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.