JOB DETAILS

Landscape Maintenance Estimator

CompanyOuterland Holdings, LLC
LocationMashpee
Work ModeOn Site
PostedAugust 6, 2026
About The Company
Outerland is a team of dedicated outdoor professionals committed to delivering a high standard of service, through our focus on the client experience. The space we operate in is busy with players of all sizes with varying definitions of landscaping quality - we define success on a different basis. We stand apart by prioritizing what is routinely considered secondary to the service provided. We focus on people first, our clients and our employees, the experiences of both, and consistently deliver at a high level. Outerland is committed to cultivating landscapes with care. We start by prioritizing the care of our team—nurturing their growth and nourishing their aspirations. After all, happy, fulfilled, people are the true source, and direct result of, great service. With this always in mind, our behaviors reflect this priority. We focus on assembling good people who come together as a team to provide an unrivaled experience for our clients every time, because we know that experience is everything.
About the Role

Description

 

We’re looking for a Landscape Maintenance Estimator to be the person prospective clients meet first and are excited to work with. It’s part consulting, part sales, part horticultural problem-solving: you’ll read a property, understand what the client cares about, design a maintenance plan that fits their goals and their budget, 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. 


What You’ll Do

  • 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, spot what they haven’t noticed yet
  • Build tailored maintenance plans around site conditions, client goals, 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
  • Keep leads, site visits, and proposals current in our CRM
  • Track and manage your performance against the sales budget

What You Bring

  • 3+ years in sales or account management. Landscaping or green industry experience is a plus, not a requirement
  • A working knowledge of landscape maintenance, plant material, and the problems properties tend to have
  • A consultative style: you ask good questions and listen more than you pitch
  • Self-direction, ruthless attention to detail, and the organizational skills to keep an up-to-date pipeline

What We Offer

  • $75,000 - $100,000 base salary, depending on experience, plus a performance-based bonus
  • Company vehicle
  • Company-provided phone, laptop, and every tool you need to do the job right
  • A crew that delivers on what you sell  so you can promise confidently and sleep well
  • 401(k) matching program
  • Health, dental, and vision insurance and other supplemental insurance
Key Skills
SalesAccount managementLandscape maintenanceHorticultural problem-solvingConsultative sellingEstimatingProposal writingClient onboardingCRM managementBudget managementCommunicationAttention to detailOrganizational skillsPlant material knowledge
Categories
SalesConsultingConstructionEnvironmental & SustainabilityManagement & Leadership
Benefits
401(k) matching programHealth insuranceDental insuranceVision insuranceSupplemental insuranceCompany vehicleCompany-provided phoneCompany-provided laptopPerformance-based bonus
Job Information
📋Core Responsibilities
The estimator will manage inbound leads, conduct property site visits, and design tailored maintenance plans to meet client goals and budgets. They are responsible for closing sales, onboarding new clients, and ensuring a smooth transition to the account management team.
📋Job Type
full time
💰Salary Range
$75,000 - $100,000
📊Experience Level
2-5
💼Company Size
32
📊Visa Sponsorship
No
💼Language
English
🏢Working Hours
40 hours
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