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00:00 – Why Commercial Contractors Need Better Marketing
00:00
Jack Jostes
And sometimes the best foot in the door offer is even simpler than that. To me, the best way to track is how did you hear of us? Your customers feel special and they want to see things that help them feel special. Earlier this month, I hosted a live virtual workshop on winning commercial snow and maintenance contracts. And something happened that I wasn't really expecting. We had real commercial snow contractors from all over the country show up. Rochester, New York, Detroit, Pittsburgh, Long Island, Madison, Wisconsin. And they started talking to each other. And it was fascinating because people were just showing up on this webinar having a great conversation about their wins, their frustrations, who their hell yes customer was, and some of the things that you just don't often get to talk about unless you're with a bunch of other contractors.
00:53
00:53 – Five Lessons From The Commercial Workshop
Jack Jostes
So in this episode, I'm pulling five of the best moments from that workshop and sharing them with you unfiltered, along with some of my own commentary. So we're going to cover why HOAs are a minefield and why that doesn't actually matter if your marketing is specific enough. We're going to talk about gold mining, how my director of client strategy, Robert Fenton, closed a sale at the end of the quarter by digging into the data instead of cold calling. We're also going to talk about one of my favorite things, which is lumpy mail, how to do offline marketing that ties into your digital marketing massage chairs and edible arrangements. How some people I know are sending out edible arrangements, those. Those, you know, fruit arrangements to get commercial clients. And we're also going to talk about AI search.
01:52
Jack Jostes
How does it actually work and what matters for your commercial landscape company in 2026. So if you're new to this show, my name' Jack Justice. I'm the CEO of Ramblin Jackson, and welcome to the Landscapers Guide podcast where we share sales, marketing and leadership inspiration to help you grow your snow and landscape company. Now let's get into some of the clips from my commercial workshop.
02:18
02:18 – The Truth About Working With HOAs
Speaker 2
I mean, right now we're mainly residential. So that's why I said HOA is because we have got a lot of maintenance work that we do for residential work. I'd like to stay in front of them, get those leads in. That's why I'm saying HOA. I'm. I don't want to pigeonhole to that, but that was reasoning behind my comment.
02:37
Jack Jostes
I like it. So, so hoas and how many. Who here hates working with hoas? Anybody want to unmute? Is it R Cuneus? I. I can't see Your first name, Sorry, if you could unmute and tell us why you raised your hand. What's your name? What's your name. And why do you hate hoas?
02:56
Rich
It's just the first to complain when somebody, they should see activity. They're expecting more activity. You know, operating in snowstorms can be pretty dangerous. And they just, if they don't see stuff, especially if they're, you know, if they're on a lump sum thinking that their money's going to waste if they're not seeing the activity. But you know, you can't be out there shoveling during blizzard conditions. And site safety is important, but we understand. And a lot of them start at 2 inch triggers. And you know, on, we're on Long island, sometimes we don't know if it's gonna hit 2 inches, so we gotta prepare for that. And there's a lot of variables. I mean, snow is variable in it and it's in its own sense. But it's just, you got 150, 200 different bosses evaluating your work and bubbling it up.
03:43
Rich
And that hurts your referral network because social media lives on.
03:48
Jack Jostes
Yeah, for sure.
03:49
Speaker 3
You get.
03:49
Jack Jostes
And then the thing about an HOA is that there are potentially hundreds of homeowners in that association, and if things go poorly, you might get dozens of negative reviews. Right? And now you've got all that. So the reason why I asked, I don't have a dog in the HOA fight. Ryan. If you like them, I can help you get them. What was your name again, sir? Arcanius.
04:16
Rich
Sorry, It's Rich.
04:17
Jack Jostes
Rich. Okay, Rich. If you didn't want them, you could design your marketing to say we do not service HOAs. Right?
04:25
Rich
Because a lot of our landscaping customers are HOA, so we kind offer those services to our landscaping customers. So that's, that, that's not a, that's not a good route for me.
