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Ep 114. Scripts, Systems, and Sexy Proposals: Upgrading Your Sales Process - Green Side Up | Wave AI Podcast Notes

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Ep 114. Scripts, Systems, and Sexy Proposals: Upgrading Your Sales Process

Green Side Up

Thu Mar 05 2026

Summary

Green Side Up – Ep 114

Scripts, Systems, and Sexy Proposals: Upgrading Your Sales Process
Hosts: Jason Lee & Jordan Upcavage
Date: March 5, 2026

Episode Overview

In this episode of Green Side Up, Jason and Jordan dive deep into the nitty-gritty of sales processes for landscaping and tree care businesses — from the first inbound call to sealing the deal. Prompted by a listener's question, the hosts candidly break down their approaches to scripting, proposal writing, vetting clients, and leveraging modern tools and technology. In true Green Side Up style, their advice is delivered with humor, real-world stories, and actionable takeaways for business owners at all stages.

Key Discussion Points & Insights

1. The Origin Story (Listener Q&A)

Listener Nick from Irish Landscaping inquires about creating and implementing an effective sales process.
Jason: “He asked if we had covered… taking our sales process kind of from inbound phone call to close of sale.” (03:10)

2. The ‘Inbound to Sale’ Process – Laying Out the Steps

Jordan outlines his current (albeit unwritten) sales process, built more out of necessity than formal planning.
Jordan’s nine-step process (06:38 – 09:58):
1. Client calls office for a quote (scheduling handled by his sister, Christie).
2. Arborist calls client before the appointment.
3. On-site scope of work developed; proposal may be delivered and closed on site or via follow-up.
4. Automated email follow-ups at 3 and 7 days via SingleOps software.
5. Client accepts proposal online; automated thank-you email sent.
6. Job scheduled; client notified.
7. Crew shows up and performs work.
8. Post-job quality check call.
9. Invoice sent and payment processed; receipt delivered by email.

Jordan (on proposals):
“2020 to 2024 made us spoiled and lazy… decreasing the incentive to work a little harder on the sales closing end.” (08:42)

3. Scripting the First Call — Role-Play Demo

Jason and Jordan perform a role-play of a sales call that showcases Sky Frog Landscape’s script and approach (13:20 – 24:25).
- Key script elements: Asking if the caller is a previous client, where they heard about the company, budget discussions, vetting availability, preliminary screening of project size and client intent.
- Use of humor and relatable language adds approachability to the process.
- Questions about irrigation, fertilization, current maintenance provider, and decision-makers are included.

Jordan (as a potential client):
“My in-laws judged me so I wanted to see if you could make me look like I deserve their daughter.” (14:29)

Jason (on minimum project size):
“If we're going to come show up at your house, this is what it's probably going to cost… currently at like $1,500.” (11:45)

Efficiency Matters: Most “real” calls are much shorter than the demo, with staff like Michelle getting all needed info in under three minutes (25:23).

4. Client Vetting, Budgets & Setting Expectations

Vetting for Fit: Project minimums are stated early to avoid time wasted on “tire kickers”.
Website Transparency:
- Displaying rough pricing tiers on the website helps set expectations and reduce mismatches.
- “You have small landscape projects starting at five grand… you’ve groomed me into… spending 8 grand at a minimum.” (27:47)
- Benefit: Clients who follow through have already self-selected, leading to higher-quality leads.
On Handling Budgets:
- Realistic conversation about clients’ willingness to state a number.
- Sometimes, early budget ballparks save the company from wasting site visits.

5. Design Fees & Managing ‘Free Work’

Nick’s Dilemma: Did a design before collecting a fee; client ghosted him for another landscaper.
Best practice: “Get the money before you do the work on the design.” (32:01)
Design as a Profit Center (or Not): Depending on market and project size, design fees vary from negligible to substantial.
Jason: Prefers to close small jobs on the spot with minimal sketches—keeping proposals simple unless a full design is warranted.

6. Sexy Systems: Proposals & Communication Tools

Live Switch and AI tools are revolutionizing work order creation, proposals, and internal communication.
Jordan’s Example:
- Videotaped walkthroughs and job explanations transcribed into comprehensive work orders (36:25+).
- For complex, high-touch proposals (e.g., “South Tampa mansion”), meticulously documents client requirements, uploads video, links all equipment used—delivers a “sexy” proposal that justifies the price and sets clear expectations (40:33 – 45:28).

