Why Rejection Is Unavoidable In Premium Landscape Sales with Chris James
Selling premium landscape services means hearing “no” more often—and waiting longer for the right “yes.” In this episode of The Landscaper’s Guide Podcast, Jack Jostes sits down with Chris James of Perfect Cut Landscaping to talk candidly about rejection, long HOA sales cycles, and how top sales professionals stay confident through it all.
Chris shares real-world lessons from selling residential, commercial, and HOA landscape services in South Florida, including how to follow up without damaging relationships, why professionalism pays off months or years later, and how mindset, systems, and communication separate average sales reps from top performers. They also cover how AI, KPIs, and industry events are helping sales pros buy back time and close higher-quality work.
You’ll Learn:
- How top landscape sales pros handle rejection without losing confidence
- Why long HOA sales cycles are an advantage when handled correctly
- How professional follow-up leads to premium work later
- Practical ways AI can save time in estimating and communication
- How sharing KPIs helps align crews and leadership
Connect With Today’s Guest
🌳 Perfect Cut Landscaping: https://561lawn.com/
📸 @perfectcutlandscaping
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Transcript
00:00
Chris James
Some people are totally happy with the mundane lifestyle and they get a sense of security from that. That's not true for me. You just gotta kind of be a goldfish in this industry and forget about it and move on really quickly, you know, and the more opportunities that I am working on at one time, the easier it is. Every time we come to one of these, we meet great people, we hear those little nuggets, and I go back just like, with a new sense of energy and excitement.
Chris James Returns To The Podcast
00:28
Jack Jostes
Hey, everyone. Right now I've got a repeat guest, Chris James from Perfect Cut Landscaping in Boynton Beach.
00:35
Chris James
Did I say it right?
00:36
Jack Jostes
I always struggle with that.
00:36
Chris James
Now you nailed Boyton.
00:38
Jack Jostes
Boynton Beach, Boynton Beach, Florida.
00:40
Chris James
Yeah.
00:41
Jack Jostes
And it's cool to connect with you here at NALP's Elevate show because we met here two years ago.
00:47
Chris James
Yeah, two years.
00:47
Jack Jostes
The ship. But the show was in Grapevine, Texas.
00:50
Chris James
Dallas.
00:51
Jack Jostes
Okay, well, it's Grapevine. It was technically in Grapevine. It's just outside of Dallas.
00:57
Chris James
Roger that. I stand corrected.
00:57
Jack Jostes
Okay. But anyways, yeah, Dallas, Texas. And you were pretty new to Perfect Cut, and it's cool. Connect. Just wanted to talk to you about what. What are you up to in the green industry now?
Leaving Cubicle Sales And Returning To The Green Industry
01:09
Chris James
Yeah, I appreciate that. Honestly, I. When we first met in. In Grapevine, Texas, I. I had three years experience doing the fertilization and pest control for a different company. I took a. A long hiatus from the green industry. You know, long story short, found my way back and I was. I had been given this opportunity and I utilized the podcast a lot to kind of get back up to speed. And I was just trying to consume information any opportunity that I could. So there was, you know, still to this day, but. But even more so then, like, I eliminated music from my life, and I was only listening to podcasts and other forms of educational media to kind of get going as fast as I possibly could back in this industry.
01:56
Chris James
So it is really cool that we're hanging out two years later and that we work together now.
Why Landscape Sales Offers Variety And Fulfillment
02:01
Jack Jostes
I agree. So you worked in the green industry, and then what did you do in between? You did something else?
02:07
Chris James
I did. I did a slew of different sales jobs. I sold roofs, I sold some health care, and basically ended up in just banging phones where I was in a cubicle, I was tied to a headset, and I was doing that 40 to 50 hours a week. And that's what brought me back to the green industry because I couldn't take it anymore. I needed to be on the move. I needed to be on the go now I'm able to run sales, but I'm running consults. I'm going to do job site visits. There's no monotony to it. Every day is a little different. I get to do a, a ton of cool, fun things in between sitting down and cranking out proposals and stuff like that. So that's what I love about it.
02:48
Jack Jostes
That sounds really fun.
02:50
Chris James
It is, it is. It's a ton of fun. I mean, obviously, I mean it's hard work and. Yeah.
02:54
Jack Jostes
And you know, you're working on. But, but that does sound like variety in the day and you're meeting different people and you're estimating things and you're making proposals.