04:34
Jack Jostes
Well, so we would talk much more in depth before we made any kind of change. But my point is that both of you consider them commercial. Right? And so if in our marketing we only say that we do commercial marketing, the customer's gonna be like, I don't know, do they actually work with me? I run a, I run an apartment. I don't really care that you can do an HOA. I'm an apartment. I'm special or. Well, I'm a hospital and I have enormous slip and fall liability and I'm special. So your customers feel special and they wanna see things that help them feel special. I love that moment. Because it doesn't mean much to say in your marketing that you do commercial landscaping. You've got to be specific about which types of commercial do you do?
05:26
05:26 – Why Niching Down Wins More Commercial Clients
Jack Jostes
Hoas, hospitals, airports, municipalities, industrial warehouses, retail, strip malls, they all have completely different pain points, different decision makers, different sales cycles, and different liability concerns. So when your website and your outbound marketing speak specific to the pains that a property management of a property manager of one of those property has, they're going to be more likely to actually respond and pay you more. Right. They're going to be more likely to partner with you when they see you as somebody who specializes in what they do versus just a generic commercial company that does everything. So once you know who you're targeting and you've got those leads in the database, how do you close them and how do you know who to follow up with first? That's what Robert Felton, our director of client strategy at Ramblin Jackson, calls gold mining.
06:25 – Gold Mining Your CRM For Sales Opportunities
Jack Jostes
So here's how he explained it at the workshop. Oh, by the way, Robert is our director of client strategy. He's worked with me for nearly nine years. He's talked with, I'd say, over 1,000 snow and landscape company owners. He's really knowledgeable of business. He helps people with their strategy. And one of the things Robert does at Ramblin Jackson and then when he's working with our clients is gold mining. So, Robert, what is gold mining?
06:52
Robert Felton
Yeah, so gold mining is utilizing your sales data to help identify qualified leads or people who are closest to buying. So I mean, an interesting example is we have cookies on our website. I could see when somebody's been to our pricing page. You mean I have client lists. This is a webinar you're at. I can look at webinar attendance and how many. Maybe you've been in a different webinar before. So have you been to two or three webinars? Have I met you at a trade show? So I have this data and information and I mean, I was close to making my quarterly bonus. And I went through the people who are closest to buy and was able to identify someone who saw Jack speak in Mexico, in Utah, and closed him right before the end of the quarter.
07:37
Robert Felton
And I had data information to show that he was on the website, he was actively attending events, and when I messaged him, he knew who I was, he knew Jack's name and was able to have that conversation quicker. So it's about not treating every lead equally. It's about having that data and information. Looking through your sales data, are they opening your emails? Are they clicking on Jack's podcast? Consistently? So this is information that's available to you that you should be monitoring because you gotta know who is the closest to closing and who's an A lead, who's a B lead, and who's a C lead. And if you use this information correctly, you can usually see who.
08:13
Robert Felton
Who is having an issue with their service and is on your website, who is opening your emails, who is looking at your download, who downloaded your checklist, your toolbox, different things like this. So it's utilizing that sales data to make educated decisions to maximize your time and spend time with the people closest.
08:32
Jack Jostes
Now, what Robert just described is the difference between winging it and having a system. He didn't cold call a stranger. He found somebody that had already seen me speak, who had been to multiple of my workshops and had been on our website. And he had a warm prospect who just hadn't been contacted yet. But here's the thing. Gold mining works on the digital side. And what about the physical side? In my book, coming up, the Landscapers Guide to Direct Response Sales and Marketing, I advocate for both offline print in person and online marketing, because when you do both, you get the best results. And this is where outbound marketing can get really creative. So in this next clip, I'm going to show something that's worked for years. It's. It's lumpy mail.
