Landscape Maintenance Estimator

Outerland Holdings, LLC; Mashpee (MA); On-site; USD 75,000 - 100,000; Full time

Benefits offered by this job

Company vehicle

Phone

Laptop

Health, dental, vision insurance

401(k) with company match

Job summary

Outerland Holdings, LLC is seeking a Landscape Maintenance Estimator to be the first point of contact for prospective clients, blending sales, horticultural problem-solving, and service design to craft tailored maintenance plans that fit client goals. You’ll read properties, communicate value, and set the stage for ongoing relationships.

You will walk sites with clients, present proposals, onboard new accounts, and diligently manage the sales pipeline in our CRM, while supporting account

Qualifications

• 3+ years in sales or account management; landscaping/green industry experience preferred but not required.
• Working knowledge of landscape maintenance, plants, and common property issues, or willingness to learn quickly.
• Consultative selling style: ask good questions, listen, and clearly communicate value.
• Self-direction, meticulous attention to detail, and strong organizational skills.

Responsibilities

• Own inbound leads from first contact to signed proposals with timely follow-up.
• Walk properties with prospects; listen to priorities, assess conditions, communicate value.
• Build tailored maintenance plans based on site conditions, goals, offerings, and budgets.
• Create accurate, detailed estimates and present credible proposals.

Skills

Sales & account management

Consultative selling

Client communication

Organization & follow-through

Tools

CRM software

Job description

Description

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