. But I think they need to be simple. They need to start in a simple place. If you start overcomplicating it, that’s when you really start to get yourself into trouble and creating like the joke I told earlier about the website with nine different paths to conversion.

Jeremy Weisz  16:28 

Let’s talk about your website because I know you’ve gotten this, you guys specialize in this for dealerships, right. But you eat your own dog food as well. So talk about your website and why some of these elements are the way they are here.

Kyle Orlando  18:02 

Well, I will start off by saying we’re in the process of a rebuild right now. And it is the carpenter’s house. So that’s how I feel about it.

Jeremy Weisz  18:15 

But we see some things like right here at the top, there’s a specific clear headline you have you want people to do certain things here, just walk me through the thought process.

Kyle Orlando  18:26 

Yeah, well, you’ll notice our requested demos highlighted and our latest innovations isn’t why because that’s ultimately where I’m trying to drive the user. There was some, one of the retailers that I borrowed a lot of information from early on with Zappos. Zappos is known for having a great online experience. They’re known for having great customer service. That was a company that I admired from when they first started, and I was in college and I ordered shoes from them. So I looked at what Zappos did, I looked at what Amazon did with two major successful retailers and looked at how they set up their calls to action. How do you drive people down the path to conversion, and it’s really just giving them that green light of consistency throughout the website. So that there is contrast between something that is a tool or a feature that you’re going to do research on, or a button that’s going to take you down a path that conversion, I would say that’s kind of rule one A for me, is making sure that when you’re on a website, the website is clearly telling you to go down one of these two paths. Either path is fine. I think we all know anybody who has a website, you want them down that path to conversion, but not everybody’s going to click that request a demo right off the homepage, right? You need to take them down into those research sections. So yeah, I’d say that’s the overall philosophy and then you can see it applied throughout this website as well as our dealer websites as well.

Jeremy Weisz  19:44 

I mean, the other thing I see here, there’s a video right, obviously, that people can click on source information. You also have some social proof elements here with the different, we see Toyota Lexus for GM, here and also this chat. Yeah. Right. So talk about, I mean, I’ve had a lot of people kind of, I don’t know, struggle is the right word, but like, should we put a chat on there? Because now we have to woman or man the chat, right. And so the decision to put a chat on there is not an easy decision to make either.

Kyle Orlando  20:19 

Yeah, it’s funny that you bring that up. It’s actually a great example of sort of how I approach our company and so forth. It’s not showing my picture right now. But I am signed in right now. So a few months ago, one of our large dealer groups from out west had been with us for years, was messaging through the chat for support issue, and I answered it and reached out like, is this actually Kyle or somebody pretending to be Kyle? And I was like, No, this is Kyle. He’s like, I’ll never get over the fact that you’re the president, that company and you’re still answering chats on the website, when we talk to our customers that are running a very different business than us the car dealerships, right. So it is very difficult for them to man those chats and answer those chats. My guidance has always been is, hey, you got to treat it just like a phone call. It’s just as important. But I understand that they’re facing different challenges than we are. On this drift chat, which is a third party tool that we subscribe to, myself and four or five other people are all signed into it on their cell phones right now. So when somebody starts to chat, it will immediately flag and I get a notification from the app on my phone. And wherever applicable, we can start talking with the customer or whomever it is. So that tool has been on our site now for probably five or six years. And we love it. It’s been fantastic. And I like having that insight I like that my phone gets lit up with the commentary. And I like to see what’s going on and what people are asking about even though I might only be answering 10% of the chats.

Jeremy Weisz  21:49 

Yeah, you kind of allows you to have your finger on the pulse. What else? Kyle, from a tech stack perspective that you like, it could be apps on your phone that you use personally or business, but so use drift. What are some other things that you use as a company or that you find productivity wise, personally?