09:26
09:26 – Lumpy Mail That Gets Commercial Buyers' Attention
Jack Jostes
So I told a story about a landscape company that used a mobile massage chair to get their biggest commercial account. So lumpy mail is sending mail that's beyond just a little postcard. I love postcards. They have their place, but mail that's lumpy. And then having some sort of experience like this mobile massage chair is what actually stands out. Who typed the word tree in the chat? We're going to send you a toolbox in the mail. We're going to literally ship you some beef jerky, and that is called a lumpy mail. So this is a. We've spent quite a bit of time on the digital side. One of the other strategies is using print mail. So if I were you, I would think of a way to send lumpy mail. So what is lumpy mail? Let me show you something.
10:20
Jack Jostes
Just organized my office, you guys. I get behind sometimes, but it is organized right now. So here is some lumpy mail. It's kind of a hideous gold package. I bought hundreds of these on Amazon years ago. And we've, we've just had an amazing result because if you get this in the mail, right, it's lumpy, like it makes you curious what's in here. Whereas if I get, oh, something like this, it looks like a bill or something. This, this probably was a bill. It's in my shred pile, right? So sending the lumpy mail creates curiosity. Now, what's in here in this case? These are actually just straps that go onto our trade show booth. So this is, this actually is an example of what I'd send to a client. But maybe I'd send them beef jerky. Maybe I would send them something interesting.
11:16
Jack Jostes
I wrote a, a LinkedIn post recently. I have a client who their offer, their foot in the door offer was, hey, you know, we know that you in your office, you work really hard. What we found is some of our clients enjoy when we have a, a mobile massage studio come in and they do chair massages in the break room or whatever. And the clients, they were like, yeah, our staff would love that. And they did. So that was unusual. Maybe you need to do a lunch and learn. You got to have a foot in the door offer. And then when they get it from you, what are they going to do? Are they not going to Google you or are they going to Google you? What do you think, Thomas? Are they going to Google you?
12:00
Thomas
Most of them do. I try not to put anything till they get by name and then they find us by going look for us because we've had that first contact, building the relationship.
12:09
Jack Jostes
Yeah, so my point is this is where like marketing would support outbound sales. Marketing supports outbound sales. That's the whole equation. A lot of companies see marketing over here and sales over there. And if you look at my titles, if you look at of my webinars and in my book and all these things, sales and marketing should be done together because the goal is sales. Right? Marketing is here to support sales. And when people google you, if you're doing outbound marketing or cold calling, that's a salesperson. Outreaching marketing needs to back them up. It needs to support them. Your case studies there, if you have a hospital page on your site, if you have testimonials from hospitals, if you're targeting hospitals. And sometimes the best foot in the door offer is even simpler than that.
13:02
13:02
13:02 – The Cold Call That Landed A Six-Figure Account
Jack Jostes
And we had Rich from Brightview on Long island share a story that sometimes the best tactic is simply showing up.
13:11
Rich
I was just kind of helping out, you know, some Things that you could do, get your boots on the ground, knock on doors, whatever from retail. Big box. Hey, what do you. I mean, I had one of my largest clients, Wegmans, I. I went into. They weren't even on site yet. I just went in there and talked to one of the store managers for a DSW and I was like, who's the property manager? And they just handed it over and I called them and the rest is history. You just kind of build rapport, asked pointed questions and figure that out.
13:40
Jack Jostes
Yeah. Well, I love it.
13:42
Robert Felton
Yeah.
13:43
Jack Jostes
So I love that Wegmans wasn't even open yet and he walked into the DSW next door, asked a stranger who the property manager was, and that turned into one of his largest accounts, that boots on the ground, outbound sales. And it still works. So here's a question that came up near the end of the workshop and I think it's on every commercial land, every business owner's mind right now. What about AI search? How do I. How do you show up when a property manager types a question into chat, GPT or Gemini? I answered this live and want to share my response with you. Let's talk about AI search. And so I created.
14:26
14:26 – How AI Search Is Changing Landscape Marketing
Jack Jostes
I'm creating this new book, I'm releasing it, and the way AI works is really that it extracts data from a variety of sources and then serves it up into whatever AI tool you're using. So that could be Google's AI overview. Google's AI overview is actually the most used AI tool. It is still the predominantly used search. It includes things like ChatGPT, it includes things like Gemini. And Gemini is Google's tool and it's built into everything. Like if you use Google anything, you're using Gemini and Claude. And so a lot of the ways to show up in AI are very similar to how local SEO works. Having the content on your website. And this is again where having the specific content on your website, because the prompt might be different. It might be. I'm the property manager of a Costco in Menominee Falls.
