Podcast Summary: Green Side Up – Ep 115: Selling Smarter: On-Site Sales, SOPs, and Running Lean

Release Date: March 12, 2026
Hosts: Jason Lee & Jordan Upcavage

Episode Overview

This episode of Green Side Up dives deep into the world of sales, SOPs (Standard Operating Procedures), and operational efficiency in landscaping and tree care businesses. Hosts Jason Lee, a seasoned landscaper, and Jordan Upcavage, a tree care expert, provide no-nonsense, field-tested insights on building smarter sales processes, implementing digital SOPs, dealing with lean crews, and balancing day-to-day business realities. Expect candid stories, practical solutions, and a transparent look behind the scenes as they walk through their own sales techniques and lessons learned.

Key Discussion Points & Insights

1. Landscaper Event Recap & Digital SOPs

[02:01 – 08:10] Jason: LeanScaper Operations Intensive

• Jason attended the LeanScaper operations event, gaining hands-on exposure to the Lana AI platform for SOP development.
• Lana AI: An AI platform tailored for landscapers, enabling creation, storage, and implementation of digital SOPs, checklists, and lean boards.
• Major Takeaway: The value lies in having “a place for all these processes and systems that we all have a hard time implementing, having a place for all these things to live” ([03:16], Jason).
• Eliminates paper checklists; uses tablets for real-time updates by crews.
• Still considering the investment due to current cash flow constraints, despite recognizing its potential for streamlining and micromanaging processes.

2. Real World Inventory & Accountability Challenges

[08:10 – 12:59] Jason & Jordan on Checklists and Tools

• Both hosts share stories of tools left at job sites—chainsaws, gas cans, and specialty equipment.
• Jordan underscores that checklists are useless if “the person filling them out gives a shit” ([09:22], Jordan).
• They credit their recent leaner crews and company culture with reducing these mishaps—a direct result of laying off underperforming employees and keeping only team members who take pride in their work.

3. Running Lean, Team Turnover, and Job Backlogs

[10:49 – 19:56] Jordan: Lean Crews and Employee Changes

• Jordan describes laying off six employees and losing others, paring the team from 23 down to 15.
• Candid about letting an employee go for “values that did not align” with the company—kept discreet but highlighting how culture impacts operations ([11:11], Jordan).
• Despite being "down to 15 employees and the work is increasing," he remains optimistic and motivated by finally having several days of work in the books after months of living “day-to-day” ([18:52], Jordan).

4. Adapting to Seasonal Uncertainty & Cash Flow Struggles

[19:30 – 21:10] Jordan's Perspective

• Jordan reflects on the stress of unpredictable schedules and how he's grown used to “waking up every morning and selling work just to stay afloat.”
• The segment encapsulates the psychological grind of seasonal business: “After like four months of that... I just kind of got used to it...it’s normal” ([20:11], Jordan).

5. On-Site Sales: Process Walkthroughs

A. Design/Build Landscaping Sales Process

[27:51 – 46:02] Jason’s Process

• Pre-Visit: Office staff calls clients to confirm appointments, usually 1–2 days in advance.
• On Arrival: (Ideally) calls client en route; avoids entering clients' houses, preferring yard walk-arounds for practical access reasons.
• Discovery: Begins by clarifying client needs, their goals, and how they use the space (fire pits, seating areas, etc).
• Site Analysis: Details checks for utilities (noting recent costly mishaps with cable lines under mulch), irrigation, drainage, and other logistical hurdles.
  • "[Cable lines] under the mulch...cost us $500 each in recent months." ([31:25], Jason)
• On-the-Spot Design: Uses photos and markup tools (Company Cam) or physical spray paint for quick sketches and concepts onsite.
• Pricing: For smaller jobs, aims to provide an exact quote on the spot (“to the penny” if possible); for more complex jobs, gives a confirmed range and follows up as soon as possible.
• Client Education: Emphasizes setting expectations around plant variability and the likelihood of last-minute species swaps, always noting “What plants don’t you like?” to align designs with preferences.

