Estimator & Landscape Designer

Remote Landscape Estimator & Designer — Full-Time, Exclusive

Company:
Skyline Exteriors is a fast-growing landscaping design and build company based in Skokie, Illinois, serving Chicago’s north side and northwest suburbs. We work with high-end residential clients, commercial properties, HOAs, and municipalities. We are targeting $10M in revenue this year and building a world-class remote operations team to get there.

What You Will Do
You will own the estimating and design function end-to-end. This is not a support role — you will be the person responsible for
producing accurate, professional, and margin-protected estimates and landscape design plans that win jobs and protect our profitability.

Your core responsibilities are as follows. You will receive client scope information from our appointment setters and account managers, then produce detailed cost estimates for landscaping design and build projects — including materials, labor hours, plant selections, and hardscape elements. You will create 2D and 3D landscape design renderings using tools such as SketchUp, AutoCAD, Vectorworks, DynaScape, or equivalent. You will select plants appropriate for the Illinois climate and USDA Hardiness Zone 5b/6a, with knowledge of native species, seasonal interest, soil requirements, and maintenance profiles. You will ensure every quote maintains a gross margin of at least 50% and a labor variance within 5% of actual. You will track revision counts and aim to close quotes within two revisions. You will flag any scope gaps or under-scoped items before a quote is submitted. You will participate in weekly review calls with our estimator and GM.

Performance Standards (Tracked in Our Operating System)
These are the exact KPIs you will be measured against from Day 1:
KPI Target:
Gross Margin per Quote ? 50%
Labor Variance (estimated vs. actual) ? 5%
Under-Scope Rate ? 2%
Average Revision Count per Quote ? 2
Rework Rate (jobs requiring re-do) ? 3%

What We Are Looking For
1. Education and Background. You are a licensed architect, civil engineer, landscape architect, or have a degree in horticulture,
environmental design, or a related field. You have at least 2 years of hands-on experience producing estimates and design plans for landscaping or exterior construction projects. Experience with US-based clients — especially Midwest or Illinois — is a strong advantage.

2. Technical Skills. You are proficient in at least one professional design tool (SketchUp, AutoCAD, Vectorworks, DynaScape, or similar). You can produce clean, client-presentable 2D plans and 3D renderings. You know how to build a line-item estimate with material costs, labor hours, and markup. You are comfortable working in Google Sheets, Excel, or a CRM-based estimating tool.

3. Horticulture Knowledge. You understand plant selection for USDA Zone 5b/6a (Chicago area). You know which plants thrive in Illinois winters, which are native, and how to specify them correctly in a design. You can recommend plant palettes that are both visually compelling and low-maintenance for upmarket residential clients.

4. Remote Work Capability. You have a reliable internet connection of at least 20 Mbps. You have a dedicated, quiet workspace. You are available during US Central Time business hours (8 AM – 5 PM CST), Monday through Friday. You have a backup power and internet solution. You are responsive on Slack and email within 15 minutes during work hours.

5. Commitment. This is a full-time, exclusive position. You will not take on other clients or freelance work while employed with Skyline. We are building a long-term team and expect the same commitment in return.

What We Offer
- Full-time remote position with stable, long-term employment
- Competitive salary based on experience (state your expected rate in your application)
- Direct access to our GM and operations team — no bureaucracy
- Clear KPI-based performance reviews with raise eligibility tied to results
- Work on real, high-value projects ( 500K+ residential and commercial installs
- A company that is scaling fast and rewards people who perform

How to Apply:
Send the following to be considered. Applications without all four items will not be reviewed.
1. Your updated resume or CV
2. A portfolio of at least 3 landscape design projects you personally worked on (PDF or link)
3. A sample estimate or cost breakdown you produced (can be anonymized)
4. A 2–3 sentence answer to this question: “A client wants a full backyard redesign in Naperville, IL. What are the first three plants you would consider specifying and why?”

Subject line: “Landscape Estimator + Designer — [Your Name]”