Landscape Maintenance Estimator
- LocationMashpee, MA, US
- Work typeOn-site
- Salary75k to 100k USD a year
- EmploymentFull-time
- Posted3 November 2026
- SourceOuterland Holdings, LLC's careers page (Paylocity)
Live checkFirst seen 5 days ago; still listed on Outerland Holdings, LLC's careers page 13 h ago.
At a glance
- Experience3+ years
Read from the ad by RoleFinder, with rules and an AI reading; the description is the source.
About the role
As the Landscape Maintenance Estimator, you’ll be a prospective client’s first experience with Outerland, and the person who earns their business. The estimator role blends consulting, sales, horticultural problem-solving and customer service: you’ll read a property, understand what the client values, design a maintenance plan that fits their landscape and their goals, and hand off a relationship our account managers are excited to inherit. New clients will walk away with the impression that we communicate, we care, and they’re a big deal to us.
Requirements
• Own inbound leads from first handshake to signed proposal, with follow-up that never leaves anyone wondering
• Walk properties with prospective clients — listen to their priorities, assess conditions, and communicate our value
• Build tailored maintenance plans around site conditions, takeoffs, client goals, company service offerings, and real budgets
• Put together accurate, detailed estimates and present proposals you can stand behind
• Lead the initial client meeting, set clear expectations, answer the follow-up questions, and close the sale
• Onboard new clients and hand off cleanly to their account manager — site notes, scope, and preferences all in one place
• Catch enhancement and upsell opportunities during site visits and pass them to the account management team
• Accurately, consistently, and proactively manage the sales pipeline within our CRM
• Track and manage sales performance against the sales budget
Qualifications
• 3+ years in sales or account management. Landscaping or green industry experience is preferred, but not required
• A working knowledge of landscape maintenance, plant material, and the problems properties tend to have — or the drive to learn it fast
• A consultative style: you ask good questions, listen more than you pitch, and communicate our value clearly to clients.
• Self-direction, ruthless attention to detail, and exceptional organizational skills
Compensation & Benefits
• $75,000 – $100,000 base salary based on experience
• Performance-based bonus opportunity
• Company vehicle, phone, and laptop
• Health, dental, vision, and supplemental insurance
• 401(k) with company match
Get open roles ranked against your CV
Add your CV once. RoleFinder ranks the open roles where you want to work, plus remote ones, against it, shows your best 12 with a one-line reason each, and emails you new matches once a week. The file is read once by AI and not kept; employers never see it.
Sign in with Google or email to start. How we handle your CV