Jordan:
“It is so anal retentively covering my ass… I have captured everything she couldn’t. We can’t lose. We’re either going to make money or I’m not going to do the assignment.” (44:41)

AI in Sales Ops:
- Tools like ChatGPT + recording software accelerate proposal development and ensure nothing is missed.

7. Scaling, Referrals & Marketing Spend

Client Story: Andrew (Nebraska arborist) consults Jordan on marketing and sales growth.
- Spends too much on digital marketing relative to revenue.
- Recommendation: Focus more on grassroots referrals and direct asks for Google reviews than expensive ad spends.
- Jordan’s advice: “Don’t make it a gimmick… be honest and genuine.”

Jordan:
"Cut the crap of incentives and gimmicks… if you think I deserve it… I’d appreciate a referral and a hearty thank you." (49:14)

Technology Differentiation:
- Being first in your market with video or AI-enhanced proposals creates a sales edge.

8. Real Talk on Process Limitations & Future Topics

The hosts admit:
- Much left uncovered—deeper dives into later sales stages ahead.
- Invite further listener questions and feedback (53:46).

Jason:
“If you have anything that you think we should go more in depth on… there’s a lot more that goes into before we close the job that we don’t have time to cover today.” (53:46)

Plans for the next episode:
- A possible series on the customer-facing sales process.
- Focus on refining the client experience post-script.

Notable Quotes & Memorable Moments

On the importance of scripts:
- “The ultimate goal is to try to vet the client to some degree to make sure that they’re going to be a right fit for our business. Screen out the tire kickers...” (11:05 – Jason)
On handling difficult project requirements:
- “I was pricing the job and I deleted the price and added an extra thousand dollars right when she goes, ‘No, sir, you cannot touch those green branches.’” (40:41 – Jordan)
On proposal “sexiness”:
- “Speed kills and sex sells. So get your... proposals done on the spot. Have the robot do it, and bam.” (52:00 – Jordan)
On harvesting the day:
- “We are winking and grinning at each other because we have guns on our hips and they're loaded and we're going to go out and kill...we're going to harvest this day. We’re going to thank this day for the energy and the life it gave us.” (55:31 – Jordan)

Key Timestamps

00:05–04:10: Episode opening, listener context, and topic introduction
06:38–09:58: Jordan’s 9-step sales process overview
13:20–24:25: Role-play demo of the inbound call script
25:23: Efficient call handling and real-world cadence
27:47–29:05: Impact and philosophy of transparent pricing online
30:33–34:08: Discussion of design fees and Nick's payment dilemma
36:25–45:28: Applying AI/video tools to proposals and work orders
47:08–52:00: Referrals, scaling operations, grassroots vs. digital marketing, and Live Switch advantage
53:46–55:10: Wrapping up, listener Q&A, and teasing future topics
55:26–57:32: Inspired sign-off and “harvesting the day” metaphor

Takeaways for Listeners

Have a script and process—even a basic one—to streamline and qualify leads.
Post project minimums and ballpark prices online to set expectations and filter prospects.
Collect fees for design work up front—don’t work for free.
Leverage AI and video tools for clarity, speed, and “sexy” proposals.
Focus marketing on authentic referrals and reviews before overspending on digital ads.
Iterate: There’s always another stage to improve in your customer’s experience.

Missed the episode? This summary gives you the “real dirt”—but the full banter, stories, and irreverent humor make it even richer for the entrepreneurial soul in landscaping and tree care.

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Transcript

A (0:05)

Welcome to Green side Up, the perfect podcast for small business entrepreneurs looking to cultivate success in the landscaping and tree care industry. Join Jason Lee, a seasoned landscaper, and Jordan Upkavage, a true tree whisperer, as they share their wealth of experience and insights to navigate the challenges of growing your business. Get ready to hear real life stories, practical solutions, and invaluable advice that will empower you to thrive amidst the chaos of entrepreneurship. And now, let's keep the Green side Up with your host, Jason Lee and Jordan Upkevage. Jordan, good morning.

B (0:49)

Did it again. We both win at the same time.

A (0:56)

All right. The rock, paper, scissors short. All right, go.

B (0:58)

Rock, paper, scissors, shoot.

A (1:00)

Scissors, shoot.

B (1:01)

Did you throw paper?

A (1:03)

I threw. Yeah. Well, I threw her scissors.

B (1:05)

Oh, then I beat you. So I get to go. Buenos tardes, Yakimo Lee.

A (1:12)

Good morning, Jordan.

B (1:13)

That was my first rock, paper, scissors of the day.

A (1:16)

Yeah, me too.