15:30
Jack Jostes
I need to get three estimates from commercial landscape companies for snow removal. My last company was dropping the ball. Help me find three companies, right? And so what's AI going to do? It's going to extract data from somewhere on the Internet, looking for those words about commercial and Costco and things like that. So having that content on your website is the most important thing. The websites are the most cited sources in AI. The other thing that's really changing is the importance of reviews. Having reviews not only on Google but also on your website with first party reviews. And then social media is enormously important. Now social media shows up as a source in AI as far as tracking the result from it. What we've founded, the best way is to have a form that asks how did you hear of us?
16:26
Jack Jostes
And so that's where in lead wrangler for our clients, we're then able to, if we go back to. Let's see here and Robert, do we have a demo sales and marketing dashboard? You know, we can see the marketing source. So the client could say I found you on Google Search or the client could say I found you on AI search and we build a form on the website that's an internal form. So let's pretend it's a phone call. By the way, how did you hear of us? Oh, I was using Chat GPT and it was amazing. It showed me you great. I would then check the box on that and it goes into my CRM. At this time in July 2026, I haven't found a very reliable AI visibility tool. There are many tools out there that allege to report on your AI visibility.
17:20
17:20
17:20 – Measuring AI Marketing Results
Jack Jostes
But there was recently a study that there's a 1 in 1,000 chance that the same prompt will deliver the same result to people. And one of the reasons for this is called personalization. So if you're using ChatGPT or Gemini or Claude or Copilot or whatever, like it starts to know you. And if you're using Gemini, which is about to surpass Chat GPT, it uses everything in your Gmail. And if you use YouTube, if you're logged into YouTube. Right. So Thomas might enter one prompt and Elijah might enter the same prompt. But because of everything they've done online up until that point, they're going to get a different result. So I don't think it's super trackable. Like SEO has been very trackable. How do I rank for this keyword is pretty trackable.
18:17
Jack Jostes
So I'm curious if whoever asked that if that was helpful and the takeaway really is that you've got to focus on being a source of data online from which AI extracts and then ask to me the best way to track is how did you hear of us?
18:34
Thomas
Yeah, Jack, I think that's important. We're just noticing the amount of spend on Google Ads versus hey, we have client attribution that we're actually dropping into ChatGPT or Gemini and how do we account for that and how do we populate that the definition on the back end was helpful.
18:53
Jack Jostes
Yeah, I one question, Thomas, is on your contact form, do you have AI as an option for how did you hear of us? Do you know?
19:03
Thomas
Yes, I actually I have ChatGPT, Gemini and Copilot.
19:10
Jack Jostes
So you have specific options. Are you seeing a trend right now? Chat GPT that makes sense. I, I, I say that it has the Kleenex effect in the sense that everyone knows if you're going to use tissue, it's probably a Kleenex.
19:25
Speaker 2
Right?
19:26
19:26 – Final Takeaways For Winning Commercial Contracts
Jack Jostes
Most, most people are using ChatGPT generally. So there you have it. A few of the key highlights from our how to win commercial snow and landscape maintenance contracts. And the key is to get specific which type of commercial clients do you actually work with? When we're designing marketing systems for our clients, we get really clear on who do you work with and we build the marketing behind that because the hospital wants something different from the retail shopping center and from the HOA and they don't care that you've done a municipality and so on. Everyone wants to feel special. So make them feel special, build that content, approach them differently. And I'd love to see you at one of our upcoming events. We've got a variety of in person and virtual events. My name's Jack Justice.
20:17
Jack Jostes
Join me at one of them landscapersguide.com/events and see our show notes for a link. And I look forward to talking to you next week on the Landscapers Guide.