Kyle Orlando  22:09 

Yeah, I mean, Slack is one that obviously I think most tech companies, a lot of companies now are using, adopting slack and the different groups and ways that you can set it up to be more efficient. So you’re only getting the communication you really need. We did a major migration from the Microsoft stack over to the Google workspace in the last two years, which I was extremely resistant to. I was just resistant to change. I’ve been on the Microsoft stack for, I don’t know, 15 years, whatever. And I have absolutely loved it. As far as like…

Jeremy Weisz  22:45 

What prompted the change, right? Because like the changes I’m like, that is a big decision is a big implementation. It’s an annoyance, like, I could see why you would resist something like that.

Kyle Orlando  22:57 

Yeah, well, because our company was growing so rapidly, I want to say our company E INC itself. And we just wanted to get everybody on the same stack. Some people were using Google workspace, some people were using exchange. And it just made sense from a technology standpoint, it just made sense. We’re all using Google Sheets, we’re all using Google Meet. And it just made sense. So it’s funny I’ve watched over the last year. So just the way we started eliminating other pieces of technology, go to meeting, for example, things of that nature, Zoom, and just using the full Google Suite. And I will say the early days when I was using let’s say, three, four years ago, when Google Meet was still not predominant. I had a lot of technology issues with it, like a lot of connection issues, just problems with it. But I will say it’s been a fantastic experience over the last year. So using that, I would say the one specific thing that was a huge draw for me is the calendar functionality to be able to see people’s availability that’s saved so much time where we just didn’t have that before.

Jeremy Weisz  24:02 

I love to talk about the trajectory of your journey. Because it’s not often that I hear oh, “this person started as washing cars, now he’s president” type of thing. What were some and what are some of the positions that you held throughout your journey and maybe something you learned that that brought you to, gives you a better viewpoint as president, because I know you started, you did support you did project management, you did strategy, you did all these things. Maybe just take me through the timeline of the position. And then one thing that you took out of it?

Kyle Orlando  24:39 

Yeah, sure. And so as I mentioned, you know, this company EDealer was born out of that small 30-car lot where I was just a lot boy basically doing anything that needed to be done from delivering cars for hours to Toronto, or washing a car or putting on a snowmobile suit in minus 40 and blowing all the snow off the cars. From there, I came back in 2009 and started off as customer support. At that time, our entire customer support team was located in India, we had six or seven support reps there, we had, I believe, four develop web developers. And so I was sort of managing that team and running customer support myself. And that’s when I first started to recognize the inefficiencies of having an offshore team, there was certainly savings that we needed as a small startup, to leverage those offshore resources. But I was seeing kind of the give-take in that. And so as we went through that, I started really just trying to focus on quality over quantity. And when I moved into the project manager position, out of the customer support and customer support management role, I really started to see it, I really started to see what we were losing offshore. And again, we are talking 13 years ago. So it could have changed or could have been just my experience, I just want to outline that. But communication issues, timing issues, just overall quality issues. And so while I was in project management, I put together a business plan to move us onshore. And so when we kind of never looked back.

Jeremy Weisz  26:25 

Was that something that you initiated or someone higher up was like, hey, we want to move this onshore, that’s something you were like, I think this will improve the company. So you were bringing new fresh ideas, essentially.

Kyle Orlando  26:39 

Yeah, at that point, I had already had the experience in our Customer Support Department, I have the experience now in project management, that’s two of the main parts of the customer journey, that’s where you’re interacting with the customer. That’s where your key deliverables. And so it was clear as day to me, and so it was really like, well, here’s the budget, figure out how to get it done. And that’s what I did. And so we didn’t do it, definitely wasn’t a band-aid poll, we did it slowly and methodically. And we did have to go from four resources down to two in certain areas. But what I found was, it wasn’t just that the productivity or the quality of the individuals was better, but the communication was so much better and cleaner and streamlined, that the productivity went up. Does that make sense?

Jeremy Weisz  27:25 

Yeah. So customer support, then project management. And then you brought this, to bring it on shore, what was next?