B (1:18)

Well, Jason, it's good to have you. It's good to be had at the same time. The last recording we did was last week, and we debriefed the landscape radio, which was so much fun, wildly successful event. And it's interesting. I've had a number of people in Tampa say hoes landscape rodeo. Whether it was the grassroots talking to the local FNGLA of Tampa, or landscapers and hardscapers in Tampa, or listeners, people have said, how was the landscape radio? I was like, huh? How the hell did you know? Like, you texted me, think about the crawfish boils. Oh, yeah, yeah, yeah, yeah. Anyways, that was. That was tons of fun, and it was good to. To debrief it. So, yeah, to kick off our week here, Jason, you had some communication with a listener of ours, someone who we've met at a trade show. So go ahead and butter that toast before we eat it.

A (2:23)

Yeah. So Nick with Irish Landscaping, who is over in the Deland area, Greater Deland area. Imagine, he services. We met him during Rob Murray with Intrigue Media's talk last year at the landscape at the landscape show in Orlando, which is generally around the third week in August at the Orlando Convention Center. And we met Nick after the seminar, and then we talked to him for probably 10 or 15 minutes at the hotel bar later and got to know him a little bit. But he. He and I had been texting about something before the landscape rodeo. And then he called me the other day because he was navigating some. Anyway, some sales issues. What do I charge for landscape designs? How do I approach this scenario, that scenario? And he asked if we had Covered any, I guess, specific episodes of taking our sales process kind of from inbound phone call to close of sale. And I told him we've talked about a lot of different sales things, but probably not covering that. So I figured that'd be a great thing to talk about today.

B (4:10)

I'm in. I'm very excited is not the right word, but I'm, I'm intrigued to know. I'm. I'm curious to know how you're going to answer this question because you have spent more money on coaching, therefore you likely have set aside more time than I have to do something about it or put something in writing. So I don't have a written sales process or a written script over the phone. Probably should, but I don't in a roundabout way. We have a rough outline of a written script for the inbound phone call. And the reason we have that is we got very busy early last year and the phone volume was too much for one person to manage. So we hired an answering service named Ruby. Ruby advertises on a lot of XM talk radio stations. And I've heard about Ruby for years and I said, screw it, I'm going to hire Ruby. So in the process of onboarding Ruby, we outlined a roug sketch, a rough script, a skeleton of what the person over the phone would do. And my sister Christie helped do a lot of that. So we kind of have a rough script from doing the Ruby deal, but nothing that's like in concrete. And then the, the sales process, I don't have one written down, but we, Jason and I, you, you and I both went to Tony Bass's Profit Builder in January of this year. And as part of Profit Builder, before you go, there's paperwork that you have to fill out. There's some homework assignments, and it's the confidential Profit Builder Business assessment questionnaire prepared by Tony Bass. And I have it right here. And there's a number of questions that you would answer for Tony to get to know your process and get to know you a little bit better. For instance, do you prepare an annual budget? If no, why not? If yes, what month of the year do you do it in? How do you arrive at a price for a job? Describe precisely the entire process and there's a number of questions of what do you expect to receive from a consultant or how do you hope to benefit from hiring a consultant? What topics do you read or study on a regular basis? But the question here that I think pertains to the topic is how often do you communicate with your customers? Describe exactly how you do it. So this kind of touches on that and this is the only time I've written it down and I have nine bullet points and I have one the client calls into the office to get a quote. Christy, my sister schedules the Arborist appointment with the client or they pay the phone or they play the phone call and voicemail game until contact is made. Number two Arborist usually calls the client when on the way to the property. That's the when we're on the way to the scheduled time.

B (7:54)

I just wanted to let you know I'm on the way to your home. It's Tuesday between 10 and 11. Number three tree evaluation and scope of work description is developed either in person with the client or over the phone for a mobile walkthrough. If the client is not present proposal sent via email occasionally, the deal is closed on site verbally with the paperwork to follow. Number four if the job is not closed within three days, the software, which is single ops, sends an automatic follow up email and again a second and final follow up cost. Seven days after proposal submission if not yet accepted. The past six months I have turned up the phone call proposal follow up due to necessity. 2020 to 2024 made us spoiled and lazy with a plethora of work, decreasing the incentive to work a little harder on the sales closing end. Number five Client clicks the accept proposal button on the emailed proposal link. The software then sends an automated thank you message acknowledging the proposal was accepted and informing them the team would follow back with a scheduled work date. Number six Salesman schedules the work in the crew calendar, sends an email to Christy with the job schedule. Christy then emails and calls the client with the job scheduled date and this is not what you asked but I'm going to finish it out. Number seven Cruz shows up at the scheduled time and performs the work. Number eight the day after the work is performed, the salesperson calls the client for quality control and customer satisfaction. Number nine Christy then sends an invoice via email. Once the payment has been processed via check to the PO Box ACH Transfer or online credit card, the customer receives an automated paid invoice via email. So that's the broad picture process that the customer would experience. Maybe that touched on a little bit on what you wanted to talk about. Happy to elaborate more on one of those nine points, but that was just me taking some time to write down the process that we have. Having never written it down before.