03:07
Chris James
Yeah, it's a lot of fun. And then there's some instant gratification to it. Like I get to have this consultation with a client. We start to come up with ideas together and I get an idea of what they want and then I get to see that all the way through to our crew. Making it happen and showing up and doing a little quality control and doing a final walk through with the customer and then I get to start the process all over again. So I, I love it.
Who Thrives In Landscape And HOA Sales Roles
03:35
Jack Jostes
I'm realizing as we talk that this is kind of like an advertisement for the green industry in some ways. It's kind of like a career path conversation about doing sales in the industry.
03:47
Chris James
Yeah. If you're working at a position right now and you're in a cubicle, quit your job immediately and just totally refocus your life on the green industry.
03:57
Jack Jostes
Well, who actually should do that?
03:59
Chris James
I think anybody.
04:00
Jack Jostes
Who do you think would be a good fit for that?
04:02
Chris James
Anybody who's like me, you know, I mean, kind of high energy, you know, needs a little bit of variety. You know, some people are totally happy with the mundane lifestyle and they get a sense of security from that. That's, that's not true for me. You know, I need something a little different. I need something to continue to pique my interest and kind of grab me and pull me towards something new. And, and that's how I operate the best when I maintain interests and I'm still having a good time.
Long HOA Sales Cycles And Delayed Wins
04:33
Jack Jostes
What are some of the things you've learned since coming back into this position in primarily residential. But you guys also do commercial landscape sales and you also sell tree service too, right?
04:47
Chris James
Yep.
04:48
Jack Jostes
So you're selling tree, you're selling lawn care, you're selling landscape construction, installation, maintenance, correct?
04:56
Chris James
Yeah. And then kind of cross sell a little bit into the other two businesses that the Snowman zone, which is snowman construction and east coast sprayers, fertilization and pest control. So, I mean, we could do a whole 10 hour podcast on what I've learned in the two years. You know, I've learned a ton. Just about.
05:20
Jack Jostes
Just.
05:21
Chris James
Just about people in general. You know, I mean, I think that especially on the HOA side of things, it's. It's a lot of patience and it's a long sale. You know, sometimes I have sold HOA accounts that I got an opportunity to bid a year and a half ago, and now they finally come around.
Following Up After Rejection Without Burning Bridges
05:39
Jack Jostes
Tell me more about that and what happened in between that maybe got you back into selling to them.
05:44
Chris James
Yeah, so the best thing that can happen to us is we pride ourselves on, you know, delivering a high level of service, a high level of communication, and we charge a premium for that. So a lot of times the community will decide that they're not willing to pay a premium. They'll go with a, you know, somebody who's a lot more cost effective, and then they'll get that kind of experience. And then after, you know, after they experience what less money gets you is usually when we get the call back and they're like, hey, we see the value in what you're offering now. We're ready to up the budget and give you guys a shot.
06:18
Jack Jostes
Well, one of the things that we're working on together now is follow up over time. So we're doing lead generation through organic search primarily. You guys are also doing some outbound marketing. And I like that you mentioned that the HOA sales sometimes take a year, because sometimes my sales take a year or two years or three years. And I'm always trying to follow up with people without being annoying. But being helpful and staying organized is kind of the hard part.
06:48
Chris James
That's. And that's the key is maintain that mentality that, like, I'm just calling to be helpful because it's really easy when somebody, you know, quote, unquote, wastes three weeks of your time that you're bidding. This following up, showing up to HOA meetings to present to the board all the stuff that you put into that sale and then they go in a different direction. It's really easy to be like, you know, bitter or not continue to treat them with respect. You know, it's. That's like kind of your first thought. But if you maintain that level of professionalism and kind of just leave it at like, hey, I really appreciate this. The fact that you gave us an opportunity in the first place, we're not going anywhere. You know, if you have any questions, need any help with anything moving forward, we're always here.
Staying Confident After Losing Big Bids
07:31
Chris James
And who knows, they might call us because whoever they went with is not offering tree trimming or they're not offering fert and pest or they need us for a different service. And then we get an opportunity to come in there and show them what we can do and how we operate.
07:45
Jack Jostes
Right? Yeah. I love that you're ending on good terms with that and being helpful because a lot of times they're getting a lower price bid because it's missing something key and something that seems obvious to you, they end up realizing is missing altogether.