Kyle Orlando  27:34 

From there is when I started, I moved into sort of my marketing and product role. And so that’s kind of a weird mix, looking back at it now. But I had the marketing background, we weren’t doing a lot of specific marketing, we were doing marketing for clients, but not marketing for ourselves. So I started focusing on that, and then just finding ways to improve the product. So a lot of stuff in the philosophies I just talked about earlier was we were talking through our philosophies of setting up a vehicle details page, or a listing page or the homepage, working with our CTO at the time to give them that feedback and tell them exactly what we need in our next iteration was some of my main focuses there. But that’s also when I started dipping my toe into the sales waters, at that time, we had a third party, that was kind of our sales arm. So we paid them to do all of our sales. That’s what they did, they did an excellent job, they opened tons of doors for us. But it was expensive, it was expensive to outsource your sales for so I started dipping my toe in there. And that’s when, shortly after, there’s kind of three things going on there. So I’m involved in product, I’m involved in marketing, I’m involved in sales. And we figured out that we can make a lot more investment in the company and in the product. And the ops folks, if we brought the sales in-house, so we moved, Shane Hambly, who’s been with the company, he’s with the company a year longer than me, he’s still with us, as our VP of real estate at the E Ink level. We brought him out of that organization over to us and he and I just led sales, just the two of us from then forward for until I think 2018. And I learned a tremendous amount from him about how to sell how to present yourself. I learned a lot in those few years, kind of he took me under his wing on the sales side. And that’s really how I got interested in the sales side of the company.

Jeremy Weisz  29:29 

Talk about that for a second. So what were some of the advice he gave on when you say how to present yourself or just on sales in general?

Kyle Orlando  29:37 

Well, for one, he got me dressing better because I wasn’t in the office anymore. I was going out to visit with clients. But it was just the way he held himself. You know, I mentioned earlier about the diversity of the leadership that I saw on my way up and he’s one of those leaders and our sales styles couldn’t be any more different. Anybody who knows us would tell you that our sales styles today are very, very different. But for me to learn those things I would say everything he’s strong at were some of my weaknesses. Like he can stand in front of a boardroom of 20, quiet people and just present and absolutely kill it. That’s not my style. This is my style. Having a conversation with somebody, having a conversation with a group of people is absolutely my style. So his presence, his ability to prepare for a meeting, be prepared for anything. Those were some of the things that I took away. And it just really gave me the foundation for me to create my own style and understand that I can go into a meeting confidently and close.

Jeremy Weisz  30:39 

What were some of the things that you had to do to bring the sales in-house or that you learn from that outsourced sales team? Like let’s say someone’s in a similar position to you like, yeah, we’ve been outsourcing sales, or we want to just be better at sales. What did you learn from the outsourced sales that you brought?

Kyle Orlando  30:59 

The number one thing I learned in SaaS, which has been my experience, is more salespeople does not equal more sales. That’s number one. Quality over quantity. As I mentioned earlier, we were competing with companies with bigger war chests than US companies that are bundling, for example, like, I’ll give you an example auto trader who has a marketplace that makes tons of money off of that marketplace, and then bundles that with websites, and has a ton of reps on the road. Meanwhile, I have for, back then we had to, it’s really about the quality of those interactions. And that’s not taking anything away from that third-party company that helped us grow in those early days, because they were fantastic. But what they were really doing was just opening doors, and then Shane was going in and closing the door. Right? So that’s what we learned was just that kind…

Jeremy Weisz  31:47 

At that point of acting is like a sales development rep than they were kind of getting in the door. But then ultimately, you still had to do the sales, like do the final closing of any deal.

Kyle Orlando  32:01 

Exactly. And I think once my uncle was still running the company at that time, Chris Whitehead was still running the company at that time. And he saw me dipping my toe into the sails and that I was having some early success and said, well, now we’ve got two people that can do this, I think we can do this. And then we went over the raw numbers and just said, we’re giving away 40% of the top line right now to this third party sales. We can take that, we can invest onshore, we can rebuild our product, we could just take that money and use it in so many other effective ways.

Jeremy Weisz  32:34 

I’m curious, Kyle, about the project management side of things. So you go from customers poor to project management, a strategist to marketing and product development, and then eventually on the president, but backing up to the project manager, each time you had to kind of replace yourself in that position? That’s right. So from the project management piece, what were you looking for? What do you look for in someone that is a really good project manager, right? Because it’s not like when you studied in school, right? You were like, I’m gonna be a, you were studying specific, or you didn’t have a certification project manager? I mean, you did marketing in school. So what did you find of the, actually, the qualities and characteristics of someone who is a good project management replacement for you?