A (25:41)

sometimes. I mean, we'll get, we'll get real budgets. We'll get, you know, I don't want to spend more than five grand. And some of it, you know, we, we screened the customer the other day. You know, he wanted to do an Artscape project and a pirate area and whatnot. You know, only wanted to meet after hours, didn't want to meet during the day, which is generally a red flag for us. And we, we try not to do that anymore when we might break an exception. But it's. We're of the opinion now, you know, if you can't take, if you don't value our service enough to anyway take off of work or meet sometime during that, you know, 8, 10, 12 or 2 or. I think it'll even go up to 4 o' clock as the latest appointment, but definitely we're not doing, we're doing very few. I would consider it a handful of after five o' clock or weekend appointments a year. But when he had somebody that was, you know, requesting and not maybe not demanding, but requesting an after hours consultation. And so, you know, Clayton just, he's like, what's his budget? So, you know, Michelle's like three to seven grand. But he preferred not to spend more than five. So Clayton did a couple of rough. Anyway, rough estimates or rough ballparks to give the guy. So, you know, he told him, hey, this, this size five, you know what area you're looking for? He told him the area. He's like, all right, well, this falls into. He's like, could probably be between 8,500 and 9,000. So I'm pretty sure the guy, you know, decided not to have us come out. Which means, which is great because we just saved the. Yeah, save the trip out with not hitting it. But, you know, a lot of people say between 5 and 10, between 10 and 15. We've had quite a few people, you know, go to the pricing page and say that it was great, you know, to see, see what's there. And then who knows who goes and looks at it and scares them away. But for the people that look at it and see it and then call us, like, those people are vetted, like they've already gone through, you know, before they call us, they've already, they've already gone through the process and made a decision to call us, which means that they're probably not calling anybody else.

B (40:41)

Big son of a. And this, the top of this thing has been dead for more than a year. Why it's dying, I don't know. And then now 90% of this thing is dead and it needs to be cut down. So my customer walks me over to the neighbor. The neighbor, although you would assume has a pile of money being in this same area does not have the level of property maintenance that is a custom. Like they have old crappy trees that aren't cut down yet and they have nice potted plants and nice house. I mean the dirt is worth millions of dollars. Just the dirt of the lot. But anyway, so we're looking at this removal and it has to be done via climbing because there's no way to get in there. I have a four foot wide gate that, that I have to get the debris out. And there's adjacent Weeping podocarpus that she doesn't want damaged because it blocks the corner. Why she doesn't want to look at the corner. I was like we can do that. And I said, but you see these low branches that we are having to duck under right now that we looking at this are having to duck under. I would like to raise these branches up and maybe to 8ft so I can get an articulating wheel loader to carry all of the brush out. Oh no, no sir, you can't. No, you cannot do that. You cannot cut Any branches off of this tree. It's like, okay, so we going to duck as we hand carry these branches out. We are going to duck as we move, moving dolly log by log. And then she goes, well, you're going to put plywood down, right? Yes, ma'. Am. We're going to put plywood down across her grass, through the gravel bed, through this little tiny gate. And it was so funny when she said, you can't cut those branches. As I had my notes open in my phone. I was pricing the job and I deleted the price and added an extra thousand dollars right when she goes, no sir, you cannot touch those green branches. Like okay, boop boop, boop, $1,000 more. I see how this is going to go. And she goes, when you send the proposal, can you tell me exactly what equipment you're going to be using, how many guys are going to be here, how long it's going to take? And can you document everything that you told me about the branches being preserved and a plywood Runway and that you have to go through this double gate and you're not scratch the doors? I said, absolutely, I can do that for you. I was, yes, man. And the whole time this call was going on, I'm thinking to myself, I don't want to work for this person. And it's getting progressively more expensive. Like we have almost doubled the cost that I started at after this whole horse and pony show. So I pull up live switch and I videotape. This is the tree of subject. This is how we're going to do it. We're going to climb everything. We're going to descend branches here, this adjacent Podocarpus. We're not going to touch it all. We're going to preserve all of these low branches so it is untouched. When we're done, we're going to build an 18 sheet long plywood Runway through here. We're going to move this potted plant with irrigation that's built in on the bottom. The wheel loader can move logs only. All brush. Hand carried grapple truck in the driveway. Two sheets of plywood under the debris. Grapple zone to not scratch the driveway. Everything recorded and then transcribed into the work order. And then I went and pulled. We're going to use a Nifty Lift. A nifty lift SD64 and pulled the link from the Nifty Lifts website so she could see it. I'm going to use an Avant 528 or a giant G2200 extra. And link, link. And I'm Going to use a Kenworth pack Mac Grapple truck link. And in the proposal was the written work order, links to the video, links to every piece of equipment that I'm going to use on this job. And I sent the proposal same day, which was yesterday. So we'll see if I get it. In a way I don't want to get it but if I do it is so anal retentively covered my ass of I have captured everything she couldn't. We can't lose. We're either going to make money and we're going to I was going to do this job in one day. It just turned into two days just to give myself more room of nice and tiny little branches hand carry it. We're not going to go do this job and kill ourselves. We're going to have a great day or great two days doing this job and we're going to make some money or I'm not going to do the assignment. So thank you Switchy for covering my ass and helping me write a novel of a proposal outlining exactly what would happen.