08:01
Chris James
They have a, you know, these property managers, a lot of them don't. They don't only manage one property. So the opportunity, they'll call you and say, hey, you know, I got a nicer community with a much bigger budget that is looking for that level of perfection or, you know, that higher quality of service and they're willing to pay the premium for it. Can you bid this property for me? Or, you know, give us a tree trimming bid. And the, the opportunity might not come right that moment, but most of these people are, they're in it. They're career property managers and they're going to have other opportunities for you moving forward.
Being A Goldfish In Sales And Moving Forward
08:36
Jack Jostes
What are, what are some of the things that you do to maintain your confidence and like, not be crushed by all the rejection? Right. Because business, I think there's a lot of hearing no. And yeah, you're putting weeks, you're putting hours, you're spending time, you're driving around, you feel like you've got a relationship with somebody and then they don't work with you. Like, how do you, what are some of the things that you do to be able to keep doing that?
09:00
Chris James
It's, it's easier said than done. I can definitely say that. But you just got to kind of be a goldfish in this industry and forget about it and move on really quickly, you know, and the more opportunities that I am working on at one time, the easier it is when, you know, one falls through, but maybe three others popped at the same time and, you know, focus on what's moving in a positive direction right now. You know, it's like, all right, that one's not for right now. I got three others that did agree to my proposal, and I'm moving forward in that direction now.
Why Industry Events Reset Mindset And Momentum
09:38
Chris James
And, you know, as soon as these things slow down a little bit, I have a note set or a calendar reminder to reach back out to that property manager a month after the start date that I know that the competitor is starting on to say, hey, how's it going? You know, how are they, are they delivering what you guys are looking for? You know, that's good.
09:58
Jack Jostes
I interviewed somebody on the podcast once who, when he lost a commercial account, would go and take pictures of it and send the client a before and after. So I don't know if I'm sure, you know, when you're driving around, oh, I want that community or I lost that community or whatever it is, you know, take a picture and be like.
10:20
Chris James
Hey, yeah, it's pretty plain to see, you know, and I can do that. I do that. I drive by ones that I haven't gotten all the time. And it's pretty glaringly obvious when an opportunity is still there, you know, like it's good for, for, it's good for them if that.
Using AI To Save Time On Proposals And Reports
13:11
Chris James
Oh, man. So a lot of the AI stuff, I think that I have been slacking on and I've been wasting a lot of my own time writing proposal descriptions, constructing emails to property managers. I really look forward to implementing that more and seeing how I can buy back some of my own time with AI. That's definitely big on the list.
KPIs, Transparency, And Motivating Crews
14:42
Chris James
Yeah. And I've only been to the, you know, I heard the keynote speaker, and then I've been to two seminars. So we're still kind of early in the conference. But key performance indicators was the other big thing that I. I noticed that we have them and the ownership team, and me as the operations manager, we have these kinds of conversations, but I think that we can motivate our crews and help everybody kind of feel like they're helping the company grow if we're more transparent about these key performance indicators and communicating with the crews, like, when, hey, guys, I want to let you know that we, you know, we hit these KPIs this month, or your crew did as a whole, and we appreciate that.
Growth, Discomfort, And Leadership Mindset
19:15
Chris James
I just kind of try to stay in the mindset of, like, anytime I'm uncomfortable, it's a good thing, you know, like, if I get too comfortable, I've probably stopped growing. We as a company have probably stopped growing. And, like, there needs to be that level of discomfort, and you have to be comfortable being uncomfortable. Cause a lot of the things that it takes to succeed in this industry are uncomfortable. Like, going and speaking in front of a HOA board that you don't even know after hours is uncomfortable. But it's how you build relationships with HOAs and boards and bring on that kind of clientele. So that's just, like, one example. But I try to always have gratitude for the discomfort, and that's not always my first thought. A lot of times I'm like, oh, crap, I don't want to feel this way.
Closing Thoughts And Where To Connect
21:43
Jack Jostes
Best luck, Chris James from Perfect Cut Landscaping. Where can we check out your website? Where can we network with you?
21:49
Chris James
So our website is 561lawn.com. You can find us on Instagram at Perfect Cut Landscaping. And then you could email me at chris@561-lawn.com Be happy to chat with anybody.
22:04
Jack Jostes
Well, thanks for coming on the Landscapers Guide podcast and exciting to hear you keep growing and selling and sticking with it.
22:12
Chris James
Absolutely. It's an honor and a pleasure and hope to do it again next year.
22:17
Jack Jostes
Yeah, let's do it.
22:17
Chris James
Yeah, absolutely. Thanks, Jack.