B. Tree Care Sales Process

[47:37 – 60:01] Jordan’s Process

• Lead Intake: All leads logged in SingleOps with mandatory “lead source” field for accurate tracking.
• Appointment Scheduling: Schedules in “between time” blocks (e.g., 11–12), not fixed times.
• Client Communication: Courtesy call on approach, considered essential.
  • “Hey Doug, this is Jordan, Independent Tree. Just wanted to give a courtesy call… I’m about eight minutes away.” ([47:55], Jordan)
• On Arrival: Mindful parking, avoids blocking driveways or walking over roots; shows professionalism even in the little things.
• Fact-Finding: Starts with open-ended questions: “How can I help you? What are your concerns? What are your goals?”—never assumes the solution is obvious.
• Education First: Explains tree species, health, and risks, often debunking common myths (e.g., what dead branches really mean).
  • “Dead branches are normal....Now if we find dead branches up at the top...something’s not right. That’s root degradation due to fungus or construction compaction.” ([48:47], Jordan)
• Proposals & Closing: Recaps the plan verbally, then typically writes up and emails the proposal from the driveway—used to close on the spot but now finds email follow-ups suffice.
• Guidance v. Pressure: Emphasizes client empowerment: “I very much care that I have given you all the information and education so you can make an informed decision. That’s what I very much care about.” ([52:38], Jordan)

6. Adaptations for Growth and Efficiency

• Both hosts are actively pushing toward more on-site closes for efficiency, using tools like digital sketch-ups, product images in proposals, and immediate proposal generation.
• The importance of education, transparency, and minimal pressure in their sales approach is repeatedly emphasized.

Notable Quotes & Memorable Moments

• On Digital SOPs:
  “All these things that we’re already doing on paper…now through Leanscaper and Lana AI, this is something that we can easily have the guys pull up on their tablets. Check, check, check. And then…real time shows up. If we log in, we can see everything done in real time.”
  — Jason, [04:30]

• On Employee Culture:
  “Checklists only work if the person filling them out gives a shit. Now, if you have a person to begin with that gives a shit, you’re probably less likely to leave your shit everywhere.”
  — Jordan, [09:22]

• On Running Lean:
  “I have the fewest number of employees I’ve had in a long time…But I’ll tell you, the values of this individual did not align with the values of independent tree service…So I’m down to 15 employees right now, Jason, and the work is increasing.”
  — Jordan, [10:49, 15:26]

• On Business Anxiety:
  “It’s been so day to day since end of October that I’m now very callous and numb to it…After like four months of that being my life, I just kind of got used to it. And it’s normal: better sell something or we’re twiddling our thumbs…”
  — Jordan, [20:11]

• On Sales Process—Tree Work:
  “I don’t care what the client chooses to do. I very much care that I have given you all the information and education so you can make an informed decision. That’s what I very much care about.”
  — Jordan, [52:38]

• On Jobsite Etiquette:
  “I try not to go through [the customer’s] house…Because me going through your house actually takes away from my knowledge of your property…I still need to then scout around and look at our access via the sides of your house to get to the backyard.”
  — Jordan, [36:16]

Segment Timestamps

• Jason’s LeanScaper event/SOPs deep dive: [02:01 – 07:12]
• Checklist reality & tool inventory stories: [08:10 – 12:59]
• Team reductions & company culture: [10:49 – 19:56]
• Selling with barely any backlog / Cash flow stress: [19:30 – 21:10]
• Landscaping sales script, step-by-step: [27:51 – 46:02]
• Tree care sales script, step-by-step: [47:37 – 60:01]
• Comparing tree/landscape sales cycles & proposal tactics: [43:58 – 46:02]
• Closing thoughts, future episode teasers, and shout-outs: [60:01 – 64:01]

Key Takeaways

• Digital tools—from AI-driven SOPs to instant jobsite markups—are shaping efficiency, but their value depends on staff engagement and culture.
• Running a lean operation intensifies the importance of each team member’s buy-in, accountability, and pride in workmanship.
• The sales process for both landscaping and tree care is rooted in open communication, practical site analysis, client education, and, ideally, expedient quoting/closing.
• Both hosts see follow-up, client empowerment, and continuous process improvement—not high-pressure “closing”—as the true keys to growing sales and securing repeat/word-of-mouth business.

Connect & Upcoming Topics

• Next week, the hosts will tackle follow-up & scheduling, and provide updates on business development manager initiatives.
• For questions or to reach out: greensideuppodcastmail.com, or social media (Instagram/Facebook).

End Note from Jason:
"Keep working hard so you can play even harder, and keep the green side up." ([63:25])