B (49:14)

too much, in my opinion, on what should be the price to pay. It was like, holy schizo. Seriously, dude. I was like, oh my God. Well, if you're paying that much, let's just put it on pause. Like, let's spend half of that amount of money and let's look into other ways of doing things. Like, and we talked all about the Google reviews and if you can get it, the, the crew leader, the sweaty person, we can do, you know, that close the Google review in person. Let's start hammering that. Let's not be afraid to ask for a direct referral. If you have a customer that you did a great job, ask them directly. Hey, I'm starting out my business. I'm trying to grow this business. I'm trying to run A tight budget. I'd really appreciate it if you have a referral for me. A, a neighbor, a family member, anybody that you think we would be a good fit for, please give them my phone number. I'd love to earn their business. And I said, don't make it a gimmick. Don't make it a rebate. And you get a gift card and you get a hundred dollar rebate for your referral. I said, screw that, man. Make it honest and genuine. Give if you think I deserve it. And I'd be a good fit. I'd appreciate a referral and a hearty thank you. And I'm going to be your tree guy forever. And do it because we deserve it. If we don't deserve it, don't give me the referral. And I said, cut the crap of incentives and, and gimmicks. And I was like, your marketing budgets through the fricking roof, dude. I said, I kind of went back to like grassroots of like, let's simmer that shit down and let's find another way, join a fricking Rotary club or something. But it was too high. And I was like, you should spend less money than that and that. I said, if you want to spend the same amount of money, you hire Intrigue. If you want to spend half the amount of money, hire Intrigue and they're going to do a better job for you. But I was like talking them off the ledge on think of a older school, grinding way to do it first if you are in this very new stage of business. Now, maybe I gave him awful advice or maybe I didn't, I don't know. But that was just my personal take on it. And then we talked about software and what software he uses. He knows that we use single ops. And I told him that it works for me. I like it. It integrates payments and he uses whatever software. And then I said, bro, have you heard about Live Switch? And he goes, no, what are you talking about? And then I gave him the whole spiel about it, about how for me, it helps, like the crew, my communication with the crew leader. I don't ever have to go there again. And they don't have to call me. Well, they still need to call me, but it cuts out a lot of descriptive language I would have to use explaining what I want done. When the crew leader watches the video, it's in the crew notes. It makes it so easy. And I said the main thing, Andrew is no other arborist in my area is using Live Switch. So no other people are giving a video link to what's going to be done and how it's going to be done. So that means I am delivering the clearest, most concise, most commutative, the sexiest proposal is going out from my hands and nobody else is using it. It's like, bro, it's going to cost you like 160 bucks a month. So it's a disposable amount of money. For the tens of thousands of dollars that you're spending in marketing, just buy live switch and give it a shot and your stuff will instantly look sexier and speed. Speed kills and sex sells. So get your. Get your proposals done on the spot. Have the robot do it, and bam. So anyways, that was super cool talking to Andrew. And Andrew, I so very much appreciate you listening to us for the 45 minute phone call we had in my backyard on like Monday or Tuesday afternoon. It was super fun. And you have direct cell number. So please give me a call, shoot me a text, because you're in Nebraska and I'm in Florida. I have no secrets and I will tell you everything I possibly can.