Kyle Orlando  33:29 

Yeah, I mean, you have to be an excellent communicator. Number one, you have to be confident and you have to be organized. I mean, those are the key tenants that I see in that role. The confidence part I would not underrate like, it’s so important when you’re having these conversations with people about their websites I go back to when I was watching that previous podcast with John on it. And he talked about it as well as setting up those guardrails and making sure that the customer feels heard and making sure that all those things are happening. If you don’t have confidence going into that and you don’t have a good plan in place, and you don’t have your milestone set and all those things. You either have it or you don’t like it’s really been my experience. So we’ve had some people that we brought into the company, to work in that position that have been really great people, I’ve actually moved them into other areas of the company. But I do see that role as a very specific skill set in a specific role. That’s that I do believe that many, many people are capable of being successful at it. It’s also the wherewithal of wanting to do it. I think a lot of people that could be good at it end up in sales where maybe they have some more upside opportunity for income, right. So it is an interesting role. It’s one of my favorite roles, if not my favorite role on the way up. And it was very difficult that you said I had to replace myself each step of the way. And I learned a lot in that we just recently had somebody that didn’t make it past her probation period. And I had a follow-up meeting with the managers that were involved in the hiring. And ultimately, the letting go of the employee and I sat down with them and I said, What did you learn? What did you learn from the interview process to the onboarding to now the off-boarding? What did you learn? And they did learn that you got to, I’ve heard the term before, fire fast, hire slow, which I think really absolutely applies here. And I said, look, guys, you know, I’ve been duped by people that are really good interviewers before. So don’t be embarrassed, it’s happened to us all, you work long enough, as a manager or leader in any industry, you’re going to be do so don’t feel bad about it, just understand how to identify and move past it as quickly as possible, because you’re only hurting yourself by trying to what I call managing competence. There’s nothing that bothers me more than managers who think they can manage that there’s such good managers that they can manage their way through incompetence, and I mean, incompetence and the true meaning of the word.

Jeremy Weisz  35:57 

First of all, I want to thank you one last question. Before we end, I want to just point people to check out to learn more and more episodes of the podcast. But my last question kind of goes along the, you’ve kept going into increasing roles and responsibilities. What does your role look like as president now?

Kyle Orlando  36:22 

Yeah. It’s been interesting, because I’ve liked everything I’ve done along the way, I’ve been in this role. Now, I was surprised I looked it up the other day, because I couldn’t remember what it was, but six years now. And I find myself removed from the day-to-day of the business more and more, which I don’t like. So I find ways to keep myself engaged, like the chat that we talked about earlier, or just with my leadership team. I’ve learned a ton in the last three years, I’d say since we really hit a growth spurt since our company IPO and just being responsible for a p&l and all those things. So it’s funny because I was one class away from a minor in finance in college. And I didn’t take that class, because I did not like finance, and the amount of time that I’ve had to spend in spreadsheets and in financials, but it’s been for the betterment. So I mean, it looks very different than what this role looked like when I first began. It’s very different. But I think that it’s given me a tremendous amount of experience as I go forward in my career, and I wouldn’t trade it for anything, but it has brought its own challenges. I mean, there are days that I get out of bed and say, oh, why did I ever stop just doing sales? That was so much fun. But I was talking to my director of sales the other day, and she said to me, oh, why ever stop doing support? What’s that? The grass is always greener. Yeah, exactly. So, but like I said, I wouldn’t trade any of it for anything. It’s been an excellent experience. I’ve learned a lot from my CEO, Jason McClanahan, who’s been so supportive because he comes from a different side of the business, he gets transactional, it’s auctions it’s very different from my business, and he’s been very supportive as a leader, but also given me so much room to run my part of the business which I am so appreciative of.

Jeremy Weisz  38:13 

Kyle, I want to thank you, everyone check out And more episodes of the show. Thanks, Kyle. Thanks, everyone.

Kyle Orlando  38:21 

Thanks so much, Jeremy.